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.

As Jonathan tries to mend his relationship with Suzanne, another case falls onto his lap. This time, he is tasked by a woman named Jennifer to gather proof of her boyfriend Gary's infidelity. Jonathan, who learns his new client loves to drink as much as he does, tracks down Gary and stumbles upon an unsatisfying outcome.

While attending a New York film society function, George introduces Jonathan to a filmmaker, who asks him to rewrite a screenplay. Later, he goes out with a party girl and leaves the script at her home, which happens to be a shrink's office. Jonathan asks Ray to pose as a patient to recover the script. Meanwhile, George encounters his ex-wife and her smug new husband.

Jonathan is hired to reclaim a kid's stolen skateboard from the neighborhood bully while Ray helps out a lesbian couple who wants to start a new family. George tries to woo a young publicist at the opening of a new restaurant in Brooklyn.

A recently-paroled Russian enlists the services of Jonathan to search for the object of his infatuation, a songstress known only as "The Lonely White Dove." He checks out the bar where she sings and convinces Suzanne, Ray, and Leah to have dinner there the following night without revealing his primary intention. George gets in touch with his feminine side to boost his magazines' dipping sales.

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 Jonathan's neck before the woman's enraged brother breaks it?

Concerned over the sudden disappearance of the two lesbians who have been buying his sperm, Ray enlists Jonathan to help him track the couple down. After breaking into their apartment, Jonathan learns the pair has flown the coop--but not without leaving behind a clue that both shocks and intrigues Ray. Meanwhile, George ignores Jonathan's warnings by publishing a disparaging editorial about Richard Antrem (Oliver Platt), sending his publishing rival into a fit of rage at the local watering hole.