Document:

<PAGE>

                                                                   Exhibit 10.14

                            STOCK PURCHASE AGREEMENT

                                     among

                              SYNAPSE GROUP, INC.,

                                      and

                          THE PURCHASER NAMED THEREIN

                         ______________________________

                               Dated May 17, 2000

                         ______________________________
<PAGE>

                               TABLE OF CONTENTS
                               -----------------

<TABLE>
<CAPTION>
                                                                Page
                                                                ----
<S>                                                             <C>
ARTICLE 1  DEFINITIONS.........................................   1

1.1   Definitions..............................................   1
1.2   Accounting Terms; Financial Statements...................   5

ARTICLE 2  PURCHASE AND SALE OF PURCHASED SHARES...............   5

2.1   Purchase and Sale of the Purchased Shares................   5
2.2   Closing..................................................   5

ARTICLE 3  REPRESENTATIONS AND WARRANTIES
      OF THE COMPANY...........................................   6

3.1   Corporate Existence and Power............................   6
3.2   Authorization; No Contravention..........................   6
3.3   Governmental Authorization; Third Party Consents.........   6
3.4   Binding Effect...........................................   6
3.5   Litigation...............................................   7
3.6   Capitalization...........................................   7
3.7   Consolidated Financial Statements........................   8
3.8   No Material Adverse Change; Ordinary Course of Business..   8
3.9   Taxes....................................................   8
3.10  Disclosure...............................................   9
3.11  Private Offering.........................................   9
3.12  No Default or Breach; Contractual Obligations............   9
3.13  Broker's, Finder's or Similar Fees.......................   9

ARTICLE 4  REPRESENTATIONS AND WARRANTIES
      OF THE PURCHASER.........................................   9

4.1   Existence and Power......................................   9
4.2   Authorization; No Contravention..........................  10
4.3   Governmental Authorization; Third Party Consents.........  10
4.4   Binding Effect...........................................  10
4.5   Purchase for Own Account.................................  10
4.6   Investment Experience; Information.......................  11
4.7   Broker's, Finder's or Similar Fees.......................  11

ARTICLE 5  CONDITIONS TO THE OBLIGATION OF THE
      PURCHASER TO CLOSE.......................................  12

5.1   Secretary's Certificate..................................  12
5.2   Stockholders Agreement Amendment.........................  12
5.3   Registration Agreement Amendment.........................  12
5.4   Waiver...................................................  12
5.5   Purchased Shares.........................................  12
5.6   Consents and Approvals...................................  12
</TABLE>

                                       i
<PAGE>

<TABLE>
<S>                                                              <C>
5.7   Receipt of Consolidated Financial Statements.............  13

ARTICLE 6  CONDITIONS TO THE OBLIGATION OF THE COMPANY
      TO CLOSE.................................................  13

6.1   Payment by the Purchaser.................................  13
6.2   Stockholders Agreement Amendment.........................  13
6.3   Registration Agreement Amendment.........................  13
6.4   Waiver...................................................  13
6.5   Consents and Approvals...................................  13

ARTICLE 7  INDEMNIFICATION                                       14

7.1   Indemnification by the Company...........................  14
7.2   Indemnification by the Purchaser.........................  14
7.3   Notification.............................................  15

ARTICLE 8  MISCELLANEOUS                                         16

8.1   Survival of Representations and Warranties...............  16
8.2   Notices..................................................  16
8.3   Successors and Assigns; Third Party Beneficiaries........  17
8.4   Amendment and Waiver.....................................  17
8.5   Counterparts.............................................  17
8.6   Headings.................................................  17
8.7   Pronouns.................................................  17
8.8   Governing Law............................................  17
8.9   Severability.............................................  17
8.10  Entire Agreement.........................................  18
8.11  Fees.....................................................  18
8.12  Publicity................................................  18
8.13  Further Assurances.......................................  18
</TABLE>

EXHIBITS

A         Registration Agreement Amendment
B         Stockholders Agreement Amendment

SCHEDULES

3.6       Capitalization
3.7       Financial Statements

                                      ii
<PAGE>

                            STOCK PURCHASE AGREEMENT

     THIS STOCK PURCHASE AGREEMENT is dated as of May 17, 2000 (this
"Agreement"), among Synapse Group, Inc., a Delaware corporation (the "Company"),
 ---------                                                            -------
and the purchaser listed on the signature page hereto (the "Purchaser").
                                                            ---------

     WHEREAS, pursuant to the terms and conditions set forth in this Agreement,
the Company proposes to issue and sell to the Purchaser 62,500 shares of the
Company's Class B Common Stock, par value $0.001 per share ("Nonvoting Common
                                                             ----------------
Stock"), for $8.00 per share (the "Purchased Shares"); and
-----                              ----------------

     WHEREAS, each share of Nonvoting Common Stock is convertible (subject to
adjustment) into one share of Voting Common Stock.

     NOW, THEREFORE, in consideration of the mutual covenants and agreements set
forth herein and for good and valuable consideration, the receipt and adequacy
of which are hereby acknowledged, the parties hereto agree as follows:

                                   ARTICLE 1

                                  DEFINITIONS
                                  -----------

     1.1  Definitions.  As used in this Agreement, and unless the context
          -----------
requires a different meaning, the following terms have the meanings indicated:

          "Affiliate"  shall mean any Person who is an "affiliate" as defined in
           ---------
Rule 12b-2 of the General Rules and Regulations under the Exchange Act.

          "Agreement" means this Agreement as the same may be amended,
           ---------
supplemented or modified in accordance with the terms hereof.

          "Amended and Restated Shareholders Agreement" means that Amended and
           -------------------------------------------
Restated Shareholders Agreement substantially in the form attached hereto as
Exhibit A, which amends and restates that Shareholder Agreement, dated as of
---------
December 1, 1993, among the Company and the stockholders named therein.

          "Audited Financial Statements" means, with respect to a fiscal year,
           ----------------------------
the audited consolidated balance sheet of the Company as of the end of such
fiscal year and the related statements of operations, cash flows and
stockholders' equity for such fiscal year, setting forth in each case in
comparative form the figures for the previous year, all in conformity with GAAP,
in reasonable detail and accompanied by a management summary and analysis of the
operations of the Company for such fiscal year and by the opinion of a
nationally recognized independent certified public accounting firm reasonably
satisfactory to the Purchaser.

          "Board of Directors" means the Board of Directors of the Company.
           ------------------

                                      -1-
<PAGE>

          "Business Day" means any day other than a Saturday, Sunday or other
           ------------
day on which commercial banks in the State of New York are authorized or
required by law or executive order to close.

          "By-laws" means the by-laws of the Company in effect on the date
           -------
hereof, as the same may be amended from time to time.

          "Capital Lease Obligations" of any Person shall mean, as of the date
           -------------------------
of determination, the obligations of such Person to pay rent or other amounts
under any lease of (or other arrangement conveying the right to use) real or
personal property, or a combination thereof, which obligations are required to
be classified and accounted for as capital leases on a balance sheet of such
Person under GAAP and, for the purposes of this Agreement, the amount of such
obligations at any time shall be the capitalized amount thereof at such time
determined in accordance with GAAP consistently applied.

          "Certificate of Incorporation" means the certificate of incorporation
           ----------------------------
of the Company in effect on the date hereof, as the same may be amended from
time to time.

          "Claims" has the meaning set forth in Section 7.1 of this Agreement.
           ------

          "Closing" has the meaning set forth in Section 2.2 of this Agreement.
           -------

          "Closing Date" has the meaning set forth in Section 2.2 of this
           ------------
Agreement.

          "Commission" means the Securities and Exchange Commission or any
           ----------
similar agency then having jurisdiction to enforce the Securities Act and the
Exchange Act.

          "Common Stock" means the Voting Common Stock and the Nonvoting Common
           ------------
Stock.

          "Common Stock Equivalent" means any security or obligation which is by
           -----------------------
its terms convertible into or exchangeable for shares of Common Stock,
including, without limitation, any option, warrant or other subscription or
purchase right with respect to Common Stock.

          "Company" has the meaning set forth in the recitals to this Agreement.
           -------

          "Company Indemnified Party" has the meaning set forth in Section 7.2
           -------------------------
of this Agreement.

          "Condition of the Company" means the assets, business, properties,
           ------------------------
prospects, operations or financial condition of the Company.

          "Consolidated Financial Statements" has the meaning set forth in
           ---------------------------------
Section 3.7 of this Agreement.

                                      -2-
<PAGE>

          "Contractual Obligations" means as to any Person, any provision of any
           -----------------------
security issued by such Person or of any agreement, undertaking, contract,
indenture, mortgage, deed of trust or other instrument to which such Person is a
party or by which it or any of its property is bound.

          "Credit Agreement" means that Credit Agreement dated as of January 12,
           ----------------
2000 between the Company and Walker, as assigned by Walker to Arena Capital
Investment Fund, L.P. pursuant to that Assignment Agreement dated as of February
1, 2000.

          "Disclosure Schedule" has the meaning set forth in Article 3 of this
           -------------------
Agreement.

          "Exchange Act" means the Securities Exchange Act of 1934, as amended,
           ------------
and the rules and regulations of the Commission thereunder.

          "GAAP" means generally accepted accounting principles in effect from
           ----
time to time in the United States.

          "Governmental Authority" means the government of any nation, state,
           ----------------------
city, locality or other political subdivision thereof, any entity exercising
executive, legislative, judicial, regulatory or administrative functions of or
pertaining to government, and any corporation or other entity owned or
controlled, through stock or capital ownership or otherwise, by any of the
foregoing.

          "Hart-Scott-Rodino Act" means the Hart-Scott-Rodino Antitrust
           ---------------------
Improvements Act of 1976, as amended.

          "Indemnified Party" has the meaning set forth in Section 7.3 of this
           -----------------
Agreement.

          "Indemnifying Party" has the meaning set forth in Section 7.3 of this
           ------------------
Agreement.

          "Lender Warrants" means the warrants which may be issued pursuant to
           ---------------
the Credit Agreement.

          "Lien" means any mortgage, deed of trust, pledge, hypothecation,
           ----
assignment, encumbrance, lien (statutory or other) or preference, priority,
right or other security interest or preferential arrangement of any kind or
nature whatsoever (excluding preferred stock and equity related preferences),
including, without limitation, those created by, arising under or evidenced by
any conditional sale or other title retention agreement, the interest of a
lessor under a Capital Lease Obligation, or any financing lease having
substantially the same economic effect as any of the foregoing.

          "Losses" has the meaning set forth in Section 7.1 of this Agreement.
           ------

                                      -3-
<PAGE>

          "Nonvoting Common Stock" has the meaning set forth in the recitals to
           ----------------------
this Agreement.

          "Orders" has the meaning set forth in Section 3.2 of this Agreement.
           ------

          "Person" means any individual, firm, corporation, partnership, trust,
           ------
incorporated or unincorporated association, joint venture, joint stock company,
limited liability company, Governmental Authority or other entity of any kind,
and shall include any successor (by merger or otherwise) of such entity.

          "Purchased Shares" has the meaning set forth in the recitals of this
           ----------------
Agreement.

          "Purchaser" has the meaning set forth in the recitals to this
           ---------
Agreement.

          "Purchaser Indemnified Party" has the meaning set forth in Section 7.1
           ---------------------------
of this Agreement.

          "Registration Agreement Amendment" means that Amendment No. 1 to
           --------------------------------
Amended and Restated Registration Rights Agreement substantially in the form
attached hereto as Exhibit B.
                   ---------

          "Requirement of Law" means, as to any Person, any law, statute,
           ------------------
treaty, rule, regulation, right, privilege, qualification, license or franchise
or determination of an arbitrator or a court or other Governmental Authority or
stock exchange, in each case applicable or binding upon such Person or any of
its property or to which such Person or any of its property is subject or
pertaining to any or all of the transactions contemplated or referred to herein.

          "Securities Act" means the Securities Act of 1933, as amended, (or any
           --------------
successor statute thereto) and the rules and regulations of the Commission
thereunder.

          "Series A Preferred Stock" means the Company's Series A Convertible
           ------------------------
Preferred Stock, par value $0.001 per share.

          "Series B Preferred Stock" means the Company's Series B Convertible
           ------------------------
Preferred Stock, par value $0.001 per share.

          "Series C Preferred Stock" means the Company's Series C Convertible
           ------------------------
Preferred Stock, par value $0.001 per share.

          "Stockholders Agreement Amendment" means that Amendment No. 2 to and
           --------------------------------
Waiver of Amended and Restated Stockholders Agreement substantially in the form
attached hereto as Exhibit C.
                   ---------

          "Subsidiaries" means, as of the relevant date of determination, with
           ------------
respect to any Person, a corporation or other Person of which 50% or more of the
voting power of the outstanding voting equity securities or 50% or more of the
outstanding economic

                                      -4-
<PAGE>

equity interest is held, directly or indirectly, by such Person. Unless
otherwise qualified, or the context otherwise requires, all references to a
"Subsidiary" or to "Subsidiaries" in this Agreement shall refer to a Subsidiary
or Subsidiaries of the Company.

          "Tax", "Taxes" and "Tax Returns" have the meanings set forth in
           ---    -----       -----------
Section 3.9 of this Agreement.

          "Transaction Documents" means collectively, this Agreement, the
           ---------------------
Stockholders Agreement Amendment and the Registration Agreement Amendment.

          "Voting Common Stock" means the Company's Class A common stock, par
           -------------------
value $0.001 per share.

          "Walker" means Jay Walker.
           ------

          "Warrants" means those warrants to acquire Voting Common Stock issued
           --------
pursuant to the Stock and Warrant Purchase Agreement, dated as of January 12,
2000, between the Company and the Purchasers listed therein.

     1.2  Accounting Terms; Financial Statements.  All accounting terms used
          --------------------------------------
herein not expressly defined in this Agreement shall have the respective
meanings given to them in accordance with sound accounting practice.  The term
"sound accounting practice" shall mean such accounting practice as, in the
opinion of the independent certified public accountants regularly retained by
the Company, conforms at the time to GAAP applied on a consistent basis except
for changes with which such accountants concur.

                                   ARTICLE 2

                     PURCHASE AND SALE OF PURCHASED SHARES
                     -------------------------------------

     2.1  Purchase and Sale of the Purchased Shares.  Subject to the terms and
          -----------------------------------------
conditions set forth herein, the Company agrees to issue and sell to the
Purchaser, and the Purchaser agrees that he will purchase from the Company, on
the Closing Date, the Purchased Shares.

     2.2  Closing.  The closing of the sale and purchase of the Purchased Shares
          -------
(the "Closing") shall take place at the Boston offices of Hale & Dorr LLP, no
      -------
later than 10:00 a.m., local time, on the date hereof, or at such other time,
place and date that the Company and the Purchaser may agree in writing (the
"Closing Date").  On the Closing Date, the Company shall send by overnight
 ------------
courier to the Purchaser a certificate representing the Purchased Shares against
delivery by such Purchaser to the Company of the aggregate purchase price
therefor by wire transfer of immediately available funds.

