Numbed after his girlfriend moves out because of his repeated failure to stop drinking and smoking pot, between-books novelist Jonathan Ames peruses his favourite Raymond Chandler novel and is inspired to place an online ad offering his unlicensed services as a PI.
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 to see if he's been unfaithful. Jonathan heads out in search of her boyfriend - with uncomfortable results.
A filmmaker and fan of Jonathan's first book is interested in having him rewrite a screenplay. Later, after leaving his personalised script in a therapist's office during an ill-advised late-night tryst, Jonathan asks Ray to pose as a patient in order to retrieve it.
Jonathan falls for his latest client, the mother of a boy whose skateboard was stolen by neighbourhood bully. Meanwhile, Ray agrees to help a lesbian couple start a new family, and George has a nostalgic "armpit crush" on a young publicist he hopes to woo.
A Russian parolee hires Jonathan to track down a chanteuse known as "the Lonely White Dove". After a vodka-fuelled reconnaissance at the restaurant where she works, Jonathan persuades Suzanne, Ray and Leah to join him there for dinner, failing to reveal his true purpose
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.
Concerned over the sudden disappearance of the two lesbians who've 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.
Having picked up the gauntlet thrown by Richard, the Edition team (George, Jonathan, Ray) gear up for a tripleheader boxing challenge against their GQ rivals, but the women in each of their lives offer some pretty compelling reasons why winning a fight isn't everything.
Jonathan is hired by a cop with a S/M fetish to infiltrate an S/M dungeon after learning it's about to be busted and his name is on their client list. Elsewhere, Ray gets some bad news and George deals with a merger.
Jonathan is hired by George's nemesis and boxing foe who is suspicious of his wife having an affair. Meanwhile, George learns he has a new female urologist and Ray plots to win back Leah by penning a comic book.
George worries about remaining 'intact' after getting some sobering news from his urologist. Jonathan's day gets worse when a pair of S/M henchmen kidnap him, demanding a ransom that calls George and Ray to action.
A professor hires Jonathan to track down a valuable item whilst George finds an alibi to explain the results of his drug test. Flushed with cash from his comic book, Ray heads to the bar and meets a familiar barfly.
Jonathan tries to repair the relationship between a limousine driver and his wife. Elsewhere, Ray has a meeting with Kevin Bacon.
Leah hires Jonathan to help find her new dog "Little Ray". Ray joins in the search, getting some inside help from a local woman. Elsewhere, 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, so 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.
Jonathan marks the release of his new book but must process some alarming family news before trailing a mysterious woman on another case. George is reunited with his daughter, and Ray spends a day with his biological son.
On the run from the police, Jonathan and Ray turn to Howard for help with trying to find out who framed Jonathan for murder, while George runs interference for them in his own inimitable, marijuana-induced way.
Jonathan is thrown for a loop when another scheduled guest on "The New Dick Cavett Show" happens to be his nemesis. Meanwhile, Ray's attentiveness as a father is tested and George is floored by Emily's latest news.
George urges Jonathan to show Emily what it's like to be out with a younger man but they wind up on a stakeout with a wannabe gumshoe. George goes out on the town with Bernard while Ray is drawn to an older woman.
Jonathan and George try counselling but Jonathan thinks he might have more luck investigating a rival's business practices. George signs up for singing lessons and Ray finds himself with an embarrassment of romantic riches.
George and Ray tag along when Jonathan is hired by an old college flame and her father to guard the family's wedding jewels. Meanwhile, the bursting of Ray's romantic bubble forces him to move in with George.
Jonathan pursues new leads on his paternity case with Rose. Meanwhile, George and Ray try to make amends for their particular transgressions.
George celebrates Emily and Bernard's wedding while Ray is comforted by his son Spencer. Jonathan considers breaking up with his new girlfriend, but when he's kidnapped, an army of Super Ray fans spring into action.