Build a movie plot around this: Is Tom Bailey, Jr.'s date with Monica pre-arranged? Yes
The answer to this question is:
One Halloween night, Tom Bailey (Patrick Dempsey) dressed as Bill Clinton goes to slip into bed with his pre-arranged date "Monica", but it was the wrong woman. Instead it was "Monica's" roommate Hannah (Michelle Monaghan). After bantering which each other, they become instant friends for Tom likes her honesty and how she doesn't fling herself at him.Ten years later we see Tom, very wealthy because of his creation of the "coffee collar" (gets a dime every time it is used) and leaving the bed of another girl. A different one every every night for one of his rules is "no back to backs except for Sundays and Mondays for they are a different week". After picking up two lattes at Starbucks and another phone number, Tom meets up with Hannah at a museum where she is a painter, and the two have lunch.Tom takes Hannah to his father's sixth wedding to a young girl who has more boobs than brains and after the reception Hannah tells Tom she must go to Scotland for work. While she's gone for those long agonizing months, Tom discovers that without her, and being with other women over and over is not very fulfilling. He soon realizes that he is in love with Hannah. During a basketball game he tells his friends his realization and get typical neanderthal responses from them, but decides to tell her his feelings after all when she gets back. However, after meeting up with Hannah at a restaurant, Hannah surprises Tom by introducing to him a wealthy Scotsman named Colin (Kevin McKidd) and announces that they are engaged, and incredibly asks Tom to be her "maid" of honor.After discussing it with his friend, Tom decides to be her maid of honor after all just to spend time with her. After meeting her pastor he tries to convince her she does not even know Colin and make her realize that she loves him but to no avail. Later they meet up with the other bridesmaids, one of them being Hannah's cousin and a bitter ex fling, who passes Tom a business card for entertainment for the shower. Later at the shower the business card was...