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 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.
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.