Made of Honor

On Halloween night, 1998, at Cornell University, Tom Bailey, Jr. (Patrick Dempsey), in costume as Bill Clinton, slips into bed with his pre-arranged date, Monica. It turns out to be the wrong woman, Monica's roommate Hannah (Michelle Monaghan), and Tom likes her because she is so honest and does not fling herself at him. Ten years later, Hannah and Tom are best friends. Tom is very wealthy because of his creation of the "coffee collar" and gets a dime every time it is used. Tom is with a different girl every week, while Hannah focuses on her career at the Metropolitan Museum of Art. He is very content with his life, suspecting that Hannah is too.