                                      -5-
<PAGE>

                                   ARTICLE 3

                 REPRESENTATIONS AND WARRANTIES OF THE COMPANY
                 ----------------------------------------------

     Except as described in a disclosure schedule (the "Disclosure Schedule")
                                                        -------------------
attached hereto setting forth certain exceptions to the representations and
warranties described below, the Company represents and warrants to the Purchaser
as follows:

     3.1  Corporate Existence and Power.  The Company:  (a) is a corporation
          -----------------------------
duly organized, validly existing and in good standing under the laws of the
jurisdiction of its incorporation, (b) has all requisite corporate power and
authority to own and operate its property, to lease the property it operates as
lessee and to conduct the business in which it is currently, or is proposed to
be, engaged; (c) is duly qualified as a foreign corporation, licensed and in
good standing under the laws of each jurisdiction in which its ownership, lease
or operation of property or the conduct of its business require such
qualification, except where such failure would not result in a material adverse
effect on the Condition of the Company; and (d) has the corporate power and
authority to execute, deliver and perform its obligations under this Agreement
and each of the other Transaction Documents to which it is a party.

     3.2  Authorization; No Contravention.  The execution, delivery and
          -------------------------------
performance by the Company of this Agreement and each of the other Transaction
Documents and the transactions contemplated hereby and thereby:  (a) have been
duly authorized by all necessary corporate action of the Company; (b) do not
contravene the terms of the Certificate of Incorporation or the By-laws; (c) do
not violate, conflict with or result in any breach or contravention of, or the
creation of any Lien under, any material Contractual Obligation of the Company,
or any Requirement of Law applicable to the Company; and (d) do not violate any
judgment, injunction, writ, award, decree or order of any nature (collectively,
"Orders") of any Governmental Authority against, or binding upon, the Company.
 ------

     3.3  Governmental Authorization; Third Party Consents.  Except for the
          ------------------------------------------------
approval of the stockholders of the Company, which will be obtained prior to the
Closing, the consent of the Company's lender, Arena Capital Investment Fund,
L.P., and applicable requirements under the Hart-Scott-Rodino Act, the
Securities Act and state securities or blue sky laws, no approval, consent,
compliance, exemption, authorization or other action by, or notice to, or filing
with, any Governmental Authority or any other Person, and no lapse of a waiting
period under a Requirement of Law, is necessary or required in connection with
the execution, delivery or performance by, or enforcement against, the Company
of this Agreement and the other Transaction Documents or the transactions
contemplated hereby and thereby.

     3.4  Binding Effect.  This Agreement has been duly executed and delivered
          --------------
by the Company and, when executed, each of the other Transaction Documents will
be duly executed and delivered by the Company, and this Agreement and the other
Transaction Documents will constitute legal, valid and binding obligations of
the Company enforceable against the Company in accordance with their respective
terms, except as enforceability may be limited by applicable bankruptcy,
insolvency, reorganization,

                                      -6-
<PAGE>

fraudulent conveyance or transfer, moratorium or similar laws affecting the
enforcement of creditors' rights generally and by general principles of equity
relating to enforceability (regardless of whether considered in a proceeding at
law or in equity).

     3.5  Litigation.  There are no actions, suits, proceedings, claims,
          ----------
complaints, disputes, arbitrations or investigations pending or, to the
knowledge of the Company, threatened, at law, in equity, in arbitration or
before any Governmental Authority against the Company.  No Order has been issued
by any court or other Governmental Authority against the Company purporting to
enjoin or restrain the execution, delivery or performance of this Agreement or
any other Transaction Document.

     3.6  Capitalization. On the Closing Date, after giving effect to the
          --------------
transactions contemplated by this Agreement and assuming the consummation of the
transactions contemplated by that Stock Purchase Agreement, dated as of May 17,
2000, between the Company and NSSI Holdings Inc., a subsidiary of Time Inc., the
authorized capital stock of the Company shall consist of:  (a) 58,000,000 shares
of Voting Common Stock, of which 7,368,000 shares shall be issued and
outstanding; (b) 37,000,000 shares of Nonvoting Common Stock, of which
25,434,228 shares shall be issued and outstanding; (c) 2,600,000 shares of
Series A Preferred Stock, of which 2,591,178.24 shares shall be issued and
outstanding; (d) 5,000,000 shares of Series B Preferred Stock, all of which
shall be issued and outstanding; and (e) 3,125,000 shares of Series C Preferred
Stock, all of which shall be issued and outstanding.  Schedule 3.6 sets forth,
                                                      ------------
at and on the Closing Date and assuming the consummation of the transactions
contemplated by that Stock Purchase Agreement, dated as of May 17, 2000, between
the Company and NSSI Holdings Inc., a subsidiary of Time Inc., a true and
complete capitalization table of the Company on a fully-diluted basis.  The
Company has reserved an aggregate of 62,500 shares of Voting Common Stock for
issuance upon conversion of the Purchased Shares.  Except for the Warrants and
the Lender Warrants, and except as set forth on Schedule 3.6, there are no
                                                ------------
options, warrants, conversion privileges, subscription or purchase rights or
other rights presently outstanding to purchase or otherwise acquire (i) any
authorized but unissued, unauthorized or treasury shares of the Company's
capital stock, (ii) any Common Stock Equivalents or (iii) other securities of
the Company.  Prior to the Closing Date, the Purchased Shares shall have been
duly authorized, and when issued and sold to the Purchaser after payment
therefor in accordance herewith, will be validly issued, fully paid and
nonassessable and, assuming the accuracy of the representations and warranties
of the Purchaser set forth in Article 4, will be issued in compliance with the
registration and qualification requirements of all applicable federal and state
securities laws (or pursuant to exemptions therefrom).  The shares of Voting
Common Stock issuable upon conversion of the Purchased Shares are duly
authorized and, when issued in compliance with the provisions of the Certificate
of Incorporation, will be validly issued, fully paid and nonassessable.  The
Company has no Subsidiaries and has no commitment or obligation to acquire any
capital stock or direct or indirect equity interest in any corporation,
partnership, limited liability company, joint venture or other business entity,
other than (x) Synapse Solutions, Inc., a Delaware corporation, NewSub Magazine
Services, LLC, a Delaware limited liability company, and SynapseConnect, Inc., a
Delaware corporation, each of which is wholly-owned by the

                                      -7-
<PAGE>

Company, and (y) Gift Services, LLC, a limited liability company in which the
Company has a 49% ownership interest.

     3.7  Consolidated Financial Statements.  The Company has delivered to
          ---------------------------------
Purchaser its Audited Consolidated balance sheets as of December 31, 1999 and
1998 and the related consolidated statements of operations, stockholder deficit
and cash flows for each of the three years in the period ended December 31,
1999, a copy of which is attached as Schedule 3.7 hereto (the "Consolidated
                                     ------------              ------------
Financial Statements").  The Consolidated Financial Statements present fairly in
--------------------
all material respects the financial position of the Company and its Subsidiaries
as of December 31, 1999 and 1998 and the results of the Company's operations and
cash flows for each of the three years in the period ended December 31, 1999 in
conformity with GAAP.

     3.8  No Material Adverse Change; Ordinary Course of Business.  Since
          -------------------------------------------------------
December 31, 1999:  (a) there has not been any material adverse change, nor to
the knowledge of the Company is any such change threatened, in the Condition of
the Company; (b) the Company has not participated in any transaction or
otherwise acted outside the ordinary course of business, including, without
limitation, declaring or paying any dividend or declaring or making any
distribution to its stockholders except out of the earnings of the Company; and
(c) the Company has not increased the compensation of any of its officers or the
rate of pay of any of its employees, except as part of regular compensation
increases in the ordinary course of business.

     3.9  Taxes.  Except as described in the Disclosure Schedule:  (a) the
          -----
Company has paid or accrued all federal, state, county, local, foreign and other
taxes, including, without limitation, income taxes, estimated taxes, excise
taxes, sales taxes, use taxes, gross receipts taxes, franchise taxes, employment
and payroll related taxes, property taxes and import duties, profits taxes,
premium taxes, occupancy taxes, ad valorem taxes, severance taxes, capital levy,
production taxes, transfer taxes, withholding taxes, unemployment compensation
taxes, and other governmental charges and assessments whether or not measured in
whole or in part by net income, and including deficiencies, interest, additions
to tax or interest, and penalties with respect thereto, and including expenses
associated with disputing any proposed adjustments relating to the foregoing
(hereinafter, "Taxes" or, individually, a "Tax") which have come due, other than
               -----                       ---
Taxes being disputed, in appropriate proceedings, by the Company in good faith
for which adequate reserves have been made in accordance with GAAP; (b) the
Company has timely filed or caused to be timely filed all tax returns, reports,
forms and other such documents ("Tax Returns") that it is required to file
                                 -----------
(including all applicable extensions), and all such Tax Returns are accurate and
complete in all material respects; (c) with respect to all Tax Returns of the
Company, (i) there is no unassessed Tax deficiency proposed or, to the knowledge
of the Company, threatened against the Company, (ii) no audit is in progress, no
extension of time is in force with respect to any date on which any Tax Return
was or is to be filed and no waiver or agreement is in force for the extension
of time for the assessment or payment of any Tax, (iii) to the knowledge of the
Company, there has been no additional Tax assessment against the Company
heretofore proposed, and (iv) no waivers of the statute of limitation or
extension of time within which to assess any Tax

                                      -8-
<PAGE>

have been heretofore granted by the Company; and (d) there are no Liens for
Taxes on the assets of the Company except for Liens for Taxes not yet due.

     3.10  Disclosure.  This Agreement and the documents and certificates
           ----------
furnished to the Purchaser by the Company, taken as a whole, do not contain any
untrue statement of a material fact or to the Company's knowledge omit to state
a material fact necessary in order to make the statements contained herein or
therein, in the light of the circumstances under which they were made, not
misleading.

     3.11  Private Offering.  No form of general solicitation or general
           ----------------
advertising was used by the Company or its representatives in connection with
the sale of the Purchased Shares.  Assuming the accuracy of the representations
and warranties of the Purchaser set forth in Article 4, no registration of the
Purchased Shares, pursuant to the provisions of the Securities Act or any state
securities or "blue sky" laws, will be required by the sale of the Purchased
Shares.

     3.12  No Default or Breach; Contractual Obligations.  All of the
           ---------------------------------------------
Contractual Obligations which are material to the Condition of the Company are
valid, subsisting, in full force and effect and binding upon the Company, except
as such enforceability may be limited by bankruptcy, moratorium or similar laws
affecting or relating to creditors' rights generally, and general principles of
equity, and the Company has paid in full or accrued all amounts due thereunder
and has satisfied in full or provided for all of its liabilities and obligations
thereunder in all material respects.  To the knowledge of the Company, no other
party to any such Contractual Obligation is in default thereunder, nor does any
condition exist that with notice or lapse of time or both would constitute a
default by such other party thereunder.  The Company has not received notice of,
and is not in default under or with respect to, any Contractual Obligation of
the Company in any respect, which, individually or together with all such
defaults, could have a material adverse effect on (a) the Condition of the
Company or (b) the ability of the Company to perform its obligations under this
Agreement or the other Transaction Documents.

     3.13  Broker's, Finder's or Similar Fees.  There are no brokerage
           ----------------------------------
commissions, finder's fees or similar fees or commissions payable by the Company
in connection with the transactions contemplated hereby based on any agreement,
arrangement or understanding with the Company or any action taken by the
Company.

                                   ARTICLE 4

                REPRESENTATIONS AND WARRANTIES OF THE PURCHASER
                -----------------------------------------------

     The Purchaser hereby represents and warrants to the Company, as of the date
hereof and as of the Closing Date, as follows:

     4.1  Existence and Power.  It is, if applicable, a partnership or other
          -------------------
entity duly organized, validly existing and in good standing under the laws of
the jurisdiction of its formation and has all requisite power and authority, or
requisite legal capacity (in the case

                                      -9-
<PAGE>

of an individual), as the case may be, to execute, deliver and perform its
obligations under this Agreement and each of the other Transaction Documents to
which it is a party.

     4.2  Authorization; No Contravention.  The execution, delivery and
          -------------------------------
performance by it of this Agreement and each of the other Transaction Documents
to which it is a party and the transactions contemplated hereby and thereby:
(a) have been duly authorized by all necessary partnership or other action, if
applicable; (b) do not contravene the terms of its organizational documents, or
any amendment thereof, if applicable; (c) do not violate, conflict with or
result in any breach or contravention of or the creation of any Lien under, any
Contractual Obligation of it, or any Requirement of Law applicable to it; and
(d) do not violate any Orders of any Governmental Authority against, or binding
upon, it.

     4.3  Governmental Authorization; Third Party Consents. Except for
          ------------------------------------------------
applicable requirements under the Hart-Scott-Rodino Act, the Securities Act and
state securities or blue sky laws, no approval, consent, compliance, exemption,
authorization, or other action by, or notice to, or filing with, any
Governmental Authority or any other Person, and no lapse of a waiting period
under any Requirement of Law is necessary or required in connection with the
execution, delivery or performance by, or enforcement against, it of this
Agreement and each of the other Transaction Documents or the transactions
contemplated hereby and thereby.

     4.4  Binding Effect.  This Agreement and each of the other Transaction
          --------------
Documents have been duly executed and delivered by it, and constitutes its
legal, valid and binding obligations, enforceable against it in accordance with
their terms, except as enforceability may be limited by applicable bankruptcy,
insolvency, reorganization, fraudulent conveyance or transfer, moratorium or
similar laws affecting the enforcement of creditors' rights generally or by
equitable principles relating to enforceability (regardless of whether
considered in a proceeding at law or in equity).

     4.5  Purchase for Own Account.  The Purchased Shares to be acquired by it
          ------------------------
pursuant to this Agreement are being or will be acquired for investment for its
own account and with no intention of distributing or reselling, or granting any
participation in, such Purchased Shares or any part thereof in any transaction
that would be in violation of the securities laws of the United States of
America, or any state, without prejudice, however, to the rights of it at all
times to sell or otherwise dispose of all or any part of such Purchased Shares
under an effective registration statement under the Securities Act, or under an
exemption from such registration available under such laws, and subject,
nevertheless, to the disposition of it's property being at all times within its
control.  If it should in the future decide to dispose of any of such Purchased
Shares, it understands and agrees that it may do so only in compliance with the
Securities Act and applicable state securities laws, as then in effect.  It
agrees to the imprinting, so long as required by law, of legends on certificates
representing all of its Purchased Shares as required by any applicable state
securities laws and to the following effect (and acknowledges that the Company
will make a notation on its transfer books to such effect):

                                      -10-
<PAGE>

     THE SECURITIES REPRESENTED BY THIS CERTIFICATE HAVE NOT BEEN
     REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE
     "ACT"), OR THE SECURITIES LAWS OF ANY JURISDICTION OF THE UNITED
     STATES. THE SECURITIES MAY NOT BE TRANSFERRED EXCEPT PURSUANT TO
     AN EFFECTIVE REGISTRATION STATEMENT UNDER SUCH ACT AND UNDER THE
     APPLICABLE STATE SECURITIES LAWS OR PURSUANT TO AN OPINION OF
     COUNSEL REASONABLY SATISFACTORY TO SYNAPSE GROUP, INC. (THE
     "COMPANY"), IF REQUESTED BY THE COMPANY, THAT THERE IS AN
     APPLICABLE EXEMPTION FROM THE REGISTRATION REQUIREMENTS OF SUCH
     ACT AND SUCH LAWS.

