Broken up after his breakup with his girlfriend Suzanne, Jonathan Ames reads through Farewell My Lovely, his favorite book by Raymond Chandler. Enlivened by the novel, Ames places an online advertisement as an unlicensed private investigator. His first unwitting client who seeks his services is a 19-year-old girl looking for her missing sister.

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.