Chris Brander has it all--money, good looks and a flashy job as an LA music executive. But back in high school in New Jersey in the 1990's, 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 Palamino a super-popular cheerleader. But Chris was harboring a secret--he was hopelessly in love with his best friend. On the night of their high school graduation, Chris finally works up his courage and makes his feelings known. In response, a surprised Jamie proceeds to give him the "Just Friends" speech. Enraged and humiliated, Chris declares himself no longer friends with Jamie and storms off. Ten years later, Chris has reinvented himself as a smooth talking lady-killer, living large in Los Angeles. Chris's boss, KC, has just given him his most challenging job assignment yet--turning spoiled socialite, diva and magazine pin-up girl Samantha James into a pop-singing sensation. The well-known fact that Chris and Sam used to date, and that she still carries a torch for him, makes it all the more hellish. The less than talented Sam doesn't feel she can "create" unless Chris whisks her off to Paris. En route, a plane malfunction causes them to make an unexpected pit-stop in New Jersey--the first time Chris has been back in 10 years. Chris' plans to only stay the night are detoured when he runs into Jamie working at the local bar. Suddenly faced with the chance to undo the past and "seal the deal" with the "just friends" girl of his dreams, Chris finds himself postponing Paris. This sets off a chain of events in which Chris tries to woo Jamie, all the while distracting the suspicious Samantha. Unbelievably, Chris is finding it more difficult to romance Jamie than it was 10 years ago. Can one escape the clutches of the 'friend zone?' Is it possible to go from 'just friend' to boyfriend? Chris is about to find out the hard way.