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 Stoltz
as Lester Grimm, aka Vince

Annabella Sciorra
as Ramona Ray

Chris Eigeman
as Dashiell Frank

Carlos Jacott
as Vince, aka Leo

Marianne Jean-Baptiste
as Lucretia

Brian Kerwin
as Stephen

John Lehr
as Lint

Peter Bogdanovich
as Dr. Howard Poke

Vincent Polidoro
as Young Lester Grimm

Yvette Brooks Grant
as Paulina