     THE SALE, ASSIGNMENT, HYPOTHECATION, PLEDGE, ENCUMBRANCE OR OTHER
     DISPOSITION (EACH A "TRANSFER") AND VOTING OF ANY OF THE
     SECURITIES REPRESENTED BY THIS CERTIFICATE ARE RESTRICTED BY THE
     TERMS OF AN AMENDED AND RESTATED STOCKHOLDERS AGREEMENT AMONG THE
     COMPANY AND THE STOCKHOLDERS NAMED THEREIN. THE COMPANY WILL NOT
     REGISTER THE TRANSFER OF SUCH SECURITIES ON THE BOOKS OF THE
     COMPANY UNLESS AND UNTIL THE TRANSFER HAS BEEN MADE IN COMPLIANCE
     WITH THE TERMS OF SUCH AGREEMENT. THE COMPANY WILL MAIL A COPY OF
     THE AGREEMENT, TOGETHER WITH A COPY OF THE EXPRESS TERMS OF THE
     SECURITIES AND THE OTHER CLASS OR CLASSES AND SERIES OF SHARES,
     IF ANY, WHICH THE COMPANY IS AUTHORIZED TO ISSUE, TO THE RECORD
     HOLDER OF THIS CERTIFICATE, WITHOUT CHARGE, WITHIN FIVE DAYS
     AFTER RECEIPT OF A WRITTEN REQUEST THEREFOR.

     4.6  Investment Experience; Information.  It is an "Accredited Investor" as
          ----------------------------------
defined in Rule 501(a) under the Securities Act.  It has received a copy of the
closing binder of documents entered into in connection with the Company's sale
of Series B Preferred Stock and execution of the Credit Agreement on January 12,
2000.

     4.7  Broker's, Finder's or Similar Fees.  There are no brokerage
          ----------------------------------
commissions, finder's fees or similar fees or commissions payable by it, in
connection with the transactions contemplated hereby based on any agreement,
arrangement or understanding with it or any action taken by it.

                                      -11-
<PAGE>

                                   ARTICLE 5

                 CONDITIONS TO THE OBLIGATION OF THE PURCHASER
                                    TO CLOSE
                                    --------

     The obligation of the Purchaser to purchase the Purchased Shares, to pay
the purchase price therefor at the Closing and to perform its other obligations
hereunder shall be subject to the satisfaction as determined by, or waiver by,
such Purchaser of the following conditions on the Closing Date.

     5.1  Secretary's Certificate.  The Purchaser shall have received a
          -----------------------
certificate from the Company, in form and substance reasonably satisfactory to
the Purchaser, dated the Closing Date and signed by the Secretary or an
Assistant Secretary of the Company, certifying that the attached copies of the
Certificate of Incorporation, the By-laws and resolutions of the Board of
Directors approving this Agreement and each of the other Transaction Documents
and the transactions contemplated hereby and thereby, are all true, complete and
correct and remain unamended and in full force and effect.

     5.2  Stockholders Agreement Amendment.  The Company and the stockholders
          --------------------------------
named therein shall have duly executed and delivered the Stockholders Agreement
Amendment.

     5.3  Registration Agreement Amendment. The Company and the stockholders
          --------------------------------
named therein shall have duly executed and delivered the Registration Agreement
Amendment.

     5.4  Amended and Restated Shareholders Agreement. Each of the stockholders
          -------------------------------------------
party to the Amended and Restated Shareholders Agreement shall have duly
executed and delivered the Amended and Restated Shareholders Agreement.

     5.5  Purchased Shares.  The Company shall have sent by overnight courier to
          ----------------
the Purchaser certificates in definitive form representing the Purchased Shares.

     5.6  Consents and Approvals.  All consents, exemptions, authorizations, or
          ----------------------
other actions by, or notices to, or filings with, Governmental Authorities and
other Persons in respect of all Requirements of Law and with respect to all
Contractual Obligations which are necessary or required in connection with the
execution, delivery or performance by, or enforcement against, the Company and
the Purchaser of this Agreement and each of the other Transaction Documents
shall have been obtained and be in full force and effect, including without
limitation, all applicable waiting periods (and any extensions thereof) under
the Hart-Scott-Rodino Act shall have expired or otherwise been terminated, and
the Purchaser shall have been furnished with appropriate evidence thereof and
all applicable waiting periods shall have expired without any action being taken
or threatened which would have a material adverse effect on the Condition of the
Company.

                                      -12-
<PAGE>

     5.7  Receipt of Consolidated Financial Statements.  The Company shall have
          --------------------------------------------
delivered the Consolidated Financial Statements to the Purchaser, in form and
substance reasonably satisfactory to the Purchaser.

                                   ARTICLE 6

                  CONDITIONS TO THE OBLIGATION OF THE COMPANY
                                   TO CLOSE
                                   --------

     The obligation of the Company to sell the Purchased Shares and to perform
its obligations hereunder shall be subject to the satisfaction as determined by,
or waiver by, the Company of the following conditions on or before the Closing
Date:

     6.1  Payment by the Purchaser.  The Purchaser shall have purchased and paid
          ------------------------
for the Purchased Shares.

     6.2  Stockholders Agreement Amendment.  The Purchaser shall have duly
          --------------------------------
executed and delivered the Stockholders Agreement Amendment and an
Acknowledgement and Agreement attached as Exhibit C-2 to that Amended and
Restated Stockholders Agreement dated as of January 12, 2000.

     6.3  Registration Agreement Amendment.  The Purchaser shall have duly
          --------------------------------
executed and delivered the Registration Agreement Amendment.

     6.4  Amended and Restated Shareholders Agreement. Each of the stockholders
          -------------------------------------------
party to the Amended and Restated Shareholders Agreement shall have duly
executed and delivered the Amended and Restated Shareholders Agreement.

     6.5  Consents and Approvals.  All consents, exemptions, authorizations, or
          ----------------------
other actions by, or notices to, or filings with, Governmental Authorities and
other Persons in respect of all Requirements of Law and with respect to all
Contractual Obligations which are necessary or required in connection with the
execution, delivery or performance by, or enforcement against, the Company and
the Purchaser of this Agreement and each of the other Transaction Documents
shall have been obtained and be in full force and effect, including without
limitation, all applicable waiting periods (and any extensions thereof) under
the Hart-Scott-Rodino Act shall have expired or otherwise been terminated, and
the Company shall have been furnished with appropriate evidence thereof and all
applicable waiting periods shall have expired without any action being taken or
threatened which would have a material adverse effect on the Condition of the
Company.

                                      -13-
<PAGE>

                                   ARTICLE 7

                                INDEMNIFICATION
                                ---------------

     7.1  Indemnification by the Company.  Except as otherwise provided in this
          ------------------------------
Article 7, the Company agrees to indemnify, defend and hold harmless the
Purchaser and his Affiliates and its respective officers, directors, agents,
employees, subsidiaries, partners, members and controlling persons (each, a
"Purchaser Indemnified Party") to the fullest extent permitted by law from and
 ---------------------------
against any and all losses and any and all actions, proceedings, claims,
complaints, disputes, arbitrations or investigations or written threats thereof
(collectively, "Claims") (including any Claim by a third party), damages,
                ------
expenses (including reasonable fees, disbursements and other charges of counsel
incurred by the Purchaser Indemnified Party in any action between the Company
and the Purchaser Indemnified Party or between the Purchaser Indemnified Party
and any third party or otherwise) or other liabilities (collectively, "Losses")
                                                                       ------
resulting from, arising out of or relating to the breach by the Company of any
representation or warranty or covenant set forth in Article 3, or relating to
the breach of any other agreement by the Company in this Agreement or the other
Transaction Documents; provided, that the Company shall not be liable under this
                       --------
Section 7.1 to a Purchaser Indemnified Party to the extent that it is finally
judicially determined that such Losses resulted primarily from the material
breach by such Purchaser Indemnified Party of any representation, warranty,
covenant or other agreement of such Purchaser Indemnified Party contained in
this Agreement or other Transaction Documents; and provided, further, that if
                                                   --------  -------
and to the extent that such indemnification is unenforceable for any reason, the
Company shall make the maximum contribution to the payment and satisfaction of
such Losses which shall be permissible under applicable laws.  Notwithstanding
anything to the contrary contained herein, the amount of any payment by the
Company to any Purchaser Indemnified Party herewith in respect of any Loss shall
not exceed the aggregate purchase price paid by the Purchaser for the Purchased
Shares.  In connection with the obligation of the Company to indemnify for
expenses as set forth above, the Company shall, upon presentation of appropriate
invoices containing reasonable detail, reimburse each Purchaser Indemnified
Party for all such expenses (including reasonable fees, disbursements and other
charges of counsel incurred by the Purchaser Indemnified Party) only (a) after
the final resolution or disposition of such Claim and (b) if such Purchaser
Indemnified Party prevails in such Claim; provided, however, that if a Purchaser
                                          -----------------
Indemnified Party is reimbursed hereunder for any expenses, such reimbursement
of expenses shall be refunded to the extent it is finally judicially determined
that the Losses in question resulted primarily from the willful misconduct or
gross negligence of such Purchaser Indemnified Party.

     7.2  Indemnification by the Purchaser.  Except as otherwise provided in
          --------------------------------
this Article 7, the Purchaser agrees to indemnify, defend and hold harmless the
Company and its officers, directors, shareholders, agents, employees,
subsidiaries, partners, members and controlling persons (each, a "Company
                                                                  -------
Indemnified Party") to the fullest extent permitted by law from and against any
-----------------
and all Losses resulting from, arising out of or relating to any breach of the
representation or warranty or covenant set forth in Article 4; provided, that
                                                               --------
the Purchaser shall not be liable under this Section 7.2 to a Company
Indemnified Party to the extent that it is finally judicially determined that
such Losses

                                      -14-
<PAGE>

resulted primarily from the material breach by such Company Indemnified Party of
any representation, warranty, covenant or other agreement of such Company
Indemnified Party contained in this Agreement or the other Transaction
Documents; and provided, further, that if and to the extent that such
               --------  -------
indemnification is unenforceable for any reason, the Purchaser shall make the
maximum contribution to the payment and satisfaction of such Losses which shall
be permissible under applicable laws. The aggregate amount of indemnification
payments payable to the Company Indemnified Party shall not exceed the aggregate
purchase price paid by the Purchaser for the Purchased Shares.

     7.3  Notification.  Each Purchaser Indemnified Party or Company Indemnified
          ------------
Party, as the case may be (for purposes of this Section 7.3, an "Indemnified
                                                                 -----------
Party"), under this Article 7 shall, promptly after the receipt of notice of the
-----
commencement of any action, investigation, claim or other proceeding against
such Indemnified Party in respect of which indemnity may be sought from the
Company or the Purchaser, as the case may be (an "Indemnifying Party"), under
                                                  ------------------
this Article 7, notify the Indemnifying Party in writing of the commencement
thereof.  The omission of any Indemnified Party to so notify the Indemnifying
Party of any such action shall not relieve the Indemnifying Party from any
liability which it may have to such Indemnified Party (a) other than pursuant to
this Article 7 or (b) under this Article 7 unless, and only to the extent that,
such omission results in the Indemnifying Party's forfeiture of substantive
rights or defenses.  In case any such action, claim or other proceeding shall be
brought against any Indemnified Party, and it shall notify the Indemnifying
Party of the commencement thereof, the Indemnifying Party shall be entitled to
assume the defense thereof at its own expense, with counsel satisfactory to such
Indemnified Party in its reasonable judgment; provided, however, that any
                                              -----------------
Indemnified Party may, at its own expense, retain separate counsel to
participate in such defense at its own expense.  Notwithstanding the foregoing,
in any action, claim or proceeding in which both the Indemnifying Party, on the
one hand, and an Indemnified Party, on the other hand, are, or are reasonably
likely to become, a party, such Indemnified Party shall have the right to employ
separate counsel at the expense of the Indemnifying Party and to control its own
defense of such action, claim or proceeding if, in the reasonable opinion of
counsel to such Indemnified Party, a conflict or potential conflict exists
between the Indemnifying Party, on the one hand, and such Indemnified Party, on
the other hand, that would make such separate representation advisable;
provided, however, that the Indemnifying Party shall not be liable for the fees
-----------------
and expenses of more than one counsel to all Indemnified Parties.  The
Indemnifying Party agrees that it will not, without the prior written consent of
the Indemnified Party, settle, compromise or consent to the entry of any
judgment in any pending or threatened claim, action or proceeding relating to
the matters contemplated hereby (if any Indemnified Party is a party thereto or
has been actually threatened to be made a party thereto) unless such settlement,
compromise or consent includes an unconditional release of each Indemnified
Party from all liability arising or that may arise out of such claim, action or
proceeding.  The Indemnifying Party shall not be liable for any settlement of
any claim, action or proceeding effected against an Indemnified Party without
the Indemnifying Party's written consent, which consent shall not be
unreasonably withheld.  The rights accorded to an Indemnified Party hereunder
shall be in addition to any rights that any Indemnified Party may have at common
law, by separate agreement or otherwise; provided, however, that notwithstanding
                                         -----------------
the foregoing or anything to the contrary contained in this

                                      -15-
<PAGE>

Agreement, nothing in this Article 7 should restrict or limit any rights that
any Indemnified Party may have to seek equitable relief.

                                   ARTICLE 8

                                 MISCELLANEOUS
                                 -------------

     8.1  Survival of Representations and Warranties.  Except for the
          ------------------------------------------
representations and warranties set forth in Sections 3.1, 3.2, 3.4, 3.6, 3.7,
3.9, 3.13, 4.1, 4.2, 4.4, 4.5, 4.6 and 4.7 herein, which shall survive the
execution and delivery of this Agreement, any investigation by or on behalf of
the Company or the Purchaser, or acceptance of the Purchased Shares or
termination of this Agreement, all of the representations and warranties made
herein shall survive the execution and delivery of this Agreement, any
investigation by or on behalf of the Company or the Purchaser, or acceptance of
the Purchased Shares or termination of this Agreement until forty-five (45) days
after receipt by Purchaser of the Audited Financial Statements of the Company
for the fiscal year ending December 31, 2000.

     8.2  Notices.  All notices, demands and other communications provided for
          -------
or permitted hereunder shall be made in writing and shall be by registered or
certified first-class mail, return receipt requested, telecopier, courier
service or personal delivery to the addresses set forth below:

               (a)  if to the Company:

                    Synapse Group, Inc.
                    4 High Ridge Park
                    Stamford, CT 06905-1325
                    Telecopy:  (203) 595-8254
                    Attention: Mr. Michael Loeb

                    with a copy to:

                    Hale and Dorr LLP
                    60 State Street
                    Boston, MA 02109
                    Telecopy:  (617) 526-5000
                    Attention: John H. Chory, Esq.

               (b)  if to the Purchaser, to the addresses indicated on the
signature page hereto.

All such notices and communications shall be deemed to have been duly given when
delivered by hand, if personally delivered; when delivered by courier, if
delivered by commercial courier service; five (5) Business Days after being
deposited in the mail, postage prepaid, if mailed; and when receipt is
mechanically acknowledged, if properly telecopied.

                                      -16-
<PAGE>

     8.3  Successors and Assigns; Third Party Beneficiaries.  This Agreement
          -------------------------------------------------
shall inure to the benefit of and be binding upon the successors and permitted
assigns of the parties hereto.  Subject to applicable securities laws, the
Purchaser may assign any of its rights under this Agreement to any of its
Affiliates upon notice to the Company, provided such Affiliate is not directly
or indirectly engaged in a business competitive with the business of the
Company.  The Company may not assign any of its rights under this Agreement
without the written consent of the Purchaser.  Except as provided in Article 7,
no Person other than the parties hereto and their successors and permitted
assigns is intended to be a beneficiary of this Agreement.

