Brooklyn writer Jonathan Ames waits as his girlfriend Suzanne's stuff is loaded onto a Moishe's movers truck. After packing her things, Suzanne tells him that the reason she is breaking up with him is due to his over-drinking and pot-smoking. Jonathan tries to stop her from leaving, but to no avail. Her neighbor Ava suggests he go on Craigslist in search for a rebound partner.
Instead, Jonathan lies in bed and reads his copy of Raymond Chandler's Farewell, My Lovely. From the book, he gets the idea of advertising himself as an unlicensed private detective online. Seconds after posting the Craigslist ad, he receives a call from his best friend Ray Hueston. They hang at a café and mull over their respective relationships.
As he gets home, Ames gets a call from his first client, a 19-year old girl named Rachel, whose sister has just gone missing. Jonathan meets her at a restaurant, and they discuss the circumstances behind her sister Lisa's disappearance. His publisher George Christopher calls him reminding Ames of the event he needs to cover that evening.
At the gallery in Manhattan, George invites Jonathan to light some weed in the bathroom. Christopher tells Ames he is dying of boredom from the event, and Ames shares his to his boss about the recent break-up.
After taking some notes for his event coverage feature article, Ames heads out in search of Vincent and Lisa. His first stop is the bar where Vincent works, but he is neither there nor at home. The bartender tells him to try looking for Vincent at West Side Inn.
At the hotel, the rude and unwelcoming attendant says he has to pay even if he's just sitting in the waiting room. After waiting a long while and falling asleep, Jonathan goes back to the attendant, who, after being handed some more cash, finally discloses Vincent's room number.
He goes up and finds Lisa tied to the bed. As Vincent is about to assault him, Jonathan hides inside the bathroom and gets another call from George, who wants to have another pot session. Ames tells George that it's not a good time and hangs up. He then reveals to Vincent that he is an unlicensed private eye hired by Lisa's sister to look for her.
Vincent, who himself has been recently dumped by Lisa, talks to Jonathan about his own break-up. Having an odd understanding of Stockholm Syndrome, Vincent tells Jonathan that he tied Lisa to bed hoping she'll fall back in love with him. Police officers then arrive and take Ames to the station.
With Vincent and Lisa not pressing any charges, the police officer lets Jonathan go with a stern warning. Ames rides the subway home and again meets with Ray at Smooch café. Ray complains to Jonathan about his own issues with his girlfriend Leah. Before Jonathan can even share his recent escapade, Ray sees Leah riding her bike, so he stands up and walks away. Leah catches up to him, and Ray opens up to her. Feeling sorry for Ray, Leah hugs him by the sidewalk.
At home, Jonathan opens his email account to find another client, a woman named Jane Lessing, seeking his not-so-professional help. Ames contacts her and agrees to take on the case.