Mr. Jealousy (1998)

Lester Grimm, a young writer, suffers a painful first date at 15, leaving him with lasting emotional scars. This experience fuels intense jealousy and suspicion in all his relationships. His current girlfriend, Ramona Ray, triggers these feelings when he learns about her past with the famous author Dashiell Frank. Unable to cope with his insecurities, Lester joins Dashiell's group therapy sessions, determined to uncover the truth about Ramona's history and manage his own emotional turmoil.