     8.4  Amendment and Waiver.
          --------------------

          (a) No failure or delay on the part of the Company or the Purchaser in
exercising any right, power or remedy hereunder shall operate as a waiver
thereof, nor shall any single or partial exercise of any such right, power or
remedy preclude any other or further exercise thereof or the exercise of any
other right, power or remedy.  The remedies provided for herein are cumulative
and are not exclusive of any remedies that may be available to the Company or
the Purchaser at law, in equity or otherwise.

          (b) Any amendment, supplement or modification of or to any provision
of this Agreement, any waiver of any provision of this Agreement, and any
consent to any departure by the Company or the Purchaser from the terms of any
provision of this Agreement, shall be effective only if it is made or given in
writing and signed by the Company and the Purchaser.

     8.5  Counterparts.  This Agreement may be executed in any number of
          ------------
counterparts and by the parties hereto in separate counterparts, each of which
when so executed shall be deemed to be an original and all of which taken
together shall constitute one and the same agreement.

     8.6  Headings.  The headings in this Agreement are for convenience of
          --------
reference only and shall not limit or otherwise affect the meaning hereof.

     8.7  Pronouns.  All pronouns and any variations thereof refer to the
          --------
masculine, feminine or neuter, singular or plural, as the context may require.

     8.8  GOVERNING LAW.  THIS AGREEMENT SHALL BE GOVERNED BY AND CONSTRUED IN
          -------------
ACCORDANCE WITH THE LAWS OF THE STATE OF NEW YORK, WITHOUT REGARD TO THE
PRINCIPLES OF CONFLICTS OF LAW OF ANY JURISDICTION.

     8.9  Severability.  If any one or more of the provisions contained herein,
          ------------
or the application thereof in any circumstance, is held invalid, illegal or
unenforceable in any respect for any reason, the validity, legality and
enforceability of any such provision in every other respect and of the remaining
provisions hereof shall not be in any way impaired, unless the provisions held
invalid, illegal or unenforceable shall substantially impair the benefits of the
remaining provisions hereof.

                                      -17-
<PAGE>

     8.10  Entire Agreement.  This Agreement, together with the exhibits and
           ----------------
schedules hereto and the other Transaction Documents, is intended by the parties
as a final expression of their agreement and intended to be a complete and
exclusive statement of the agreement and understanding of the parties hereto in
respect of the subject matter contained herein and therein.  There are no
restrictions, promises, warranties or undertakings, other than those set forth
or referred to herein or therein.  This Agreement, together with the exhibits
hereto, and the other Transaction Documents supersede all prior agreements and
understandings between the parties with respect to such subject matter.

     8.11  Fees.  Each of the parties hereto shall bear its own costs and
           ----
expenses incurred in connection with the transactions contemplated by the
Transaction Documents, including, without limitation, its fees, disbursements
and other charges of counsel.

     8.12  Publicity.  Except as may be required by any applicable Requirement
           ---------
of Law, none of the parties hereto shall issue a publicity release or public
announcement or otherwise make any public disclosure concerning this Agreement
or the transactions contemplated hereby, without prior approval by the other
parties hereto (which approval shall not be unreasonably withheld); provided,
                                                                    --------
however, that nothing in this Agreement shall restrict the Purchaser from
-------
disclosing information:  (a) that is already publicly available; (b) to the
prospective transferee in connection with any contemplated transfer of any of
the Purchased Shares; and (c) to its attorneys, accountants, consultants and
other advisors to the extent necessary to obtain their services in connection
with that Purchaser's investment in the Company.  If any announcement is
required by any applicable Requirement of Law to be made by any party hereto,
prior to making such announcement such party will deliver a draft of such
announcement to the other parties and shall give the other parties an
opportunity to comment thereon.

     8.13  Further Assurances.  Each of the parties shall execute such documents
           ------------------
and perform such further acts (including, without limitation, obtaining any
consents, exemptions, authorizations or other actions by, or giving any notices
to, or making any filings with, any Governmental Authority or any other Person,
and otherwise fulfilling, or causing the fulfillment of, the conditions to
Closing set forth in Articles 5 and 6) as may be reasonably required or
desirable to carry out or to perform the provisions of this Agreement and to
consummate and make effective as promptly as possible the transactions
contemplated by this Agreement.

              [Remainder of this page intentionally left blank.]

                                      -18-
<PAGE>

     IN WITNESS WHEREOF, the parties hereto have caused this Agreement to be
executed and delivered by their respective officers hereunto duly authorized on
the date first above written.

                                        the "Company"

                                        SYNAPSE GROUP, INC.

                                        By: /s/ Michael R. Loeb
                                           --------------------
                                           Name: Michael Loeb
                                           Title: President

                                        the "Purchaser"

                                        /s/ Richard Braddock
                                        --------------------
                                        RICHARD BRADDOCK

                                        Address:

                                        800 Connecticut Avenue
                                        Norwalk, CT  06854
                                        Attention:  ____________________
                                        Telecopier: (203) 299-8912

                                      -19-<PAGE>

                                                                   Exhibit 10.15

                           STOCK PURCHASE AGREEMENT

                                    between

                             SYNAPSE GROUP, INC.,

                                      and

                              NSSI HOLDINGS INC.

                        ______________________________

                           Dated as of May 17, 2000

                        ______________________________
<PAGE>

                               TABLE OF CONTENTS
                               -----------------

<TABLE>
<CAPTION>
                                                                      Page
                                                                      ----
<S>        <C>                                                        <C>
ARTICLE 1  DEFINITIONS...............................................    1
  1.1   Definitions..................................................    1
  1.2   Accounting Terms.............................................    5
ARTICLE 2  PURCHASE AND SALE OF SERIES C PREFERRED STOCK.............    5
  2.1   Purchase and Sale of Series C Preferred Stock................    5
  2.2   Restated Charter.............................................    6
  2.3   Closing......................................................    6
ARTICLE 3  REPRESENTATIONS AND WARRANTIES OF THE COMPANY.............    6
  3.1   Corporate Existence and Power................................    6
  3.2   Authorization, No Contravention..............................    6
  3.3   Governmental Authorization; Third Party Consents.............    6
  3.4   Binding Effect...............................................    7
  3.5   Litigation...................................................    7
  3.6   Capitalization...............................................    7
  3.7   Consolidated Financial Statements............................    8
  3.8   No Material Adverse Change; Ordinary Course of Business......    8
  3.9   Taxes........................................................    9
  3.10  Disclosure...................................................    9
  3.11  Private Offering.............................................    9
  3.12  No Default or Breach; Contractual Obligations................    9
  3.13  Agreements...................................................   10
  3.14  Labor Agreements and Actions.................................   11
  3.15  Properties...................................................   11
  3.16  Intellectual Property........................................   12
  3.17  Interested Party Transactions................................   12
  3.18  Registration Statement.......................................   13
  3.19  Prior Subscription Documents.................................   13
  3.20  Broker's, Finder's or Similar Fees...........................   13
ARTICLE 4  REPRESENTATIONS AND WARRANTIES OF PURCHASER...............   13
  4.1   Existence and Power..........................................   13
  4.2   Authorization; No Contravention..............................   13
  4.3   Governmental Authorization; Third Party Consents.............   14
  4.4   Binding Effect...............................................   14
  4.5   Purchase for Own Account.....................................   14
  4.6   Investment Experience........................................   15
  4.7   Broker's, Finder's or Similar Fees...........................   15
ARTICLE 5  CONDITIONS TO THE OBLIGATION OF PURCHASER TO CLOSE........   15
  5.1   Representations; Secretary's Certificate.....................   15
  5.2   Stockholders Agreement.......................................   15
  5.3   Registration Rights Agreement................................   16
  5.4   Filing of Restated Charter...................................   16
  5.5   Purchased Shares.............................................   16
</TABLE>

                                       i
<PAGE>

<TABLE>
<CAPTION>
                                                                      Page
                                                                      ----
<S>        <C>                                                        <C>
  5.6   Consents and Approvals.......................................   16
  5.7   Receipt of Consolidated Financial Statements.................   16
  5.8   Walker Sale Agreement........................................   16
  5.9   Amended and Restated Minor Shareholder Agreement.............   16
  5.10  Director Approvals...........................................   16
  5.11  Letter Agreement.............................................   16
ARTICLE 6  CONDITIONS TO THE OBLIGATION OF THE COMPANY TO CLOSE......   17
  6.1   Payment by Purchaser.........................................   17
  6.2   Consents and Approvals.......................................   17
  6.3   Walker Sale Agreement and Indemnification Agreement..........   18
  6.4   Time Guarantee...............................................   18
  6.5   Director Approvals...........................................   18
  6.6   Letter Agreement.............................................   18
ARTICLE 7  INDEMNIFICATION...........................................   18
  7.1   Indemnification by the Company...............................   18
  7.2   Indemnification by Purchaser.................................   19
  7.3   Notification.................................................   19
ARTICLE 8  BOARD REPRESENTATION; OBSERVER STATUS.....................   20
ARTICLE 9  MISCELLANEOUS.............................................   21
  9.1   Survival of Representations and Warranties...................   21
  9.2   Notices......................................................   21
  9.3   Successors and Assigns; Third Party Beneficiaries............   22
  9.4   Amendment and Waiver.........................................   22
  9.5   Counterparts.................................................   23
  9.6   Headings.....................................................   23
  9.7   Pronouns.....................................................   23
  9.8   GOVERNING LAW; JURISDICTION..................................   23
  9.9   Severability.................................................   23
  9.10  Entire Agreement.............................................   23
  9.11  Fees.........................................................   24
  9.12  Publicity....................................................   24
  9.13  Further Assurances...........................................   24
</TABLE>

EXHIBITS

A         Amended and Restated Minor Shareholder Agreement
B         Second Amended and Restated Registration Rights Agreement
C         Restated Certificate of Incorporation
D         Second Amended and Restated Stockholders Agreement
E         Guarantee
F         Letter Agreement

                                       ii
<PAGE>

SCHEDULES

3.6       Capitalization
3.7       Financial Statements

                                      iii
<PAGE>

                           STOCK PURCHASE AGREEMENT

     THIS STOCK PURCHASE AGREEMENT is dated as of May 17, 2000 (this

"Agreement"), between Synapse Group, Inc., a Delaware corporation (the
 ---------
"Company"), and NSSI Holdings Inc., a Delaware corporation ("Purchaser").
 -------                                                     ---------

     WHEREAS, pursuant to the terms and conditions set forth in this Agreement,
the Company proposes to issue and sell to Purchaser 3,125,000 shares (the

"Purchased Shares") of the Company's Series C Convertible Preferred Stock, par
 ----------------
value $0.001 per share (the "Series C Preferred Stock"), for an aggregate
                             ------------------------
purchase price of $25,000,000 (the "Purchase Price"); and
                                    --------------

     WHEREAS, each share of Series C Preferred Stock is convertible (subject to
adjustment) into one share of Voting Common Stock (as defined below).

     NOW, THEREFORE, in consideration of the mutual covenants and agreements set
forth herein and for good and valuable consideration, the receipt and adequacy
of which are hereby acknowledged, the parties hereto agree as follows:

                                   ARTICLE 1

                                  DEFINITIONS
                                  -----------

     1.1  Definitions.  As used in this Agreement, and unless the context
          -----------
requires a different meaning, the following terms have the meanings indicated:

          "Affiliate"  shall mean any Person who is an "affiliate" as defined in
           ---------
Rule 12b-2 of the General Rules and Regulations under the Exchange Act.

          "Agreement" means this Agreement as the same may be amended,
           ---------
supplemented or modified in accordance with the terms hereof.

          "Amended and Restated Minor Shareholder Agreement" means that Amended
           ------------------------------------------------
and Restated Shareholder Agreement amending and restating in its entirety the
Shareholder Agreement, dated December 1, 1993, among the Company and the
stockholders listed on the signature page thereto, substantially in the form
attached hereto as Exhibit A.
                   ---------

          "Audited Financial Statements" means, with respect to a fiscal year,
           ----------------------------
the audited consolidated balance sheet of the Company as of the end of such
fiscal year and the related statements of operations, stockholder deficit and
cash flows for such fiscal year, setting forth in each case in comparative form
the figures for the previous year, all in conformity with GAAP, in reasonable
detail and accompanied by a management summary and analysis of the operations of
the Company for such fiscal year and by the opinion of a nationally recognized
independent certified public accounting firm reasonably satisfactory to
Purchaser.

          "Benefit Plans" has the meaning set forth in Section 3.13 of this
           -------------
Agreement.

          "Board of Directors" means the Board of Directors of the Company.
           ------------------

                                       1
<PAGE>

          "Business Day" means any day other than a Saturday, Sunday or other
           ------------
day on which commercial banks in the State of New York are authorized or
required by law or executive order to close.

          "By-laws" means the by-laws of the Company in effect on the date
           -------
hereof, as the same may be amended from time to time.

          "Capital Lease Obligations" of any Person shall mean, as of the date
           -------------------------
of determination, the obligations of such Person to pay rent or other amounts
under any lease of (or other arrangement conveying the right to use) real or
personal property, or a combination thereof, which obligations are required to
be classified and accounted for as capital leases on a balance sheet of such
Person under GAAP and, for the purposes of this Agreement, the amount of such
obligations at any time shall be the capitalized amount thereof at such time
determined in accordance with GAAP consistently applied.

          "Claims" has the meaning set forth in Section 7.1 of this Agreement.
           ------

          "Closing" has the meaning set forth in Section 2.3 of this Agreement.
           -------

          "Closing Date" has the meaning set forth in Section 2.3 of this
           ------------
Agreement.

          "Commission" means the Securities and Exchange Commission or any
           ----------
similar agency then having jurisdiction to enforce the Securities Act and the
Exchange Act.

          "Common Stock" means the Voting Common Stock and the Nonvoting Common
           ------------
Stock.

          "Common Stock Equivalent" means any security or obligation which is by
           -----------------------
its terms convertible into or exchangeable for shares of Common Stock,
including, without limitation, any option, warrant or other subscription or
purchase right with respect to Common Stock.

          "Company" has the meaning set forth in the recitals to this Agreement.
           -------

          "Company Indemnified Party" has the meaning set forth in Section 7.2
           -------------------------
of this Agreement.

          "Condition of the Company" means the assets, business, properties,
           ------------------------
prospects, operations or financial condition of the Company and its Subsidiaries
in the aggregate.

          "Consolidated Financial Statements" has the meaning set forth in
           ---------------------------------
Section 3.7 of this Agreement.

          "Contractual Obligations" means as to any Person, any provision of any
           -----------------------
security issued by such Person or of any agreement, undertaking, contract,
indenture, mortgage, deed of trust or other instrument to which such Person is a
party or by which it or any of its property is bound.

                                       2
<PAGE>

          "Credit Agreement" means that Credit Agreement dated as of January 12,
           ----------------
2000 between the Company and Walker, as assigned by Walker to Arena Capital
Investment Fund, L.P. pursuant to that Assignment Agreement dated as of February
1, 2000.

          "Disclosure Schedule" has the meaning set forth in Article 3 of this
           -------------------
Agreement.

