When Jonathan Ames's girlfriend Suzanne moves out (because he allegedly spends too much time drinking white wine and smoking pot), he comforts and distracts himself by reading a Raymond Chandler novel, 'Farewell, My Lovely.' Then later, in a moment of odd whimsy, partly inspired by Chandler and a glass of white wine, he posts a listing on Craigslist offering his services as an unlicensed private detective.
Looking to unburden himself and to seek counsel, Jonathan meets up with his best friend Ray who is preoccupied with his own troubles with his girlfriend Leah (a divorced, single-mother with two young children and a sluggish libido, due to the rigors of childcare). When Jonathan gets a call from a young girl looking for her missing sister, an NYU coed, he takes the case, but first he has to cover an event for his sometimes-boss George Christopher, the editor of 'Edition' magazine. George and Jonathan smoke pot in the men's room before Jonathan is able to begin working on his case in earnest. Following his one lead which brings him to a seedy hotel, Jonathan eventually pushes his way into a rent-by-the-hour room, where he finds the missing sister tied to the bed by the boyfriend she is trying to break up with. The cops show up, free the sister and take Jonathan down to the station, where he receives a strict warning not to impersonate an investigator anymore.
Back in Brooklyn, Jonathan and Ray commiserate over their rough nights. But Ray's misery once again edges out Jonathan's - until Leah shows up and she and Ray make up. Alone again, Jonathan returns home and, discovering another response to his Craigslist ad, is unable to resist the Sirens' call for help.
