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Pete jumps at the opportunity of a lifetime to open for John Mulaney at New York’s Town Hall, but the gig leaves him in an awkward situation.

In an attempt to show Ali that he has a backbone, Pete enters a comedy-roast battle, but finds that being mean is harder than he thought. The fierce competition brings uncomfortable truths to the surface, forcing Pete to examine his priorities in life.

Pete reunites with Ali, who takes him on a tour of New York’s alternative comedy scene, where they encounter a wide array of comedians and venues over the course of one night.

On a trip to a comedy conference to book college gigs, Pete and Ali clash over the best strategy to appeal to the college crowd.

Pete’s decision to organize a secret benefit for an ailing comedy vet finds him scrambling to put on a good show and facing hard truths about Artie.

When Pete is abandoned by Artie, he is rescued by comedian Bill Burr, who takes pity on him and offers his guest room. As they become unlikely friends, Bill encourages Pete to toughen up and embrace his masculine side.

Feeling like his time away from New York has taken him out of the scene, Pete accepts an offer to perform at a Jewish show, where Elon Gold and Modi question his impulsive behavior with a woman he met earlier that day.

Aspiring comedian Pete finds himself without a home after he catches his wife, Jessica, in a compromising position. As Pete attempts to find solace at a New York comedy club, he befriends cynical comedy legend Artie Lange, who reluctantly offers him some pizza, some advice and a couch.

While staying at T.J. Miller’s place, Pete has the unsettling experience of witnessing a comic who can’t “turn it off.” Hearing from his wife, Jessica, Pete and T.J. travel upstate to her yard sale, where Pete unexpectedly teams up with Jess’ new boyfriend, Leif, to get back a prized possession. After Jess voices her true feelings to Pete, the sale comes to a dramatic end.

When Pete’s parents decide to come to New York for his mother’s birthday, Pete begs Jess to come along and keep up the charade of their marriage, but an incredibly tense dinner reveals harsh truths about their relationships, as Jess struggles to keep quiet. Pete faces a turning point.

Pete wallows in his new reality, but Artie Lange snaps him out of it with an offer: In exchange for a ride to Albany, Pete can be Artie’s opening act. Pete meets co-headliner T.J. Miller and attempts to save Artie from breaking his sobriety by getting between him and the temptations of an ardent fan.

While enjoying the perks of being on a Christian comedy tour, Pete feels busted when he runs into NY Cellar comic Jessica Kirson in Charleston. After ghosting Kat while on the road, Pete finally sits down to talk about their relationship.

As his successful two-month college comedy tour comes to an end, Pete, donning a new look and confidence to match, takes a college-age aspiring comedian, Jaboukie, under his wing. But Pete's return to New York finds him having an awkward reunion and a big audition at the Comedy Cellar that could change everything.

Pete travels to New Jersey with Jason to do a weekend of shows at a big corporate comedy club and is surprised to find Ali, his ex, staying with them at the comedy condo. Jason’s misogynistic act and point of view cause Pete to question his path in comedy.