          "ERISA" has the meaning set forth in Section 3.13 of this Agreement.
           -----

          "Exchange Act" means the Securities Exchange Act of 1934, as amended
           ------------
(or any successor statute thereto), and the rules and regulations of the
Commission thereunder.

          "Form S-1" has the meaning set forth in Section 3.18 of this
           --------
Agreement.

          "GAAP" means generally accepted accounting principles in effect from
           ----
time to time in the United States.

          "Governmental Authority" means the government of any nation, state,
           ----------------------
city, locality or other political subdivision thereof, any entity exercising
executive, legislative, judicial, regulatory or administrative functions of or
pertaining to government, and any corporation or other entity owned or
controlled, through stock or capital ownership or otherwise, by any of the
foregoing.

          "Hart-Scott-Rodino Act" means the Hart-Scott-Rodino Antitrust
           ---------------------
Improvements Act of 1976, as amended.

          "Indemnification Agreement" means that Indemnification Agreement,
           -------------------------
dated the date hereof, between the Company, Walker and Purchaser.

          "Indemnified Party" has the meaning set forth in Section 7.3 of this
           -----------------
Agreement.

          "Indemnifying Party" has the meaning set forth in Section 7.3 of this
           ------------------
Agreement.

          "Intellectual Property Rights" has the meaning set forth in Section
          ------------------------------
3.16 of this Agreement.

          "IRS" means the Internal Revenue Service.
           ---

          "Lender Warrants" means the warrants which may be issued pursuant to
           ---------------
the Credit Agreement.

          "Letter Agreement" means that letter agreement between the Company and
           ----------------
Time Inc., substantially in the form attached hereto as Exhibit F.
                                                        ---------

          "Lien" means any mortgage, deed of trust, pledge, hypothecation,
           ----
assignment, encumbrance, lien (statutory or other) or preference, priority,
right or other security interest or preferential arrangement of any kind or
nature whatsoever (excluding preferred stock and equity related preferences),
including, without limitation, those created by, arising under or evidenced by
any conditional sale or other title retention agreement, the interest of a
lessor under a Capital

                                       3
<PAGE>

Lease Obligation, or any financing lease having substantially the same economic
effect as any of the foregoing.

          "Losses" has the meaning set forth in Section 7.1 of this Agreement.
           ------

          "Nonvoting Common Stock" means the Company's Class B common stock, par
           ----------------------
value $0.001 per share.

          "Orders" has the meaning set forth in Section 3.2 of this Agreement.
           ------

          "Permitted Liens" has the  meaning set forth in Section 3.15 of this
          -----------------
Agreement.

          "Person" means any individual, firm, corporation, partnership, trust,
           ------
incorporated or unincorporated association, joint venture, joint stock company,
limited liability company, Governmental Authority or other entity of any kind,
and shall include any successor (by merger or otherwise) of such entity.

          "Purchase Price" has the meaning set forth in the recitals to this
           --------------
Agreement.

          "Purchased Shares" has the meaning set forth in the recitals of this
           ----------------
Agreement.

          "Purchaser Indemnified Party" has the meaning set forth in Section 7.1
           ---------------------------
of this Agreement.

          "Purchaser" has the meaning set forth in the recitals to this
           ---------
Agreement.

          "Registration Rights Agreement" means the Second Amended and Restated
           -----------------------------
Registration Rights Agreement substantially in the form attached hereto as

Exhibit B.
---------

          "Requirement of Law" means, as to any Person, any law, statute,
           ------------------
treaty, rule, regulation, right, privilege, qualification, license or franchise
or determination of an arbitrator or a court or other Governmental Authority or
stock exchange, in each case applicable or binding upon such Person or any of
its property or to which such Person or any of its property is subject or
pertaining to any or all of the transactions contemplated or referred to herein.

          "Restated Charter" means the Restated Certificate of Incorporation
           ----------------
adopted by the Board of Directors and filed with the Secretary of State of the
State of Delaware on or before the date hereof substantially in the form
attached hereto as Exhibit C.
                   ---------

          "Securities Act" means the Securities Act of 1933, as amended, (or any
           --------------
successor statute thereto) and the rules and regulations of the Commission
thereunder.

          "Series A Preferred Stock" means the Company's Series A Convertible
           ------------------------
Preferred Stock, par value $0.001 per share.

          "Series B Preferred Stock" means the Company's Series B Convertible
           ------------------------
Preferred Stock, par value $0.001 per share.

                                       4
<PAGE>

          "Series C Preferred Stock" has the meaning set forth in the recitals
           ------------------------
to this Agreement.

          "Stockholders Agreement" means the Second Amended and Restated
           ----------------------
Stockholders Agreement substantially in the form attached hereto as Exhibit D.
                                                                    ---------

          "Subsidiaries" means, as of the relevant date of determination, with
           ------------
respect to any Person, a corporation or other Person of which 50% or more of the
voting power of the outstanding voting equity securities or 50% or more of the
outstanding economic equity interest is held, directly or indirectly, by such
Person. Unless otherwise qualified, or the context otherwise requires, all
references to a "Subsidiary" or to "Subsidiaries" in this Agreement shall refer
to a Subsidiary or Subsidiaries of the Company.

          "Tax", "Taxes" and "Tax Returns" have the meanings set forth in
           ---    -----       -----------
Section 3.9 of this Agreement.

          "Transaction Documents" means collectively, this Agreement, the
           ---------------------
Stockholders Agreement, the Registration Rights Agreement and the Restated
Charter.

          "Voting Common Stock" means the Company's Class A common stock, par
           -------------------
value $0.001 per share.

          "Walker" means Jay Walker.
           ------

          "Walker Sale Agreement" means that Securities Purchase Agreement,
           ---------------------
dated the date hereof, between Walker and Purchaser, pursuant to which Walker
has agreed to sell to Purchaser 6,875,000 shares of Voting Common Stock and
Nonvoting Common Stock for $8.00 per share.

          "Warrants" means those warrants to acquire Voting Common Stock issued
           --------
pursuant to the Stock and Warrant Purchase Agreement, dated as of January 12,
2000, between the Company and the Purchasers listed therein.

     1.2  Accounting Terms.  All accounting terms used herein not expressly
          ----------------
defined in this Agreement shall have the respective meanings attributed to them
in accordance with GAAP except that, if another meaning shall be specifically
set forth herein for any such term, such term shall have the meaning set forth
herein.

                                   ARTICLE 2

                 PURCHASE AND SALE OF SERIES C PREFERRED STOCK
                 ---------------------------------------------

     2.1  Purchase and Sale of Series C Preferred Stock.  Subject to the terms
          ---------------------------------------------
and conditions set forth herein, the Company agrees to issue and sell to
Purchaser, and Purchaser agrees that it will purchase from the Company at the
Purchase Price, on the Closing Date, the Purchased Shares.

                                       5
<PAGE>

     2.2  Restated Charter.  The Series C Preferred Stock shall have the
          ----------------
preferences and rights set forth in the Restated Charter.

     2.3  Closing.  The closing of the sale and purchase of the Purchased Shares
          -------
(the "Closing") shall take place at the Boston offices of Hale & Dorr LLP, at
      -------
10:00 a.m., local time, on the second Business Day after the conditions set
forth in Sections 5.7 and 6.2 hereof have been satisfied (but in no event  later
than June 30, 2000) or at such other time, place and date that the Company and
Purchaser may agree in writing (the "Closing Date").  On the Closing Date, the
                                     ------------
Company shall deliver to Purchaser a certificate representing the Purchased
Shares against delivery by Purchaser to the Company of the aggregate purchase
price therefor by wire transfer of immediately available funds.

                                   ARTICLE 3

                 REPRESENTATIONS AND WARRANTIES OF THE COMPANY

     Except as described in a disclosure schedule (the "Disclosure Schedule")
                                                        -------------------
attached hereto setting forth certain exceptions to the representations and
warranties described below, the Company represents and warrants to Purchaser, as
of the date hereof and as of the Closing Date,  as follows:

     3.1  Corporate Existence and Power.  The Company and each of its
          -----------------------------
Subsidiaries: (a) is a corporation duly organized, validly existing and in good
standing under the laws of the jurisdiction of its incorporation, (b) has all
requisite corporate power and authority to own and operate its property, to
lease the property it operates as lessee and to conduct the business in which it
is currently, or is proposed to be, engaged; and (c) is duly qualified as a
foreign corporation, licensed and in good standing under the laws of each
jurisdiction in which its ownership, lease or operation of property or the
conduct of its business require such qualification, except where such failure
would not result in a material adverse effect on the Condition of the Company.
The Company has the corporate power and authority to execute, deliver and
perform its obligations under this Agreement and each of the other Transaction
Documents to which it is a party.

     3.2  Authorization; No Contravention.  Except for the approval of the
          -------------------------------
stockholders of the Company, which will be obtained prior to the Closing, the
execution, delivery and performance by the Company of this Agreement and each of
the other Transaction Documents and the transactions contemplated hereby and
thereby: (a) have been duly authorized by all necessary corporate action of the
Company; (b) do not contravene the terms of the Restated Charter or the By-laws;
(c) do not violate, conflict with or result in any breach or contravention of,
or the creation of any Lien under, any material Contractual Obligation of the
Company, or any Requirement of Law applicable to the Company; and (d) do not
violate any judgment, injunction, writ, award, decree or order of any nature
(collectively, "Orders") of any Governmental Authority against, or binding upon,
                ------
the Company.

     3.3  Governmental Authorization; Third Party Consents.  Except for the
          ------------------------------------------------
consent of the Company's lender, Arena Capital Investment Fund, L.P., and
applicable requirements under the

                                       6
<PAGE>

Hart-Scott-Rodino Act, the Securities Act and state securities or blue sky laws,
no approval, consent, compliance, exemption, authorization or other action by,
or notice to, or filing with, any Governmental Authority or any other Person,
and no lapse of a waiting period under a Requirement of Law, is necessary or
required in connection with the execution, delivery or performance by, or
enforcement against, the Company of this Agreement and the other Transaction
Documents or the transactions contemplated hereby and thereby.

     3.4  Binding Effect.  This Agreement has been duly executed and delivered
          --------------
by the Company and, when executed, each of the other Transaction Documents will
be duly executed and delivered by the Company, and this Agreement and the other
Transaction Documents will constitute legal, valid and binding obligations of
the Company enforceable against the Company in accordance with their respective
terms.

     3.5  Litigation.  There are no actions, suits, proceedings, claims,
          ----------
complaints, disputes, arbitrations or investigations pending or, to the
knowledge of the Company, threatened, at law, in equity, in arbitration or
before any Governmental Authority against the Company or any of its
Subsidiaries. No Order has been issued by any court or other Governmental
Authority against the Company or any of its Subsidiaries purporting to enjoin or
restrain the execution, delivery or performance of this Agreement or any other
Transaction Document.

     3.6  Capitalization.
          --------------

          (a)  On the date hereof, the authorized capital stock of the Company
consists of: (i) 56,000,000 shares of Voting Common Stock, of which 7,368,000
shares are issued and outstanding; (ii) 36,000,000 shares of Nonvoting Common
Stock, of which 25,434,228 shares are issued and outstanding (assuming the
issuance of 62,500 shares of Nonvoting Common Stock to Richard Braddock); (iii)
2,600,000 shares of Series A Preferred Stock, of which 2,591,178.24 shares are
issued and outstanding; and (iv) 5,000,000 shares of Series B Preferred Stock,
all of which are issued and outstanding. All of the outstanding shares of
capital stock of the Company identified in this subsection (a) are validly
issued, fully paid and non-assessable.

          (b)  On the Closing Date, after giving effect to the transactions
contemplated by this Agreement, the authorized capital stock of the Company
shall consist of:  (i) 58,000,000 shares of Voting Common Stock, of which
7,368,000 shares shall be issued and outstanding; (ii) 37,000,000 shares of
Nonvoting Common Stock, of which 25,434,228 shares shall be issued and
outstanding; (iii) 2,600,000 shares of Series A Preferred Stock, of which
2,591,178.24 shares shall be issued and outstanding; (iv) 5,000,000 shares of
Series B Preferred Stock, all of which shall be issued and outstanding; and (v)
3,125,000 shares of Series C Preferred Stock, all of which shall be issued and
outstanding.  The Purchased Shares will be validly issued, fully paid and non-
assessable.

          (c)  Schedule 3.6 sets forth, at and on the Closing Date and assuming
               ------------
the consummation of the transactions contemplated by this Agreement, a true and
complete list of (i) the stockholders of the Company (including any trust or
escrow agent arrangement created in connection with any employee stock option
plan) and, opposite the name of each stockholder, the

                                       7
<PAGE>

amount of all outstanding capital stock owned by such stockholder and (ii) a
breakdown of all options outstanding under the Company's stock option plans,
grouped by the year in which such options vest, and describing the exercise
prices of such options.

          (d)  The Company has reserved an aggregate of 48,609,069.24 shares of
Voting Common Stock for issuance upon conversion of the Common Stock
Equivalents.  Except for the Warrants and the Lender Warrants, and except as set
forth on Schedule 3.6, there are no options, warrants, conversion privileges,
         ------------
subscription or purchase rights or other rights presently outstanding to
purchase or otherwise acquire (i) any authorized but unissued, unauthorized or
treasury shares of the Company's capital stock or the capital stock of any of
its Subsidiaries, (ii) any Common Stock Equivalents or (iii) other securities of
the Company or of any of its Subsidiaries.

          (e)  Prior to the Closing Date, the Purchased Shares shall have been
duly authorized, and when issued and sold to Purchaser after payment therefor in
accordance herewith, will be validly issued, fully paid and nonassessable and,
assuming the accuracy of the representations and warranties of Purchaser set
forth in Article 4, will be issued in compliance with the registration and
qualification requirements of all applicable federal and state securities laws
(or pursuant to exemptions therefrom).  Prior to the Closing Date, an aggregate
of 3,125,000 shares of Voting Common Stock issuable upon conversion of the
Purchased Shares shall have been duly reserved and authorized and, when issued
in compliance with the provisions of the Restated Charter, will be validly
issued, fully paid and nonassessable.

          (f)  The Company has no Subsidiaries and has no commitment or
obligation to acquire any capital stock or direct or indirect equity interest in
any corporation, partnership, limited liability company, joint venture or other
business entity, other than: (i) Synapse Solutions, Inc., a Delaware
corporation; NewSub Magazine Services, LLC, a Delaware limited liability
company; and SynapseConnect, Inc., a Delaware corporation; each of which is
wholly-owned by the Company; and (ii) Gift Services, LLC, a limited liability
company in which the Company has a 49% ownership interest. No person has any
right to purchase shares of capital stock or other equity interest in any
Subsidiary.

     3.7  Consolidated Financial Statements.  The Company has delivered to
          ---------------------------------
Purchaser its Audited Consolidated balance sheets as of December 31, 1999 and
1998 and the related consolidated statements of operations, stockholder deficit
and cash flows for each of the three years in the period ended December 31,
1999, a copy of which are attached as Schedule 3.7 hereto (the "Consolidated
                                      ------------              ------------
Financial Statements").  The Consolidated Financial Statements present fairly in
--------------------
all material respects the financial position of the Company and its Subsidiaries
as of December 31, 1999 and 1998 and the results of the Company's operations and
cash flows for each of the three years in the period ended December 31, 1999 in
conformity with GAAP.

