In high school Chris Brander (Ryan Reynolds) was sweet, fat and just friends with the girl of his dreams. Ten years later, he’s a successful and good-looking music executive whose past rejection has turned him into an arrogant womaniser. When he gets stranded in his hometown with his latest signing – IT girl / pop sensation Samantha James (Anna Faris) he meets up with his high school crush, Jamie Palamino (Amy Smart) and discovers his feelings for her are as fresh as ever. With stiff competition in the form of a reinvented Dusty Dinkleman (Chris Klein) – another member of his high school’s loser group – will Chris finally be able to move his relationship out of the friend-zone?