The series begins with Jonathan Ames, a novelist, who is stuck writing his second novel. He is outside his New York apartment arguing with his ex-girlfriend, Suzanne. She told him for months that if he was serious about their relationship, he would have stopped smoking pot and drinking alcohol, but he never did. Alone in his apartment,  he stumbles upon a private detective novel, Farewell My Darling, and is inspired to put up an ad on Craigslist as an (unlicensed) private detective.

His first case is a call from a 19 year-old woman named Rachel whose sister has been missing for a couple of days.  Jonathan meets with Rachel at a coffee shop to collect more information about her sister. Rachel doesn’t seem too impressed with Jonathan’s detective skills, but nonetheless agrees to hire him.

Shortly after, Jonathan gets a call about an event which is that night. His boss, George, insists that he must go.  The event is just another boring ritzy event that George throws. Right when Jonathan gets there George ushers him to the men’s room to smoke some pot. You realize right away that George is really “bored to death” and finds something very intriguing with Jonathan’s youth.

Jonathan leaves the party early on a mission to find Rachel’s sister. He gets a tip from a bartender that Vincent, Rachel’s sisters’ boyfriend, called in sick and is staying at a local motel. Jonathan rushes over to this motel only to spend countless hours and dollars waiting in the front lobby. The jerk at the front desk finally agrees to work with him (for a price) and informs him  which room Vincent is staying in.

Being like the heroic character he imagines, Jonathan pounds on the door, pushes his way into the room, and then barricades himself in the bathroom. All does not go as planned. Somehow he forms a bond with Vincent over the tragedy of breakup and ends up offering him a peace pipe – his one hitter. Just as they start to get high, there is a knock on the door – the real police were dispatched due to a call-in about loud arguing.  They end up taking Jonathan in for questioning and let him go with a condition to take down the ad and to stop pretending he’s a real private eye.

The episode ends with Jonathan alone in his apartment, deciding to answer another woman’s plea for help.