     3.8  No Material Adverse Change; Ordinary Course of Business.  Since
          -------------------------------------------------------
December 31, 1999: (a) there has not been any material adverse change, nor to
the knowledge of the Company is any such change threatened, in the Condition of
the Company; (b) neither the Company nor any Subsidiary has participated in any
transaction or otherwise acted outside the ordinary course of business,
including, without limitation, declaring or paying any dividend or declaring or

                                       8
<PAGE>

making any distribution to its stockholders except as described in the
Disclosure Schedule; and (c) neither the Company nor any of its Subsidiaries has
increased the compensation of any of its officers or the rate of pay of any of
its employees, except as part of regular compensation increases in the ordinary
course of business.

     3.9   Taxes. Except as described in the Disclosure Schedule:  (a) the
           -----
Company and its Subsidiaries have paid or accrued all federal, state, county,
local, foreign and other taxes, including, without limitation, income taxes,
estimated taxes, excise taxes, sales taxes, use taxes, gross receipts taxes,
franchise taxes, employment and payroll related taxes, property taxes and import
duties, profits taxes, premium taxes, occupancy taxes, ad valorem taxes,
severance taxes, capital levy, production taxes, transfer taxes, withholding
taxes, unemployment compensation taxes, and other governmental charges and
assessments whether or not measured in whole or in part by net income, and
including deficiencies, interest, additions to tax or interest, and penalties
with respect thereto, and including expenses associated with disputing any
proposed adjustments relating to the foregoing (hereinafter, "Taxes" or,
                                                              -----
individually, a "Tax") which have come due, other than Taxes being disputed, in
                 ---
appropriate proceedings, by the Company or a Subsidiary in good faith for which
adequate reserves have been made in accordance with GAAP; (b) each of the
Company and the Subsidiaries has timely filed or caused to be timely filed all
tax returns, reports, forms and other such documents ("Tax Returns") that it is
                                                       -----------
required to file (including all applicable extensions), and all such Tax Returns
are accurate and complete in all material respects; (c) with respect to all Tax
Returns of the Company and each Subsidiary, (i) there is no unassessed Tax
deficiency proposed or, to the knowledge of the Company, threatened against the
Company or any Subsidiary, (ii) no audit is in progress, no extension of time is
in force with respect to any date on which any Tax Return was or is to be filed
and no waiver or agreement is in force for the extension of time for the
assessment or payment of any Tax, (iii) to the knowledge of the Company, there
has been no additional Tax assessment against the Company or any Subsidiary
heretofore proposed, and (iv) no waivers of the statute of limitation or
extension of time within which to assess any Tax have been heretofore granted by
the Company or any Subsidiary; and (d) there are no Liens for Taxes on the
assets of the Company or any Subsidiary except for Liens for Taxes not yet due.

     3.10  Disclosure.  This Agreement and the documents and certificates
           ----------
furnished to Purchaser by the Company, taken as a whole, do not contain any
untrue statement of a material fact or to the Company's knowledge omit to state
a material fact necessary in order to make the statements contained herein or
therein, in the light of the circumstances under which they were made, not
misleading.

     3.11  Private Offering.  No form of general solicitation or general
           ----------------
advertising was used by the Company or its representatives in connection with
the sale of the Purchased Shares.  Assuming the accuracy of the representations
and warranties of Purchaser set forth in Article 4, no registration of the
Purchased Shares, pursuant to the provisions of the Securities Act or any state
securities or "blue sky" laws, will be required by the sale of the Purchased
Shares.

     3.12  No Default or Breach; Contractual Obligations.  All of the
           ---------------------------------------------
Contractual Obligations which are material to the Condition of the Company are
valid, subsisting, in full force and effect and binding upon the Company and any
relevant Subsidiary, as applicable and,

                                       9
<PAGE>

to the best knowledge of the Company, upon each other party thereto and the
Company or its Subsidiary, as applicable, has paid in full or accrued all
amounts due thereunder and has satisfied in full or provided for all of its
liabilities and obligations thereunder in all material respects. To the
knowledge of the Company, no other party to any such Contractual Obligation is
in default thereunder, nor does any condition exist that with notice or lapse of
time or both would constitute a default by such other party thereunder. Neither
the Company nor any Subsidiary has received notice of any default under, nor are
they in default under or with respect to, any Contractual Obligation of the
Company or any relevant Subsidiary in any respect, which, individually or
together with all such defaults, could have a material adverse effect on (a) the
Condition of the Company or (b) the ability of the Company to perform its
obligations under this Agreement or the other Transaction Documents.

     3.13  Agreements.  Except as identified in the Disclosure Schedule, neither
           ----------
the Company nor any Subsidiary is a party to any written or oral contract not
made in the ordinary course of business and, whether or not made in the ordinary
course of business, neither the Company nor any Subsidiary is a party to any
written or oral:  (a) contract for the future purchase of fixed assets or for
the future purchase of materials, supplies or equipment in excess of normal
operating requirements; (b) contract for the employment of any officer,
individual employee or other person or any contract with any person on a
consulting basis or any offer letter providing for severance payments upon
termination of service; (c) employee benefit plan, as defined in Section 3(3) of
the Employee Retirement Income Security Act of 1974, as amended ("ERISA"), or
                                                                  -----
any other bonus, pension, profit-sharing, retirement, stock purchase, stock
option, deferred compensation, severance pay, salary continuation, dental,
disability, life insurance (including key man life insurance), hospitalization,
medical or similar plan, contract or understanding in effect with respect to
employees or former employees or any of their beneficiaries or dependents; (d)
agreement or indenture relating to the borrowing of money or to the mortgaging,
pledging or otherwise placing of a lien on any property or assets of the Company
or any Subsidiary; (e) guaranty of any obligation for borrowed money or
otherwise; (f) agreement or other commitment for capital expenditures in excess
of $250,000; (g) covenant not to compete; or (h) contract, agreement or
commitment under which the Company or any Subsidiary is obligated to repurchase
or otherwise acquire or retire any shares of the Company's Common Stock, the
common stock of any Subsidiary or any other capital stock of the Company or any
Subsidiary.  Neither the Company nor any Subsidiary is obligated under any
current contract, agreement or other obligation which, if performed fully by all
parties thereto, individually or in the aggregate, materially adversely affects,
or is reasonably likely to materially adversely affect, the Condition of the
Company.

     Each arrangement listed in Section 3.13(c) and (h) of the Disclosure
Schedule (collectively, the "Benefit Plans") has been administered in all
                             -------------
material respects in accordance with its terms.  On the date hereof, the Benefit
Plans are in all material respects in compliance with the applicable provisions
of ERISA and the Code, the rules and regulations promulgated thereunder, and all
other applicable laws.  There are no investigations by any governmental entity,
or other claims (except routine claims for benefits payable under the Benefit
Plans), suits or proceedings against or with respect to which any Benefit Plan
is a party or asserting any rights to or claims for benefits under any Benefit
Plan that would reasonably be expected to give rise to any material liability.
Neither the Company nor any Subsidiary has knowledge of any

                                       10
<PAGE>

involuntary termination proceedings instituted against any Benefit Plans.

     All contributions to, and payments from, the Benefit Plans that were
required to be made in accordance with the terms of the Benefit Plans have been
timely made. All premium payments that were required to be made in accordance
with the terms of the Benefit Plans or any underlying insurance contract have
been timely made in accordance therewith, except where such failure would not
result in material liability to the Company or a Subsidiary.

     Except as identified in the Disclosure Schedule, each Benefit Plan that is
intended to be a tax-qualified pension plan has been the subject of a favorable
determination letter from the IRS which was filed with the IRS within the
remedial amendment period prescribed under Section 401(b) of the Code with
respect to compliance with the Tax Reform Act of 1986 to the effect that such
pension plan is qualified under Section 401(a) of the Code, subject to the
customary reservations as to the plan's operational compliance with the Code's
requirements. No such determination letter has been revoked and, to the
knowledge of the Company or any Subsidiary, the IRS has not issued written
notice of its intent to revoke the qualified status of any such plan. Neither
the Company nor any Subsidiary has knowledge of any circumstances that would
reasonably be expected to result in disqualification of such pension plan.

     Neither the Company nor any Subsidiary maintains or contributes to, or has
ever in the past maintained or contributed to, (i) any plan or arrangement that
is intended to provide retiree medical benefits to its retired employees or
their beneficiaries or dependents except as required by applicable law, (ii) any
defined benefit pension plan that is required to meet the minimum funding
standards of Section 412 of the Code or Section 302 of ERISA, or (iii) a
multiemployer plan, as defined in Section 3(37) of ERISA.

     3.14  Labor Agreements and Actions.  Neither the Company nor any Subsidiary
           ----------------------------
is bound by or subject to any contract, commitment or arrangement with any labor
union, and to the Company's best knowledge, no labor union has requested, sought
or attempted to represent any employees, representatives or agents of the
Company or any Subsidiary. There is no strike or other labor dispute involving
the Company or any Subsidiary pending nor, to the Company's best knowledge,
threatened, nor is the Company aware of any labor organization activity
involving its employees or any employee of any Subsidiary.

     3.15  Properties.  Except for any properties which are leased, as to which
           -----------
the Company or a relevant Subsidiary have a valid leasehold interest, the
Company and each Subsidiary have good and marketable title to their properties,
both real and personal, in each case free from any Liens of any kind except (a)
tax or like liens for obligations not yet due or payable or being contested in
good faith by appropriate proceedings and for which appropriate reserves have
been established on the Company's or its Subsidiary's books, and (b) other
imperfections of title or Liens that do not impair in any material respect the
current or proposed use or marketability of the properties subject thereto ((a)
and (b) are referred to collectively as "Permitted Liens"). All such properties
that are necessary for the business of the Company or any Subsidiary as
presently conducted are maintained and kept in good condition, repair and
working order by the Company or a Subsidiary of the Company, subject to normal
wear and tear. Each of the Company and the Subsidiaries own, lease or license
all properties necessary for the conduct of their respective

                                       11
<PAGE>

businesses as presently conducted. With respect to real and personal property
that it leases, each of the Company and any Subsidiary, as applicable, hold
valid and enforceable leasehold interests free from all Liens except (i)
Permitted Liens and (ii) easements, covenants, rights of way and other Liens and
restrictions arising as a matter of law that do not impair in any material
respect the current use of the property subject thereto.

     3.16  Intellectual Property.
           ---------------------

           (a)  Except as identified in the Disclosure Schedule, the Company or
its Subsidiaries are either the sole and exclusive owner of, with all right,
title and interest in and to (free and clear of any Liens), or have a license to
use, all registered and unregistered trademarks, trademark registrations,
service marks, service mark registrations, domain names, domain name
registrations, trade names, company names, patents and copyrights and pending
applications therefor, in each case which are used in or required for the
business of the Company or any Subsidiary as currently being conducted and as
proposed to be conducted (together with all inventions, processes, computer
software, know-how, formulas, customer lists and trade secrets of the Company or
any Subsidiary, the "Intellectual Property Rights").
                     ----------------------------

           (b)  Except as identified in the Disclosure Schedule, all material
license agreements to which the Company or its Subsidiaries are a party which
give the Company or its Subsidiaries a license to use such Intellectual Property
Rights are perpetual licenses with annual license fees of less than $1,000. A
license agreement is material if a violation, infringement, termination or
expiration of such license agreement would have a material adverse effect on the
Condition of the Company.

           (c)  To the knowledge of the Company, neither the Company nor any
Subsidiary has violated or infringed any patent, copyright, trade secret,
trademark, service mark or other intellectual property right of any other Person
which violation or infringement would have a material adverse effect on the
Condition of the Company. Neither the Company nor any Subsidiary has been sued
or charged or been a defendant in any claim, suit, action or proceeding which
involves a claim of infringement of any patent, copyrights, trade secret,
trademark, service mark, or other intellectual property right of any other
Person which, if determined against the Company, would have a material adverse
effect on the Condition of the Company.

           (d)  Neither the Company nor any Subsidiary has made or asserted any
claim of violation or infringement of any Intellectual Property Rights against
any other Person, has any knowledge of any such violation or infringement or has
received any written communication alleging such infringement, which, if
determined against the Company, would have a material adverse effect on the
Condition of the Company.

     3.17  Interested Party Transactions.  Except for loans of less than $50,000
           -----------------------------
individually and $400,000 in the aggregate made by the Company to its employees
and except as identified in the Disclosure Schedule, (a) neither the Company nor
any Subsidiary has provided or caused to be provided any assets, services or
facilities or made any payments to any current or past officer, director,
employee or shareholder of the Company or any Subsidiary (or any affiliate of
any such individual) other than for current employment services, and (b) no
current or past officer,

                                       12
<PAGE>

director, employee or shareholder of the Company or any Subsidiary is presently,
or has been, directly or indirectly through such Persons' affiliation with any
other Person, a party to any agreement or transaction with the Company or any
Subsidiary other than in connection with any such Person's duties as an officer,
director, employee or shareholder of the Company or any Subsidiary.

     3.18  Registration Statement.  In the event that the Company completes an
           ----------------------
underwritten initial public offering of its equity securities pursuant to a
Registration Statement on Form S-1 filed under the Securities Act which has been
declared effective by the Securities and Exchange Commission (the "Form S-1"),
                                                                   --------
the information contained in such Form S-1 will be true and correct in all
material respects and will not omit to state any material fact necessary in
order to make the statements contained therein not misleading.

     3.19  Prior Subscription Documents.  The Company has delivered to Purchaser
           ----------------------------
true and complete copies of all documents pursuant to which the Series A
Preferred Stock and Series B Preferred Stock was issued to the purchasers
thereof.

     3.20  Broker's, Finder's or Similar Fees.  Other than amounts due to Allen
           ----------------------------------
& Company, Incorporated for its services to the Company in connection with the
sale of the Purchased Shares, there are no brokerage commissions, finder's fees
or similar fees or commissions payable by the Company or any Subsidiary in
connection with the transactions contemplated hereby based on any agreement,
arrangement or understanding with the Company or any Subsidiary or any action
taken by the Company or any Subsidiary.

                                   ARTICLE 4

                  REPRESENTATIONS AND WARRANTIES OF PURCHASER

     Purchaser hereby represents and warrants to the Company, as of the date
hereof and as of the Closing Date, as follows:

     4.1  Existence and Power.  Purchaser is a corporation duly organized,
          -------------------
validly existing and in good standing under the laws of the jurisdiction of its
formation and has all requisite corporate power and authority to execute,
deliver and perform its obligations under this Agreement and each of the other
Transaction Documents to which it is a party. All of the outstanding capital
stock of Purchaser is owned, directly or indirectly, by Time Inc.

     4.2  Authorization; No Contravention.  Except for the approval of the board
          -------------------------------
of directors of each of Purchaser, Time Inc. and Time Warner Inc., the
execution, delivery and performance by Purchaser of this Agreement and each of
the other Transaction Documents to which it is a party and the transactions
contemplated hereby and thereby: (a) have been duly authorized by all necessary
corporate action; (b) do not contravene the terms of Purchaser's organizational
documents or any amendment thereof; (c) do not violate, conflict with or result
in any breach or contravention of or the creation of any Lien under any
Contractual Obligation of Purchaser or any Requirement of Law applicable to
Purchaser; and (d) do not violate any Orders of any Governmental Authority
against, or binding upon, Purchaser.

