Reynolds plays Chris, a former over-weight high school looser who has never really gotten over his high school sweetheart, Jamie (Amy Smart). Chris has tried to put his less than perfect New Jersey upbringing behind him but fate brings him back to his hometown during fateful holiday break.

He has had to go back to his roots as he is trying to sign the next big pop sensation, Samantha James (Anna Faris), to the label he works for as a successful, thin, record producer. Sam is crazy in all senses of the word and she makes Chris’s life a living hell but Chris is determined to sign her. To make matters worse, they used to sleep together.

Chris ends up in his hometown with the “nightmare princess” in tow while he tries to re-forge a relationship with his long lost high school sweetheart. Will Chris be able to make amends for the past years? How does Jamie look now after all these years? Does Chris still have feelings for this hometown girl, and does she have feelings for him?…