Demetri just can't stay away from relationships. He moves from one woman to the next, and these women aren't any real prize. Dismayed by his actions, Demetri's roommate Jake bets him that he can't stay away from commitment for six months. It's a struggle for Demetri, but he manages to comply – for a short time, at least.

Once he notices interest from a co-worker, it becomes increasingly hard for him to avoid women, just to be safe. One of his exes, a very pushy woman who pops in and out of Demetri's life, refuses to take no for an answer, causing Demetri to find some courage in order to win his bet with Jake, and not lose Corinne, the woman he has fallen in love with.