Billy Longman (Johnny Clark) is not a loser, it's just that he doesn't have much experience with the opposite sex. After all, most of the girls in college weren't interested in dating a sixteen year-old child prodigy. Even after college, Billy never seemed to find the right girl for him. All of that changed when Billy met Karen (Amy Jo Johnson), a beautiful young medical student. Unfortunately, Billy takes two years to find the right moment to tell Karen how he feels. When he finally does, he's crushed to learn that she doesn't feel the same way about him. Broken-hearted, Billy looks for 'help' from his three best friends; Kevin (Bob Marley), the misogynist from Boston; Brad (Jason Shaw), the trust-fund baby who NEVER has any romance problems; and Jimmy (John McDermott), the struggling improvisational actor who's even more pitiful with women than Billy. Despite their best efforts, Billy's luck doesn't change much. Things get even worse when dorky Jimmy stumbles upon Mae (Elisa Donovan), the love of his life, leaving Billy to face the world of dating with only Kevin and Brad as his guides. Will Brad and Kevin convince Billy to forgo his ideals and join them as frequent patrons of the 'Liars Club?' Or will Billy follow his heart and find a new way to win Karen's love?