                                       13
<PAGE>

     4.3  Governmental Authorization; Third Party Consents. Except for
          ------------------------------------------------
applicable requirements under the Hart-Scott-Rodino Act, the Securities Act and
state securities or blue sky laws, no approval, consent, compliance, exemption,
authorization, or other action by, or notice to, or filing with, any
Governmental Authority or any other Person, and no lapse of a waiting period
under any Requirement of Law is necessary or required in connection with the
execution, delivery or performance by, or enforcement against, Purchaser of this
Agreement and each of the other Transaction Documents or the transactions
contemplated hereby and thereby.

     4.4  Binding Effect.  This Agreement and each of the other Transaction
          --------------
Documents have been duly executed and delivered by Purchaser, and constitute the
legal, valid and binding obligations of Purchaser, enforceable against it in
accordance with their terms, except as enforceability may be limited by
applicable bankruptcy, insolvency, reorganization, fraudulent conveyance or
transfer, moratorium or similar laws affecting the enforcement of creditors'
rights generally or by equitable principles relating to enforceability
(regardless of whether considered in a proceeding at law or in equity).

     4.5  Purchase for Own Account.  The Purchased Shares to be acquired by
          ------------------------
Purchaser pursuant to this Agreement are being or will be acquired for
investment for its own account and with no intention of distributing or
reselling, or granting any participation in, such Purchased Shares or any part
thereof in any transaction that would be in violation of the securities laws of
the United States of America, or any state, without prejudice, however, to the
rights of Purchaser at all times to sell or otherwise dispose of all or any part
of such Purchased Shares under an effective registration statement under the
Securities Act, or under an exemption from such registration available under
such laws, and subject, nevertheless, to the disposition of Purchaser's property
being at all times within its control. If Purchaser should in the future decide
to dispose of any of such Purchased Shares, Purchaser understands and agrees
that it may do so only in compliance with the Securities Act and applicable
state securities laws, as then in effect. Purchaser agrees to the imprinting, so
long as required by law, of legends on certificates representing all of its
Purchased Shares as required by any applicable state securities laws and to the
following effect (and acknowledges that the Company will make a notation on its
transfer books to such effect):

     THE SECURITIES REPRESENTED BY THIS CERTIFICATE HAVE NOT BEEN REGISTERED
     UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE "ACT"), OR THE SECURITIES
     LAWS OF ANY JURISDICTION OF THE UNITED STATES. THE SECURITIES MAY NOT BE
     TRANSFERRED EXCEPT PURSUANT TO AN EFFECTIVE REGISTRATION STATEMENT UNDER
     SUCH ACT AND UNDER THE APPLICABLE STATE SECURITIES LAWS OR PURSUANT TO AN
     OPINION OF COUNSEL REASONABLY SATISFACTORY TO SYNAPSE GROUP, INC. (THE
     "COMPANY"), IF REQUESTED BY THE COMPANY, THAT THERE IS AN APPLICABLE
     EXEMPTION FROM THE REGISTRATION REQUIREMENTS OF SUCH ACT AND SUCH LAWS.

     THE SALE, ASSIGNMENT, HYPOTHECATION, PLEDGE, ENCUMBRANCE OR OTHER
     DISPOSITION (EACH A "TRANSFER") AND

                                       14
<PAGE>

     VOTING OF ANY OF THE SECURITIES REPRESENTED BY THIS CERTIFICATE ARE
     RESTRICTED BY THE TERMS OF THE SECOND AMENDED AND RESTATED STOCKHOLDERS
     AGREEMENT, DATED AS OF JUNE 23, 2000 (THE "STOCKHOLDERS AGREEMENT"), AMONG
     THE COMPANY AND THE STOCKHOLDERS NAMED THEREIN. THE COMPANY WILL NOT
     REGISTER THE TRANSFER OF SUCH SECURITIES ON THE BOOKS OF THE COMPANY UNLESS
     AND UNTIL THE TRANSFER HAS BEEN MADE IN COMPLIANCE WITH THE TERMS OF THE
     STOCKHOLDERS AGREEMENT. THE COMPANY WILL MAIL A COPY OF THE STOCKHOLDERS
     AGREEMENT, TOGETHER WITH A COPY OF THE EXPRESS TERMS OF THE SECURITIES AND
     THE OTHER CLASS OR CLASSES AND SERIES OF SHARES, IF ANY, WHICH THE COMPANY
     IS AUTHORIZED TO ISSUE, TO THE RECORD HOLDER OF THIS CERTIFICATE, WITHOUT
     CHARGE, WITHIN FIVE DAYS AFTER RECEIPT OF A WRITTEN REQUEST THEREFOR.

     4.6  Investment Experience.  Purchaser is an "Accredited Investor" as
          ---------------------
defined in Rule 501(a) under the Securities Act.

     4.7  Broker's, Finder's or Similar Fees.  There are no brokerage
          ----------------------------------
commissions, finder's fees or similar fees or commissions payable by Purchaser,
in connection with the transactions contemplated hereby based on any agreement,
arrangement or understanding with Purchaser or any action taken by Purchaser.

                                   ARTICLE 5

              CONDITIONS TO THE OBLIGATION OF PURCHASER TO CLOSE

     The obligation of Purchaser to purchase the Purchased Shares, to pay the
Purchase Price at the Closing and to perform its other obligations hereunder
shall be subject to the satisfaction as determined by, or waiver by, Purchaser
of the following conditions on the Closing Date.

     5.1  Representations; Secretary's Certificate.  The representations of the
          ----------------------------------------
Company set forth in this Agreement shall be true and correct on the Closing
Date and Purchaser shall have received a certificate to that effect from the
Company, in form and substance reasonably satisfactory to Purchaser, dated the
Closing Date and signed by the President of the Company. Purchaser shall have
received a certificate from the Company, in form and substance reasonably
satisfactory to Purchaser, dated the Closing Date and signed by the Secretary or
an Assistant Secretary of the Company, certifying that the attached copies of
the Restated Charter, the By-laws and resolutions of the Board of Directors
approving this Agreement and each of the other Transaction Documents and the
transactions contemplated hereby and thereby, are all true, complete and correct
and remain unamended and in full force and effect.

     5.2  Stockholders Agreement.  The Company and the stockholders named
          ----------------------
therein shall have duly executed and delivered the Stockholders Agreement.

                                       15
<PAGE>

     5.3  Registration Rights Agreement. The Company and the stockholders named
          -----------------------------
therein shall have duly executed and delivered the Registration Rights
Agreement.

     5.4  Filing of Restated Charter.  The Restated Charter shall have been duly
          --------------------------
filed by the Company with the Secretary of State of the State of Delaware in
accordance with the General Corporation Law of the State of Delaware.

     5.5  Purchased Shares.  The Company shall deliver to Purchaser at the
          ----------------
Closing a certificate in definitive form representing the Purchased Shares.

     5.6  Consents and Approvals.  All consents, exemptions, authorizations, or
          ----------------------
other actions by, or notices to, or filings with, Governmental Authorities and
other Persons in respect of all Requirements of Law and with respect to all
Contractual Obligations which are necessary or required in connection with the
execution, delivery or performance by, or enforcement against, the Company and
Purchaser of this Agreement and each of the other Transaction Documents shall
have been obtained and be in full force and effect and the Company shall have
been furnished with appropriate evidence thereof and all applicable waiting
periods shall have expired without any action being taken or threatened which
would have a material adverse effect on the Condition of the Company and, in
particular but without limitation, all applicable waiting periods (and any
extensions thereof) under the Hart-Scott-Rodino Act shall have expired or
otherwise been terminated.

     5.7  Receipt of Consolidated Financial Statements.  The Company shall have
          --------------------------------------------
delivered the Consolidated Financial Statements to Purchaser, in form and
substance reasonably satisfactory to Purchaser.

     5.8  Walker Sale Agreement.  Walker and Purchaser shall have duly executed
          ---------------------
and delivered the Walker Sale Agreement and the sale by Walker to Purchaser of
the shares of the Voting Common Stock and Nonvoting Common Stock described
therein shall be consummated in accordance with the terms of the Walker Sale
Agreement (subject to such waiver of any condition thereto as either party
thereto may grant in its sole discretion) simultaneously with the consummation
of the sale of the Purchased Shares hereunder.

     5.9  Amended and Restated Minor Shareholder Agreement.  The Company and the
          ------------------------------------------------
stockholders named therein shall have duly executed and delivered the Amended
and Restated Minor Shareholder Agreement.

     5.10 Director Approvals.  Purchaser shall have received the approval of
          ------------------
the board of directors of each of the companies indicated in Section 4.2 above.

     5.11 Letter Agreement.  The Company and Time Inc. shall have duly executed
          ----------------
and delivered the Letter Agreement.

     5.12 Purchaser Review of Financial Information.
          ------------------------------------------

          (a) The Company shall have made available to Purchaser on May 24, 2000
(or such other date as Purchaser may reasonably request) at the offices of the
Company in Stamford,

                                       16
<PAGE>

Connecticut all of the Company's books and records relating to the consolidated
financial statements of the Company and its subsidiaries for the quarter ended
March 31, 2000 for review by Purchaser. To the extent that competitive
information of the Company is being requested by Purchaser, the parties will
negotiate in good faith to agree upon the arrangements under which the Purchaser
may review such information. From such date until the Termination Date (as
defined below), (i) the Company shall have given Purchaser the opportunity to
hold discussions with such finance, accounting and management employees of the
Company as Purchaser may reasonably request in connection with such review and
(ii) if Purchaser so requests, the Company shall have arranged for appropriate
representatives of Arthur Andersen and Co. to provide Purchaser's outside
auditors with access to its working papers in connection with its audit of the
consolidated financial statements of the Company and its subsidiaries for 1999
and to hold discussions with Purchaser with respect thereto.

          (b)  Notwithstanding any provision hereof to the contrary, Purchaser
shall have the right to terminate this Agreement by written notice to the
Company, delivered to the Company by 5:00 PM on June 1, 2000 (the "Termination
Date"), to the effect that it elects to terminate this Agreement as a result of
unsatisfactory findings in the review described above or any material breach by
the Company of its covenants set forth in Section 5.12(a) above. Any election to
terminate this Agreement pursuant to the previous sentence shall be in the sole
discretion of Purchaser. In the event that the Closing does not occur as a
result of (i) Purchaser's election to terminate this Agreement as contemplated
in this Section 5.12 or (ii) the failure of any condition to the obligation of
Purchaser to close pursuant to Article V other than (y) the condition set forth
in Section 5.10, and (z), with respect to Sections 5.8 and 5.11, the failure by
Purchaser or Time Inc., as the case may be, to execute and deliver the
respective agreements, the Company shall reimburse Purchaser for one -half of
the filing fee paid by Purchaser in connection with its filing under the Hart-
Scott-Rodino Act in connection with this Agreement promptly upon written request
of Purchaser.

                                   ARTICLE 6

              CONDITIONS TO THE OBLIGATION OF THE COMPANY TO CLOSE
              ----------------------------------------------------

     The obligation of the Company to sell the Purchased Shares and to perform
its other obligations hereunder shall be subject to the satisfaction as
determined by, or waiver by, the Company of the following conditions on the
Closing Date.

     6.1  Payment by Purchaser.  Purchaser shall have paid the Purchase Price
          --------------------
for the Purchased Shares.

     6.2  Consents and Approvals.  All consents, exemptions, authorizations, or
          ----------------------
other actions by, or notices to, or filings with, Governmental Authorities and
other Persons in respect of all Requirements of Law and with respect to all
Contractual Obligations which are necessary or required in connection with the
execution, delivery or performance by, or enforcement against, the Company and
Purchaser of this Agreement and each of the other Transaction Documents shall
have been obtained and be in full force and effect and the Company shall have
been furnished with appropriate evidence thereof and all applicable waiting
periods shall have expired

                                       17
<PAGE>

without any action being taken or threatened which would have a material adverse
effect on the Condition of the Company and, in particular but without
limitation, all applicable waiting periods (and any extensions thereof) under
the Hart-Scott-Rodino Act shall have expired or otherwise been terminated.

     6.3  Walker Sale Agreement and Indemnification Agreement.  Walker and
          ---------------------------------------------------
Purchaser shall have duly executed and delivered the Walker Sale Agreement and
the Indemnification Agreement and the sale by Walker to Purchaser of the shares
of the Voting Common Stock and Nonvoting Common Stock described therein shall be
consummated in accordance with the terms of the Walker Sale Agreement (subject
to such waiver of any condition thereto as either party thereto may grant  in
its sole discretion) simultaneously with the consummation of the sale of the
Purchased Shares hereunder.

     6.4  Time Guarantee.  Time Inc. shall have executed and delivered the
          --------------
guarantee in the form attached as Exhibit E and the Company shall have received
                                  ---------
evidence reasonably satisfactory to the Company that such guarantee has been
duly authorized by all necessary corporate action by Time Inc.

     6.5  Director Approvals.  Purchaser shall have received the approval of the
          ------------------
board of directors of each of the companies indicated in Section 4.2 above.

     6.6  Letter Agreement.  The Company and Time Inc. shall have duly executed
          ----------------
and delivered the Letter Agreement.

                                   ARTICLE 7

                                INDEMNIFICATION
                                ---------------

     7.1  Indemnification by the Company.  Except as otherwise provided in this
          ------------------------------
Article 7, the Company agrees to indemnify, defend and hold harmless Purchaser
and its Affiliates and their respective officers, directors, agents, employees,
subsidiaries, partners, members and controlling persons (each, a "Purchaser
                                                                  ---------
Indemnified Party") to the fullest extent permitted by law from and against any
-----------------
and all losses and any and all actions, proceedings, claims, complaints,
disputes, arbitrations or investigations or written threats thereof
(collectively, "Claims") (including any Claim by a third party), damages,
                ------
expenses (including reasonable fees, disbursements and other charges of counsel
incurred by the Purchaser Indemnified Party in any action between the Company
and the Purchaser Indemnified Party or between the Purchaser Indemnified Party
and any third party or otherwise) or other liabilities (collectively, "Losses")
                                                                       ------
resulting from, arising out of or relating to the breach by the Company of any
representation or warranty or covenant set forth in Article 3 or from the breach
of any other agreement by the Company in this Agreement or the other Transaction
Documents, or from any allegation which, if true, would constitute such breach;

provided, that the Company shall not be liable under this Section 7.1 to a
--------
Purchaser Indemnified Party to the extent (and only to the extent) that it is
finally judicially determined that such Losses resulted primarily from the
material breach by such Purchaser Indemnified Party of any representation,
warranty, covenant or other agreement of such Purchaser Indemnified Party
contained in this Agreement or other Transaction Documents;

                                       18
<PAGE>

provided, further, that if and to the extent that such indemnification is
-----------------
unenforceable for any reason, the Company shall make the maximum contribution to
the payment and satisfaction of such Losses which shall be permissible under
applicable laws. Notwithstanding anything to the contrary contained herein, the
aggregate amount of all payments by the Company to the Purchaser Indemnified
Parties in respect of all Losses shall not exceed the Purchase Price. In
connection with the obligation of the Company to indemnify for expenses as set
forth above, the Company shall, upon presentation of appropriate invoices
containing reasonable detail, reimburse each Purchaser Indemnified Party for all
such expenses (including reasonable fees, disbursements and other charges of
counsel incurred by the Purchaser Indemnified Party). The Company acknowledges
that the Walker Sale Agreement provides for certain rights of indemnification of
the Purchaser Indemnified Parties by Walker in respect of the transactions
contemplated therein, including certain breaches by the Company of this
Agreement. Notwithstanding any provision of the Walker Sale Agreement or any
principles of law or equity that might otherwise require a Purchaser Indemnified
Party to resort to its rights against Walker in tandem with its resort to its
                                             -- ------
rights against the Company, the Company agrees that the provisions of this
Section 7.1 shall apply to the first $25,000,000 of Losses sustained, in the
aggregate, by the Purchaser Indemnified Parties to the same extent as if Walker
had not sold any shares of Common Stock to Purchaser. Nothing in this Article 7
shall restrict or limit any rights that any Purchaser Indemnified Party may have
against Walker under the Walker Sale Agreement.

