Mr. Jealousy (1998)

Synopsis
In this dark comedy, former broadcast journalist and current substitute teacher Lester Grimm (Eric Stoltz) is not especially good at displaying a healthy trust in his relationships. Ever since the age of 15, when Lester's first girlfriend ditched him for a 24-year-old, Lester has displayed an overpowering jealousy toward the women in his life -- which explains why he's still single. When Lester meets Ramona Ray (Annabella Sciorra), he's determined that this time he'll keep his emotions in check, until he learns that she has a rather checkered sexual history -- and her most recent boyfriend was a best-selling novelist, Dashiell Frank (Christopher Eigeman). Desperate to know if they still have feelings for each other, Lester starts crashing Dashiell's group therapy sessions in hopes of getting an inside scoop on what he has to say about his ex. Mr. Jealousy was written and directed by Noah Baumbach; it was his first film after his acclaimed independent debut Kicking and Screaming. ~ Mark Deming, All Movie Guide