

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.
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Brian Kerwin
Stephen

John Lehr
Lint

Peter Bogdanovich
Dr. Howard Poke
Vincent Polidoro
Young Lester Grimm
Yvette Brooks Grant
Paulina

Jose Soto
Club Promoter

Delaine Yates
Ariana

Nico Baumbach
Ex-Boyfriend
Joel Kastelberg
Curt

Dean Wareham
Music Video Director

Leigh Zimmerman
Lois
Patricia Towers
Museum Woman

Helen Hanft
Millie
Andrew Mills
Trey
James P. Engel
Harold

Martha Gehman
Josselyn

Lauren Katz
Maria
Michelle Blakely
Imogen
Matthew Kaplan
Omar