As his successful college comedy tour comes to an end, Pete takes a college-aged 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 takes an offer to perform at a Jewish show where Elon Gold and Modi question Pete's impulsive behaviour with a woman he met earlier that day.

Pete falls headfirst into a relationship with 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 his ex Ali staying at the comedy condo with them. Jason's misogynistic act and point of view causes Pete to question his path in comedy.

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

Pete and Kat attend a viewing party for Ali's late-night spot on Seth Meyers. 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 Town Hall, but the gig leaves him in an awkward situation.