Billy Longman 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, 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, the misogynist from Boston; Brad, the trust-fund baby who NEVER has any romance problems; and Jimmy, the struggling improvisational actor who's even more pitiful with women than Billy. Despite their best efforts, Billy's luck doesn't change much.