After his college comedy tour is over, Pete takes the young comedian Jaboukie under his wing. As they go to audition at The Comedy Cellar, Pete comes to realize the Jaboukie doesn't need his help, while he needs to focus more on his work.
As Pete does a gig at a synagogue, he meets a woman named Kat, who admires his talent, and they spend the day together.
As Pete and Kat spend more time together, she pushes him to follow his dreams. She convinces him to go back to The Comedy Cellar.
As Pete goes with Ali, and Jason to do shows at a club in New Jersey, they land in trouble because of Jason's misogynistic attitude. Pete decides to take a job at a Christian comedy circuit.
Pete takes Kat to meet his parents during a tour stop. As his mom begins to clash with Kat because of their different personalities, Kat notices how Pete is overly attached to his domineering mother.
Pete takes Kat to a watch party at The Comedy Cellar for Ali's act on Late Night with Seth Meyers. But people start to leave after another act steals the show. Kat thinks that Pete is cheating on her.
Pete finds himself in an awkward situation when he runs into New York comedian Jessica Kirson while he's on a Christian tour. Pete and Kat confront each other about the future of their relationship.
When Pete is selected to open for John Mulaney, things take an unexpected turn when Pete discovers that they wanted someone else and not him. Pete manages to perform well and impress Mulaney. Pete is offered a steady gig at the club.