Just Friends (2006)

Back in high school, Chris was shy, overweight and the butt of the cool crowd's jokes. The only bright spot in his life was his friendship with Jamie, the hottest girl in school. These two best buds were inseparable but Chris was harbouring a secret - he was hopelessly in love with her. After working up the courage to make his feelings known, a surprised Jamie tells Chris that she loves him... like a brother and an enraged Chris storms off. Ten years later, Chris has reinvented himself as a smooth talking lady-killer and when he stops by his hometown he tries to woo Jamie one last time.

Official website: http://www.justfriendsmovie.com