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.

Having picked up the gauntlet thrown down by Richard – and having thwarted a blackmail bid aimed at getting Jonathan to take a dive – the Edition team gear up for a tripleheader boxing challenge against their GQ rivals. But with the bouts only hours away, the women in their lives offer some compelling reasons why winning isn’t everything.

Jonathan is hired by a police officer to erase the hard drive of an S&M club computer to prevent potentially embarrassing information from coming out as the officer has received word that the club is about to be raided. Leah breaks it off with Ray. George is asked to cut back on expensive meals to prevent the Magazine from going under.

Jonathan is hired by Richard Antrem, George's nemesis and boxing foe, to investigate Richard's suspicions that his wife Priscilla, George's ex, is having an affair. Jonathan's insecurities resurface when Stella announces she's not over her first love. George has a new female urologist; Ray plots to win back Leah by penning a comic book.

George worries about remaining “intact” after getting some sobering news from his new urologist, Dr. Kenwood. A bad day for Jonathan gets worse when a pair of S&M henchmen kidnap him. They demand a ransom which calls “GI” George & Ray to action.

A professor hires Jonathan to track down a valuable item. George finds an alibi to explain the results of his drug test. Flushed with cash from his “Super Ray” comic book, Ray heads to the bar – and meets a familiar barfly.

Jonathan attempts to repair the relationship between a poet/limousine driver and his wife. Ray has a meeting with Kevin Bacon.

Leah hires Jonathan to help find her new dog, “Little Ray.” Ray joins Jonathan in the search for the dog, getting some inside help. A reflective George heads to the hospital for surgery.

A dermatologist enlists Jonathan to deliver a letter to his intended at an Asian health spa. Jonathan takes Ray to the spa for his birthday, with George and his new chauffeur Vikram in tow.

A mad stalker imperils Ray on the eve of the Brooklyn Comic Con. With the help of Officer Drake, he and Jonathan piece together leads to track down the perp. George decides to make a stand at work. Jonathan has another battle with his nemesis, Louis Greene.