Written by: Pete Holmes & Judd Apatow
Directed by: Ryan McFaul
In a dimly lit room, Pete sits in a beat up recliner, eating takeout Chinese food. Clearly at a low point, his state worsens when he opens his laptop to find a Facebook video celebrating his “friendship” with his now ex-wife, Jess. He changes gears and searches for“boobs,” then “big boobs.” As Pete turns off “safe search” and gets comfortable, Leif opens the garage door, exposing Pete in action. Leif implores him to “pull his weight” in their relationship and help pay the bills.
Pete mixes gummy bears into chocolate ice cream at his job at Cold Stone Creamery. When a satisfied customer gives Pete a tip, he and the other servers are forced to perform an embarrassing song and dance.
A young woman, Ali Reissen, walks up to Pete outside The Boston and asks for a manager. She explains she’s a comic and is looking for stage time so she can tape a set. Although she’s not “passed” at the club, Pete is intrigued and gives her a slot. After Ali’s set, Jason returns and barks at Pete to get back on his corner.
After doing a set at The Boston, Pete goes to The Village Underground where he catches up with a group of comedians all preparing to go to The Hole — a risqué burlesque joint — for Dan Naturman’s birthday. The comedians agree Pete is too square to go to a place that raunchy, so they leave him behind. After sitting alone for a minute, Penn Jillette pulls up a chair, and discusses God and the universe with Pete, shaking him.
Pete has an existential conversation with Doug Benson which gives him the nerve to argue his way into The Hole where he finds the other comics. Still shaken by his conversation with Penn Jillette, he decides to drink...a lot. As Pete parties, he becomes more carefree and even funnier. He returns to The Village Underground and joins Artie Lange and Dave Attell on stage.
At the bar after the show, Pete runs into Ali who is pissed Pete robbed her of stage time when he was goofing off with Dave and Artie. With his inhibitions lowered, Pete tells Ali she should take him home with her, and despite her initial pause, she agrees and they have sex.