Back in the late-80s Bill Canning was a dumpy, miserable pubescent, perpetually taunted by the object of his desire, sassy teenage schoolgirl Cherry Richardson. Today he is successful and drop-dead handsome, but remains haunted by the memory of Cherry humiliating him. Cherry is now a jaded divorcee who is desperate to get back into the dating game. Bill tracks her down to a speed dating event, where he attempts to exorcise his demons at her expense.