High school student Chris Brander loves his best friend, Jamie Palamino . 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 . 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.