
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.

as Lester Grimm, aka Vince

as Ramona Ray

as Dashiell Frank

as Vince, aka Leo

as Lucretia

as Stephen

as Lint

as Dr. Howard Poke

as Young Lester Grimm

as Paulina

as Club Promoter

as Ariana

as Ex-Boyfriend

as Curt

as Music Video Director

as Lois

as Museum Woman

as Millie

as Trey

as Harold

as Josselyn

as Maria

as Imogen

as Omar

as Marlon

as Amy

as Arliss

as Nat

as Irene

as Waitress

as Male Classmate