Pete has a chance encounter with famed magician Penn Jillette, who shakes his faith and inspires a questioning Pete to try living with abandon for one night.

Pete decides to spend the day with Leif, who encourages him to be open to the universe. Their carefree attitude is challenged when the two find themselves at odds and in trouble with the law.

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.

Pete tries to be supportive when a fellow comic at The Boston gets his big break. Later, he reconnects with Jess, who encourages him to find a healthy way to express himself.

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.

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.

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.

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.

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.

Pete falls headfirst into a relationship with a new girlfriend, Kat, who encourages him to be more aggressive in his career. On the night of their three-week anniversary, things amp up after a visit to a sex shop and a comedy show that morphs into a night all about Pete.

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.

During a tour stop, Pete pays a visit to his parents and introduces them to Kat, who notices the uncomfortably close relationship he has with his overbearing mom. As he tries to keep the peace, Pete grows increasingly trapped between the two most important women in his life.

Pete and Kat attend a viewing party for Ali’s late-night spot on Seth Meyers’ show. Tensions mount as Ali is nervous about how her set went and Kat becomes jealous of Pete’s friendship with his ex.

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.

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.