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.

A smitten Russian parolee contracts Jonathan to track down a chanteuse known as "the Lonely White Dove." After a vodka fueled reconnaissance mission at the Brighton Beach restaurant where the singer works, Jonathan persuades Suzanne - along with Ray and Leah - to join him there for dinner the next night, without revealing his true purpose. Meanwhile, George decides to get in touch with his feminine side as a way to drive sales of his sagging magazines.