Chris Brander (Ryan Reynolds), a former high school geek who has transformed into a successful and attractive music executive has always been in love with his best friend from high school, Jamie Palamino (Amy Smart).

During a business trip with his eccentric pop star client Samantha James (Anna Faris), Chris ends up back in his hometown where runs into Jamie and decides to finally express his feelings for her. However, things get complicated as Chris tries to navigate the challenges of moving from the "friend zone" to a romantic relationship.