A hotshot thirtysomething record executive tries to win over the girl who once liked him only "as a friend" in this slapstick comedy. In high school, Chris Brander (Ryan Reynolds) was an overweight, maladroit teen who spent every waking moment with his co-ed pal Jamie Palamino (Amy Smart). On the verge of graduation, Chris is humiliated when his yearbook confession to Jamie -- that he wants to be more than "just friends" -- is read aloud. Jamie is flattered, but rebuffs his advances, and Chris spends the next decade transforming himself into a buff, callous ladies' man. Assigned by his boss to sign his pop star ex-girlfriend Samantha James (Anna Faris), Chris finds himself stranded in New Jersey for the holidays, where he promptly sets out to find Jamie. But winning back the love of his life proves difficult, as Chris not only has to get back in touch with the sensitive teen he once was, but also fend off competition from another former geek, the guitar-playing Dusty (Chris Klein).