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 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.