John gets a job writing comedy for demanding and infantile game show host Lou Cannon, which turns out to be less glamourous than expected. Meanwhile John's roommate, Jane, attempts to prove to an ex that she isn't "psycho"; and his other roommate, Motif, struggles to write a joke with a hugger punchline.

When John starts dating a doula, he faces his fear of childbirth; John talks to Lou about his provocative behavior.

When John uses his late neighbor Lapidus' jokes for Lou's monologue, he finds himself willing to rob the man's grave to get more of his material and prove his worth at work.

Mulaney doesn't understand why Jane doesn't get along with any of his dates. Lou asks John to help plan a dignified passing.

John receives a visit from his devoutly Catholic parents. Jane begins to take a certain medication to impress a guy, despite suffering some unpleasant side effects.

When Jane starts dating a marine, John and Motif, feeling guilty for their lack of service, try to sign up for a USO Comedy Tour. Meanwhile, Lou recounts how war - and improv - are hell.

When Motif learns John and Jane are not adding him to the apartment lease, he leans on his three girlfriends for support. Lou's audience plant demands a contract.

John's resentment of actor Macaulay Culkin dampens his Christmas spirit. Meanwhile, Lou is worried when his rival, network host Jesse Tyler Munoz, announces a competing holiday special, and Andre is mistaken for a puppet.

John quickly regrets mixing his home and work lives when Jane becomes Lou's new personal trainer. Meanwhile, Motif turns to Oscar for advice on his stand-up routine.

John faces the dilemma of being mean about Lou when he is invited to participate in a celebrity roast. Meanwhile, Oscar teaches Jane how to be more ladylike.

John takes Lou's advice about how to gain the upper hand with his roommates. Meanwhile, Motif shows Jane how to get her new cat to like her.

John puts his theories about teenagers to the test when he tries to impart his wisdom to his new girlfriend's 13-year-old daughter. Meanwhile, Jane and Motif become Lou's lunch companions.

When their building is infested with bed bugs, Mulaney and the gang secretly crash at a Lou's vacant pad and unknowingly eat some special Oscar "treats", leading to more problems when Lou unexpectedly returns from vacation early.