The opening segments of the movie intersect between Andrew Paxton (Ryan Reynolds) and Margaret Tate (Sandra Bullock) as they wake up and get ready for the workday. While Margaret has time to work out and leisurely read the paper as she eats her breakfast, Andrew wakes to find he's overslept and leaps out of bed in a panic. Despite being late, he manages to pick up some coffee and rush into the office of a large publishing company in New York City just as his boss Margaret comes in. He fires off a mass mail warning everyone in their cubicles to look sharp as the 'witch on her broom' arrives. It turns out that Margaret is a top editor of the company, notorious for her cold indifference and iron fist, while Andrew is her assistant / secretary.Margaret begins the day by firing fellow editor Bob Spaulding (Aasif Mandvi) for failing to set up an interview with an author renowned for his reclusiveness. Bob responds by yelling at and insulting her in front of his coworkers, but this doesn't faze Margaret, who orders him to vacate the office by the end of the day and informs Andrew that, due to Bob's firing, she needs him to work over the weekend.Andrew explaining that he's planning to travel home for his grandmother's 90th birthday reaps no leeway. Margaret is then summoned to an upper office to speak with her boss, Chairman Bergen (Michael Nouri), who informs her that she is to be deported back to her native Canada due to an expired visa. When Andrew enters the office to fetch Margaret, she devises a desperate bid to stay in the country and maintain her job: She calls Andrew to her side and announces that the two are to be married. Andrew is too stunned and encouraged by Margaret's assurances to deny otherwise. Bergen arranges to have them go together to the immigration office to validate the engagement.Back in Margaret's office, Andrew tries to break away from the situation, but Margaret blackmails him into keeping the ruse up until she gains her citizenship, promising to swiftly divorce him once it's done. Despite his fears of being fined, or worse, sentenced to jail time, Andrew agrees. At immigration they meet with Mr. Gilbertson (Denis O'Hare), an investigator who sees through their ploy and tries to get them to confess. Though looking as though he will crack under the pressure, Andrew retains his composure and assures Gilbertson that he and Margaret are in love and that he's even due to be promoted to editor; doing a complete 180 on Margaret's blackmail. While Gilbertson is still unconvinced, Margaret insists and tells him they're planning to announce their engagement at Andrew's grandmother's birthday party that weekend, which turns out is in Sitka, Alaska.Once out on the street, Andrew demands that his promotion be immediate and tells Margaret to publish 20,000 copies of a manuscript he's been trying to get through or he will make a deal with immigration and confess. Trapped in her desperation, Margaret agrees and, upon Andrew's request, gets down on her knees and asks him to marry her. Andrew teases her but accepts.The first leg of their journey is in First Class on a transcontinental flight, during which Margaret quizzes Andrew's knowledge on her to find that he has been very thorough, while she knows nearly nothing about him. He reveals that he knows she has a tattoo since she once asked him to research removal techniques but canceled her dermatologist appointment. They are forced to take a second, smaller, and uncomfortable flight from Anchorage to Sitka. Upon landing they are greeted by Andrew's mother, Grace (Mary Steenburgen) and grandmother, Annie (Gammie - Betty White), who inform them that Margaret's hotel reservation was canceled so that she could stay at the family home.Margaret is clearly uncomfortable in this environment and, as they make their way to Andrew's home, is shocked to see that the family name is posted on nearly every business in town. She is equally shocked when she learns that the only way to get to the Paxton home is by boat. Since she can't swim, her fear is apparent, though Andrew tells her to shrug it off.Arriving at the family estate, Margaret questions why Andrew never told her he was rich. He plays it off by saying that he isn't but his family is. Inside they find a large gathering of family and friends waiting for them as a homecoming to Andrew, who's been away for three years. To Andrew's surprise, his friend Chuck (Michael Mosley) and high school sweetheart Gertrude (Malin Akerman) are in attendance.Andrew's father, Joe (Craig T. Nelson), confronts him about bringing his boss about whom Andrew consistently expressed hatred in the past. Having been estranged from his father for some time, Andrew defiantly declares his intent to marry Margaret before announcing the engagement to everyone. Joe is stunned but Grace and Gammie react with joy and request a story of the proposal. Andrew and Margaret improvise an awkward