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Christina walters (Cameron Diaz) spent years avoiding men and then suddenly met her perfect match (Thomas Jane) while hanging out with her best girlfriends Courtney (Christina Applegate) and Jane (Selma Blair). Then she finds out that he left town. So she and Courtney set off on a trip.

When he confessed his love for his best friend during their formative high school years ago, Chris was met with a broken heart and a degrading humiliation. Only adding insult to injury was his larger than life frame which became a source of ridicule for cruel classmates. But years later and things having changed, Chris is now a hotshot record producer in Hollywood and the complete physical opposite of himself in high school. He’s also got an up and coming act by the name of Samantha James who has a psychotic crush on her producer. When a freak accident occurs on the way to Paris, Chris is forced to return home with her in tow. Little does he know that he would come face to face with the friend that he tried so desperately to forget. With the chance to woo her again, Chris will do what he can despite his client’s violent misgivings and a competitive rival suitor against him. No matter the crazy obstacles he must overcome, Chris will do whatever it takes to be more than just friends.

Kathryn makes a bet that her step-brother, Sebastian, won’t be able to bed Annette (a virgin, who wants to wait until marriage) before the start of the school year. If he loses, Kathryn gets his Roadster, if he wins, he gets Kathryn