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.

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.