Bored to Death

During an unsuccessful attempt to win back Suzanne, Jonathan gets a phone call and a new case: a woman named Jennifer (Kristen Wiig) wants him to tail her boyfriend Gary (Peter Hermann) to see if he's been unfaithful. After learning that he and Jennifer share a common pastime (drinking), Jonathan heads out 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 in which Jonathan will 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 turns to 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 neighborhood bully. Meanwhile, Ray agrees to help a lesbian couple start a new family, to wife Leah's 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 she works, Jonathan persuades Suzanne--and Ray and Leah--to join him there for dinner the next night, failing to reveal 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 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 Jonathan's neck before the woman's enraged brother breaks it?