After his first date at age 15 ended with the girl making out with another man at a party, aspiring writer Lester Grimm has treated all his girlfriends with jealousy and suspicion. While dating Ramona Ray, paranoia gets the best of him when he discovers that her most recent ex is successful novelist Dashiell Frank. Lester begins attending the same group therapy sessions as Dashiell to learn about Ramona's past with him.

Eric Stoltzas Lester Grimm, aka Vince
Annabella Sciorraas Ramona Ray
Chris Eigemanas Dashiell Frank
Carlos Jacottas Vince, aka Leo
Marianne Jean-Baptisteas Lucretia
Brian Kerwinas Stephen
John Lehras Lint
Peter Bogdanovichas Dr. Howard Poke