Bored to Death Episode 1.06 The Case of the Beautiful Blackmailer

Jonathan meets with Mr. Eaton in a diner in New Jersey about a possible case: The married father of two had a tryst with a woman, Sophia, he found on Craigslist who claimed she was also married, but who turned out to be a blackmailer. Sophia has demanded cash payments in exchange for not showing the video of their liaison to Mr. Eaton's wife. Mr. Eaton needs Jonathan to get the tape back.

Jonathan sets up his own meeting with Sophia at a New Jersey motor lodge in order to entrap her. Stopping by Edition magazine on his way to the sting, Jonathan cannot hide his secret life from George any longer. He reveals he's been moonlighting as a private detective and tells him about his current case. George wants to go along, insisting it would make a great cover story. George and Ray meet for the first time (Ray is driving the getaway Subaru) and they stop off at a spy store on their way to New Jersey and stock up on equipment.

At the motor lodge, Jonathan gets a call from Sophia and is ordered to rent a room. Nervous, he realizes he has to take his undercover tactics all the way. While waiting in the Subaru, George and Ray get stoned and George admires Ray's rejected Esquire cartoon chronicling his sperm donation. When Sophia learns Jonathan is scamming her, she turns the tables, threatening to expose him on the Internet if he doesn't pay up. Her partner in crime, Carl, shows up with a taser and escorts Jonathan to the ATM outside. George and Ray are too high to notice and Jonathan must rouse them to track Sophia and Carl to her suburban home.

When Carl leaves, Jonathan confronts Sophia to get the tapes (he's certain she likes him because she had two orgasms during their encounter). She begs him not to call the cops, as she's only doing this to help Carl (her brother) escape gambling debts with the wrong kind of people. Just then, Carl returns and Ray and George have to rescue Jonathan, armed only with a snowscraper and a toy unicorn, Janet. As they speed off, they run straight into a police car. While this helps them elude Carl, it creates other troubles. But as the sun rises in New Jersey, George promises to make any criminal charges go away, and to provide the funds to fix Leah's car by hiring Jonathan and Ray to do a comic about the case of the beautiful blackmailer.