During an unsuccessful attempt to win back Suzanne, Jonathan gets a phone call and a new case: A woman named Jennifer wants him to tail her boyfriend Gary to see if heʼs been unfaithful. After learning that he and Jennifer share a common pastime - drinking - Jonathan goes in search of her boyfriend, with uncomfortable results. Meanwhile, Ray brings Jonathan along to his colonic for moral support, and George hatches a knockout plan for Jonathan to help him cover up an unsightly sore before a big speech.

At a New York film society party, George introduces Jonathan to filmmaker Jim Jarmusch, a fan of Jonathan's first book, who is interested in having him rewrite a screenplay. Later, after leaving his personalized script in a therapist's office during an ill advised late night tryst with a very young party girl, Jonathan convinces Ray to pose as a patient in order to retrieve it. Meanwhile, George is flummoxed when he runs into his sexy ex-wife Priscilla and her arrogant new husband, fellow publishing magnate Richard Antrem.

Jonathan falls for his latest client, the mother of a boy whose skateboard was stolen by a neighborhood bully. Meanwhile, Ray agrees to help a lesbian couple start a new family, to his wife Leahʼs chagrin, and George has a nostalgic "armpit crush" on a young publicist he hopes to woo at the opening of a new Brooklyn restaurant.