Jerry Falk (Biggs), an aspiring writer living in New York City, has a girlfriend, Brooke (Strickland). He falls in love with Amanda (Ricci) and has an affair with her. Amanda leaves her own boyfriend for Jerry. Brooke finally figures it out and leaves Jerry. Jerry turns to an aging, struggling artist (Allen) who acts as his mentor, which includes trying to help sort out Jerry’s romantic life. Dobel tries to convince Jerry that his manager is only holding him back and his relationship with Amanda is the most destructive force in his life. Amanda continuously cheats on Jerry. Jerry's neuroses start to worsen. Eventually Jerry leaves town as Dobel gets him a job writing for television in California. Amanda has an affair with the doctor who was treating her and runs off with him.