When Chris, a likable, high-school loser, finally gathers the courage to reveal his love to Jamie, the girl of his dreams, she rejects him, saying she just wants to be friends. So, he moves across the country and transforms himself into a selfish, womanizing and successful music executive. But, 10 years later, circumstances bring him back to his home town and fate reconnects him with the girl of his dreams. Suddenly, Chris has the chance to undo the past, but unbelievably, he finds it more difficult to romance Jamie than it was 10 years ago.