High school student Chris Brander (Ryan Reynolds) loves his best friend, Jamie Palamino (Amy Smart). He finally confesses his feelings, but she tells him that she just wants to be friends, and he leaves town in shame. Ten years later, Chris is a successful record executive and involved with self-absorbed pop star Samantha James (Anna Faris). He still pines for Jamie, though, and when his plans to go to Paris for the holidays fall through, he returns to his hometown to try and win her heart.