Tom and Hannah met in college when he accidentally slipped in her bed thinking she was her roommate. He was impressed how feisty and honest she was. He always had girls flinging themselves at him but Hannah was against all that. Tom (Patrick Dempsey) is successful in life. He's become wealthy from his invention of the "coffee collar", has plenty of guy friends to hang with, a new girl every week, and his one best friend. From the very start it's obvious this best friend is crazy about him and he takes her for granted. They go to antique stores together and guess each other desserts at a famous bakery. His best friend Hannah (Michelle Monaghan) goes to Scotland on an acquisition trip for her museum (though still manages to spend 4 out of her 6 weeks there sight seeing) and Tom realises he feels empty without her. All the girls he goes out with while she is gone complain about the antiques store or can't even play the dessert guessing game. Tom decides to tell Hannah his feelings and ask her to be with him when she returns in six weeks. Tom finds out Hannah has become engaged to a wealthy man, Colin (Kevin McKidd), in Scotland and plans to move there. Hannah asks Tom to be her "maid" of honor and he agrees so he can try to win Hannah back and stop the wedding. Tom decides to be the best maid of honor he possibly can be. He wants to show Hannah that she really doesn't know Colin all that well and that it was a mistake getting engaged so quickly. Hannah reveals that she is going to move to Scotland to be with Colin. While in Scotland, Tom plans to tell Hannah he loves her. They share a passionate kiss, then break away. Hannah then gets whisked off by her bridesmaids. That night, Hannah goes up to Tom's room to talk to him. But before she arrives, Hannah's cousin, who Tom broke up with, comes into Tom's room and attempts to seduce him. Hannah walks in right as Hannah's cousin is on top of Tom. Tom and Hannah have an argument, and Tom leaves for home. But on his way, he decides to stop the wedding. On horseback (borrowing a horse in exchange for part of his coffee collar royalties) he makes it to the chapel just in time, and kisses Hannah, who decides to cancel the marriage and marry Tom.