     7.2  Indemnification by Purchaser.  Except as otherwise provided in this
          ----------------------------
Article 7, Purchaser agrees to indemnify, defend and hold harmless the Company
and its officers, directors, shareholders, agents, employees, subsidiaries,
partners, members and controlling persons (each, a "Company Indemnified Party")
                                                    -------------------------
to the fullest extent permitted by law from and against any and all Losses
resulting from, arising out of or relating to any breach of any representation
or warranty or covenant set forth in Article 4, or from any allegation which, if
true, would constitute such breach; provided, that Purchaser shall not be liable
                                    --------
under this Section 7.2 to a Company Indemnified Party to the extent (and only to
the extent) that it is finally judicially determined that such Losses resulted
primarily from the material breach by such Company Indemnified Party of any
representation, warranty, covenant or other agreement of such Company
Indemnified Party contained in this Agreement or the other Transaction
Documents; provided, further, that if and to the extent that such
           -----------------
indemnification is unenforceable for any reason, Purchaser shall make the
maximum contribution to the payment and satisfaction of such Losses which shall
be permissible under applicable laws.  Notwithstanding anything to the contrary
contained herein, the aggregate amount of all payments by Purchaser to the
Company Indemnified Parties in respect of all Losses shall not exceed the
Purchase Price.  In connection with the obligation of  Purchaser to indemnify
for expenses set forth above, Purchaser shall, upon presentation of appropriate
invoices containing reasonable detail, reimburse the Company for all such
expenses (including reasonable fees, disbursements and other charges of counsel
incurred by the Company.)

     7.3  Notification.  Each Purchaser Indemnified Party or Company Indemnified
          ------------
Party, as the case may be (for purposes of this Section 7.3, an "Indemnified
                                                                 -----------
Party"), under this Article 7 shall, promptly after the receipt of notice of the
-----
commencement of any action, investigation, claim or other proceeding against
such Indemnified Party in respect of which indemnity may be sought from the
Company or Purchaser, as the case may be (an "Indemnifying Party"), under this
                                              ------------------

                                       19
<PAGE>

Article 7, notify the Indemnifying Party in writing of the commencement thereof.
The omission of any Indemnified Party to so notify the Indemnifying Party of any
such action shall not relieve the Indemnifying Party from any liability which it
may have to such Indemnified Party (a) other than pursuant to this Article 7 or
(b) under this Article 7 unless, and only to the extent that, such omission
results in the Indemnifying Party's forfeiture of substantive rights or
defenses.  In case any such action, claim or other proceeding shall be brought
against any Indemnified Party, and it shall notify the Indemnifying Party of the
commencement thereof, the Indemnifying Party shall be entitled to assume the
defense thereof at its own expense, with counsel satisfactory to such
Indemnified Party in its reasonable judgment; provided, however, that any
                                              -----------------
Indemnified Party may, at its own expense, retain separate counsel to
participate in such defense at its own expense.  Notwithstanding the foregoing,
in any action, claim or proceeding in which both the Indemnifying Party, on the
one hand, and an Indemnified Party, on the other hand, are, or are reasonably
likely to become, a party, such Indemnified Party shall have the right to employ
separate counsel at the expense of the Indemnifying Party and to control its own
defense of such action, claim or proceeding if, in the reasonable opinion of
counsel to such Indemnified Party, a conflict or potential conflict exists
between the Indemnifying Party, on the one hand, and such Indemnified Party, on
the other hand, that would make such separate representation advisable;
provided, however, that the Indemnifying Party shall not be liable for the fees
-----------------
and expenses of more than one counsel to all Indemnified Parties.  The
Indemnifying Party agrees that it will not, without the prior written consent of
the Indemnified Party, settle, compromise or consent to the entry of any
judgment in any pending or threatened claim, action or proceeding relating to
the matters contemplated hereby (if any Indemnified Party is a party thereto or
has been actually threatened to be made a party thereto) unless such settlement,
compromise or consent includes an unconditional release of each Indemnified
Party from all liability arising or that may arise out of such claim, action or
proceeding.  The Indemnifying Party shall not be liable for any settlement of
any claim, action or proceeding effected against an Indemnified Party without
the Indemnifying Party's written consent, which consent shall not be
unreasonably withheld.  The rights accorded to an Indemnified Party hereunder
shall be in addition to any rights that any Indemnified Party may have at common
law, by separate agreement or otherwise; provided, however, that notwithstanding
                                         -----------------
the foregoing or anything to the contrary contained in this Agreement, nothing
in this Article 7 shall restrict or limit any rights that any Indemnified Party
may have to seek equitable relief.

                                   ARTICLE 8

                     BOARD REPRESENTATION; OBSERVER STATUS
                     -------------------------------------

     In the event that Purchaser's right pursuant to Section 6.4(c) of the
Stockholders Agreement to designate a representative for election to the Board
of Directors or a Time Observer (as defined in the Stockholders Agreement)
terminates as a result of the termination of the Stockholders Agreement pursuant
to Section 9.11 thereof, for so long as Purchaser and/or any Affiliate thereof
in the aggregate own shares of Common Stock or Common Stock Equivalents that
represent (after giving effect to any adjustment) at least three percent (3%) of
the total number of shares of Common Stock outstanding on a fully diluted basis,
Purchaser shall have the right to designate one representative to be nominated
as a management nominee to the Board of Directors. In the event that Purchaser
does not so designate a representative to be

                                       20
<PAGE>

nominated as a management nominee or such representative is not elected as a
director of the Company for any reason, for so long as Purchaser and/or any
Affiliate thereof has the right to so designate such a representative, Purchaser
may, from time to time upon notice to the Company, appoint a representative to
attend meetings of the Board of Directors or any committee thereof as a Time
Observer. The Time Observer shall not be entitled to vote at any meetings of the
Board of Directors. Except as contemplated by Section 6.7 of the Stockholders
Agreement, the Time Observer shall not have any duties, responsibilities or
liability by virtue of attendance at such meetings or the failure to attend the
same. The Company shall notify the Time Observer of all Board of Directors
meetings at the same time as the Company notifies directors of such meetings and
the Time Observer shall be entitled to receive all written materials directors
are entitled to receive. The Time Observer shall be indemnified by the Company
for his acts and omissions in such capacity to the same extent as directors of
the Company are indemnified for their acts and omissions as directors of the
Company and, to the extent possible, shall be afforded coverage under the
Company's errors and omissions insurance policy as an additional named insured.
Upon the election of a representative of Purchaser to the Board of Directors as
contemplated above, Purchaser shall not be entitled to appoint a Time Observer
until such time as such representative of Purchaser is no longer serving as a
director of the Company.

                                   ARTICLE 9

                                 MISCELLANEOUS
                                 -------------

     9.1  Survival of Representations and Warranties.  Except for the
          ------------------------------------------
representations and warranties set forth in Sections 3.1, 3.2, 3.3, 3.4, 3.6,
3.7, 3.9, 3.20, 4.1, 4.2, 4.4, 4.5, 4.6 and 4.7 herein, which shall survive the
execution and delivery of this Agreement without temporal limitation, any
investigation by or on behalf of the Company or Purchaser, or acceptance of the
Purchased Shares or termination of this Agreement, all of the representations
and warranties made herein shall survive the execution and delivery of this
Agreement, any investigation by or on behalf of the Company or Purchaser, or
acceptance of the Purchased Shares or termination of this Agreement until forty-
five (45) days after receipt by Purchaser of the Audited Financial Statements of
the Company for the fiscal quarter ending October 31, 2001.

     9.2  Notices.  All notices, demands and other communications provided for
          -------
or permitted hereunder shall be made in writing and shall be by registered or
certified first-class mail, return receipt requested, telecopier, courier
service or personal delivery to the addresses set forth below:

               (a)  if to the Company:

                    Synapse Group, Inc.
                    4 High Ridge Park
                    Stamford, CT  06905-1325
                    Attention:  Mr. Michael Loeb

                    with a copy to:
                    Hale and Dorr LLP

                                       21
<PAGE>

                    60 State Street
                    Boston, MA  02109
                    Attention:  John H. Chory, Esq.

               (b)  if to Purchaser:

                    NSSI Holdings Inc.
                    c/o Time Inc.
                    1271 Avenue of the Americas
                    New York, NY  10020
                    Attention:  Mr. Jeremy Koch

                    with a copy to:

                    Time Inc.
                    1271 Avenue of the Americas
                    New York, NY 10020
                    Attention: General Counsel

                         and

                    Patterson, Belknap, Webb & Tyler LLP
                    1133 Avenue of the Americas
                    New York, New York 10036
                    Attention: John P. Schmitt, Esq.

All such notices and communications shall be deemed to have been duly given when
delivered by hand, if personally delivered; when delivered by courier, if
delivered by commercial courier service; five (5) Business Days after being
deposited in the mail, postage prepaid, if mailed; and when receipt is
mechanically acknowledged, if properly telecopied.

     9.3  Successors and Assigns; Third Party Beneficiaries.  This Agreement
          -------------------------------------------------
shall inure to the benefit of and be binding upon the successors and permitted
assigns of the parties hereto.  Subject to applicable securities laws, Purchaser
may assign any of its rights under this Agreement to any of its Affiliates upon
notice to the Company.  The Company may not assign any of its rights under this
Agreement without the written consent of Purchaser.  Except as provided in
Article 7, no Person other than the parties hereto and their successors and
permitted assigns is intended to be a beneficiary of this Agreement.

     9.4  Amendment and Waiver.
          --------------------

          (a) No failure or delay on the part of the Company or Purchaser in
exercising any right, power or remedy hereunder shall operate as a waiver
thereof, nor shall any single or partial exercise of any such right, power or
remedy preclude any other or further exercise thereof or the exercise of any
other right, power or remedy.  The remedies provided for herein are

                                       22
<PAGE>

cumulative and are not exclusive of any remedies that may be available to the
Company or Purchaser at law, in equity or otherwise.

          (b) Any amendment, supplement or modification of or to any provision
of this Agreement, any waiver of any provision of this Agreement, and any
consent to any departure by the Company or Purchaser from the terms of any
provision of this Agreement, shall be effective only if it is made or given in
writing and signed by the Company and Purchaser.

     9.5  Counterparts.  This Agreement may be executed in any number of
          ------------
counterparts and by the parties hereto in separate counterparts, each of which
when so executed shall be deemed to be an original and all of which taken
together shall constitute one and the same agreement.

     9.6  Headings.  The headings in this Agreement are for convenience of
          --------
reference only and shall not limit or otherwise affect the meaning hereof.

     9.7  Pronouns.  All pronouns and any variations thereof refer to the
          --------
masculine, feminine or neuter, singular or plural, as the context may require.

     9.8  GOVERNING LAW; JURISDICTION.  THIS AGREEMENT SHALL BE GOVERNED BY AND
          ---------------------------
CONSTRUED IN ACCORDANCE WITH THE LAWS OF THE STATE OF NEW YORK, WITHOUT REGARD
TO THE PRINCIPLES OF CONFLICTS OF LAW OF ANY JURISDICTION.  The parties hereto
agree that any suit, action or proceeding instituted against either of them with
respect to this Agreement (including any exhibits hereto) shall be brought in
any federal or state court located in New York, New York.  The parties hereto,
by the execution and delivery of this Agreement, irrevocably waive any objection
or defense to the institution of any action in New York, New York based on
improper venue, the convenience of the forum or the jurisdiction of such courts,
or to the execution of judgments resulting therefrom, and the parties hereto
irrevocably accept and submit to the jurisdiction of the aforesaid courts in any
suit, action or proceeding and consent to the service of process by certified
mail at the address set forth in Section 9.2 hereof.

     9.9  Severability.  If any one or more of the provisions contained herein,
          ------------
or the application thereof in any circumstance, is held invalid, illegal or
unenforceable in any respect for any reason, the validity, legality and
enforceability of any such provision in every other respect and of the remaining
provisions hereof shall not be in any way impaired, unless the provisions held
invalid, illegal or unenforceable shall substantially impair the benefits of the
remaining provisions hereof.

     9.10 Entire Agreement.  This Agreement, together with the exhibits and
          ----------------
schedules hereto and the other Transaction Documents, is intended by the parties
as a final expression of their agreement and intended to be a complete and
exclusive statement of the agreement and understanding of the parties hereto in
respect of the subject matter contained herein and therein.  There are no
restrictions, promises, warranties or undertakings, other than those set forth
or referred to herein or therein.  This Agreement, together with the exhibits
hereto, and the other

                                       23
<PAGE>

Transaction Documents supersede all prior agreements and understandings between
the parties with respect to such subject matter.

     9.11  Fees.  Each of the parties hereto shall bear its own costs and
           ----
expenses incurred in connection with the transactions contemplated by the
Transaction Documents, including, without limitation, its fees, disbursements
and other charges of counsel.

     9.12  Publicity.  Except as may be required by any applicable Requirement
           ---------
of Law, none of the parties hereto shall issue a publicity release or public
announcement or otherwise make any public disclosure concerning this Agreement
or the transactions contemplated hereby, without prior approval by the other
parties hereto (which approval shall not be unreasonably withheld); provided,
                                                                    ---------
however, that nothing in this Agreement shall restrict Purchaser from disclosing
-------
information:  (a) that is already publicly available; (b) to the prospective
transferee in connection with any contemplated transfer of any of the Purchased
Shares; and (c) to its attorneys, accountants, consultants and other advisors to
the extent necessary to obtain their services in connection with Purchaser's
investment in the Company.  If any announcement is required by any applicable
Requirement of Law to be made by any party hereto, prior to making such
announcement such party will deliver a draft of such announcement to the other
parties and shall give the other parties an opportunity to comment thereon.

     9.13  Further Assurances.  Each of the parties shall execute such documents
           ------------------
and perform such further acts (including, without limitation, obtaining any
consents, exemptions, authorizations or other actions by, or giving any notices
to, or making any filings with, any Governmental Authority or any other Person,
and otherwise fulfilling, or causing the fulfillment of, the conditions to
Closing set forth in Articles 5 and 6) as may be reasonably required or
desirable to carry out or to perform the provisions of this Agreement and to
consummate and make effective as promptly as possible the transactions
contemplated by this Agreement.

               [Remainder of this page intentionally left blank]

                                       24
<PAGE>

     IN WITNESS WHEREOF, the parties hereto have caused this Agreement to be
executed and delivered by their respective officers hereunto duly authorized on
the date first above written.

                         the "Company"

                         SYNAPSE GROUP, INC.

                         By: /s/ Michael R. Loeb
                             -------------------
                             Name: Michael Loeb
                             Title: President

                         "Purchaser"

                         NSSI HOLDINGS INC.

                         By: /s/ Jeremy B. Koch
                             ------------------
                             Name: Jeremy B. Koch
                             Title:  President

                                       25

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