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.

Jonathan is enlisted to retrieve a sex tape that a female escort is using to extort money from a married New Jersey man. With Ray and George in tow, Jonathan ends up in a motel room with the escort, who attempts to blackmail him as well. Can the very stoned Ray and George save Jonathanʼs neck before the womanʼs enraged brother breaks it?