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.

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.

Pete reunites with Ali, who introduces him to New York's alternative comedy scene over the course of one night.

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.

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 spends the day with Leif while continuing to grapple with his beliefs.

A chance encounter with Penn Jillette rocks Pete's world and leads to a wild night.