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.