story of how it happened, playing off each other and laying subtle insults throughout. Clinking their wine glasses, everyone demands a kiss from Andrew and Margaret who oblige with a light peck at first but finish with a longer, passionate kiss that seems to surprise the both of them.Reassuring them that she approves their relationship, Grace sets Andrew and Margaret up together in a shared bedroom for the night. Gammie gives Margaret a quilt with 'special powers' that she won't divulge other than saying she's nicknamed it The Babymaker. Margaret tosses it aside for the night and insists that Andrew sleep on the floor.The next morning, Margaret is awoken by her phone and sees that one of her important clients is calling. She struggles for better reception and is told by Andrew, half asleep, to go outdoors. As she exits, she fails to shut the front door and the family puppy, a husky named Kevin, follows her out only to be swept up by a hungry eagle, which drops Kevin into Margaret's arms and swoops in again, snatching her phone right out of her hand. Margaret lifts Kevin in the air in a comical attempt to trade the puppy for her phone while Grace and Gammie watch from inside, thinking she's merely playing. Andrew goes outside to fetch her and tells her that he can place an order for a new phone to pick up in town. For now, he tells her that she's going out with his mother and Gammie, who take her to a local bar where they watch as Ramone (Oscar Nuñez), who Margaret recognizes as the man who was waiting hors d'oeuvres at the Paxton home, performs a dance to a remix of Relax. He places a veil on Margaret's head and brings her to the stage for a bachelorette strip dance, much to her embarrassment.Margaret steps outside for some air once her lap dance is over, and is soon joined by Gertrude. They talk about Andrew, and Gertrude reveals that he proposed to her after graduation, but she refused because he wanted to go to the city and she wanted to stay home. She's happy being an eternal local and always knew that Andrew was meant for bigger things. Grace comes outside to collect Margaret and, through the open door, Gammie is briefly seen dancing with Ramone.Back at the house, Andrew goes outside where his father is driving golf balls that dissolve in water into the lake. While Joe apologizes for his rash behavior over the engagement, he expresses his disappointment that Andrew chose to move to New York rather than run the family empire, berating his career choice as trivial and silly. Andrew argues that what he does makes him happy before rejecting his father's apology and leaving. When Grace, Gammie, and Margaret return, they find Andrew listening to an MP3 and hollowing out a wooden canoe in the yard, which Grace recognizes as a sign that something is wrong, as evidently the canoe has been a long-term project that Andrew usually works on when upset.Grace confronts Joe in the lounge and tells him to start being more supportive before Andrew decides not to come home again. Margaret overhears some of the dispute before going upstairs to shower. Just before she gets out of the shower, Andrew enters the room, still listening to his music, and walks out to the balcony where he starts to undress. Realizing that she forgot to grab a towel from the linen closet, Margaret tries to sneak out of the bathroom but is pestered by Kevin. As she makes a break for it, she runs straight into the naked Andrew and they collapse to the floor. Screaming at each other, they quickly cover up and run to opposite ends of the room and Margaret barely avoids using the Babymaker as a cover-up.Later that night, they lie awake and Margaret asks Andrew why relations with his father are so strained. Andrew eludes the question and changes the subject to Margaret and what she has a tattoo of on her back. Silent at first, Margaret tells him that she has two swallows meant to immortalize her parents, who died when she was sixteen. She warms up further and explains that she only acts tough to maintain a reputation; when Bob shouted insults at her, she retreated to the restroom where she wept. Andrew breaks the somber mood by singing It Takes Two by Margaret's favorite band and then asks her not to take it wrongly when he says she's very attractive.The next morning, Margaret wakes early and puts on some light makeup before Grace knocks on the door. Margaret frantically tries to wake Andrew and make it appear as though they'd been snuggling as Grace enters with Joe and Gammie and asks them if they will marry the next day in the barn where they were wed. Andrew and Margaret hesitate but quickly agree when Gammie asks if they could do so before she dies.The sudden decision puts Andrew into shock and he fears that if Gammie finds out about the charade, she will die. Margaret tries to console him, finding herself in a more caring mood before she leaves the room to change. Scared by her feelings, Margaret grabs a bike and heads down a trail in the woods where she happens upon Gammie chanting around a small fire, dressed in traditional native robes. Gammie invites Margaret to chant to Mother Earth to ask for blessing and encourages her to find a rhythm. Margaret starts chanting and to Gammie's surprise, breaks into singing Get Low. Andrew arrives and tells Margaret that her phone has arrived in town.They retrieve the phone at a convenience store, where Margaret is shocked to see Ramone working. Andrew takes her to an Internet café to check her mail while he runs outside to catch up with Gertrude, who is escorting a class of children while Margaret watches them with mixed feelings.Leaving the café, Margaret is kidnapped by Grace and Gammie, who take her to a dress shop where she is fitted with Gammie's wedding dress. Gammie does the alterations and gives Margaret a necklace that was given to her by her mother. Margaret is visibly moved by this and Grace breaks down with happiness.Afterwards Margaret meets Andrew at the docks to go back to the house but takes the controls and speeds off. Andrew asks her what's wrong and Margaret panics and shouts that she'd forgotten what it was like to have a real family; the idea of falsely marrying and possibly hurting Andrew's family now seems impossible. Andrew takes the helm of the boat back and narrowly misses a buoy, but the sharp turn sends Margaret overboard. Andrew manages to rescue her and take her back to the house safely. However, they are met on the docks by Joe, who takes them to the barn where Mr. Gilbertson the immigration agent is waiting. They both confront the couple on the possibility of a false marriage, but Andrew stands by his word and angrily leaves the barn with Margaret.Later, Margaret tries to tell Andrew that he should reconsider his actions, but he is adamant. Before they can do anything else, Gammie steals Andrew away saying that the groom must not see his bride before the wedding.The next day, everything goes as planned until Margaret is standing at the altar with Andrew facing the ubiquitous cleric, Ramone. Before he can start, Margaret stops him and, over Andrew's objections, faces the crowd and announces the farce. Mr. Gilbertson smiles in his seat as Margaret apologizes to the Paxton family and tells Gilbertson to meet her at the airport. Andrew goes to follow Margaret, but is stopped by his family demanding an explanation. By the time he gets to their bedroom, Margaret is gone. Her wedding dress and a hand-written note lie on the bed. He reads the note, an apology from Margaret acknowledging his writing talents and promising that she will keep her end of the bargain, as Gertrude enters. Though Andrew seems upset and tells Gertrude that Margaret was inconsiderate to leave without talking to him face to face, she asks him if he's simply going to let her go.Andrew runs back outside and is stopped by his father, who quarrels with him over what's happened. Gammie stammers in the background for them to stop yelling and suddenly gets short of breath and collapses. An emergency charter plane is called to take Gammie to the hospital. Grace, Joe, and Andrew accompany her and she asks the boys to make up with each other and to stop fighting. They promise to, and she lays back, content, and says the spirits can now take her. Then she sits up and announces,"I guess they're not ready for me!" before ordering the pilot to take them to the airport. Joe and Andrew are beside themselves, but Gammie defends herself saying that her dying act was the only way to get them to shut up.They arrive at the airport and Andrew dashes onto the runway but is too late to stop Margaret's plane. Joe can only express confusion while Grace and Gammie explain that Margaret wouldn't have told the truth unless she loved Andrew, who has discovered that he loves her too.With 24 hours to pack and depart to Canada, Margaret cleans out her office as coworkers still show trepidation around her, though she couldn't care less at this point. Andrew arrives, out of breath and out of patience. He tells her that, while only three days ago he fantasized about her getting hit by a taxi, things started to change in Alaska and he only realized how he truly felt when he was left alone at the altar. He properly proposes and, while Margaret admits that she's scared, accepts. They kiss and are applauded by the whole office.They return to the immigration office where Gilbertson tells them that if they show the slightest hint that their engagement this time isn't genuine, he will take them down. As the credits roll, Margaret and Andrew, along with the entire Paxton family, are individually interviewed by the Gilbertson with comical results. Ramone is also interviewed and he laughs nervously as his citizenship is questioned.
Output: Question: What did Margaret learns from Gertrude that Andrew wanted to be?, Answer: Andrew wanted to marry Getrude