Louie's pregnant sister visits, and she needs to be taken to the hospital during the night as she is in pain. Upon hearing his sister screaming, Louie's two neighbors arrive. After some indecision, one of them looks after the kids while Louie and the other neighbor bring his sister to the hospital. Though it turns out to be a false alarm, Louie finds a bond with the people who live around him.

In the first part of the episode, Louie awkwardly scores a "non-date" with a young woman who has no real interest in him, but a shocking and unhappy encounter on his way to meet her for a movie leads to a darker, more introspective Louie that appeals to her-until he tells her the specifics of that encounter. In the second part, Louie is approached by his daughter's classmate's mom to have an emotionless sexual encounter; he agrees to do it, and comes to regret that decision every step of the way.

After a comment by his daughter, Louie has misgivings about continuing to stay in the apartment they lived in when he was married and begins house hunting. After seeing several disastrous apartments, he finds the ideal place. Despite his accountant's assurances and his own awareness that it is very much out of his price range, Louie remains committed to the idea of buying it. In the end, he repaints his old apartment with his daughters by his side.

After a disappointing experience trying to do a set at a casino lounge, Louie cancels his contract and wanders the casino floor. He ends up watching a section of Joan Rivers's set in the casino's theater, and goes backstage to meet her. She invites him to hang out in her suite, where she proceeds to explain how he should be grateful for his opportunities. As a result, they have sexual intercourse and Louie goes and gets his job back.

Louie and his daughters take a long drive to visit Louie's great aunt Ellen out in rural Pennsylvania, where Louie mostly ignores his younger daughters' complaints of boredom and has a blast rocking out to "Who Are You-. There, they find her actions and vocabulary weird, specifically her use of the word nigger, referring to Brazil nuts as niggertoes. Louie decides he wants his daughters to talk to Ellen without any censoring, but the point becomes moot when she collapses and dies in her kitchen. Louie then does a stand-up bit about Tom Sawyer being a good kid and Huckleberry Finn a bigoted little jerk.

Louie starts his evening with a surreal trip on the NYC subway, where he witnesses a busker playing beautiful violin music while a filthy homeless man scrubs himself down with bottled water nearby, has a black-and-white vision of himself saving the riders from a soda-soaked seat, and then heads into the opening credits. Later, he meets his friend Pamela for lunch, and he ends up passionately telling her how he feels about her. And she doesn't respond at first, leaving him to misread a later invitation of hers, and the revelation ends with Louie standing outside her building and screaming in pain and anger.

The episode begins in a flashback with Louie filming the pilot for a sitcom. After complaining about the unrealistic dialogue and use of Bob Saget as the next door neighbor, Louie is shown arriving home to an unseen and presumably upset wife and their newborn baby Lilly. The episode then jumps to Lilly's tenth birthday. Louie sets out to obtain Lady GaGa concert tickets as a birthday present for his daughter, but doing so means he has to approach Dane Cook, a very successful comedian who is upset by accusations he has stolen material from Louie.

The spokeswoman for a group called Christians Against Masturbation, Ellen Farber, and Louie have a debate about the morality of masturbation on a the FOX News program, Red Eye w/Greg Gutfeld. Louie is the only person they could find willing to openly defend masturbation. After the show Louie goes home and masturbates while imagining a woman he had just seen on the elevator. Then, at Ellen's request, he attends a CAM meeting, and goes out for drinks with her after. She invites him up to her suite, but Louie is denied when he tries to go in for a kiss. Ellen gives a long passionate speech about how nice it would be to talk, date a long time before a kiss (but not "making out"), then finally getting to see her in her underwear on their wedding night. Then he goes to her suite bathroom to masturbate.

After a set, Louie is greeted by Eddie Mack, a fellow comedian who started his career the same time as Louie but has never found much success and lives in his broken-down car. He and Eddie catch up after not seeing each other for 20 years by going to the liquor store and then an open mic where Eddie does a very funny routine under the stage name "Shitty Fat Tits" before Eddie confesses his plans to end his own life, leaving Louie to ponder how (or if) to dissuade him.

Louie and his daughters go trick-or-treating on Halloween in New York City. As darkness falls, they are confronted by a pair of costumed punks. Louie's younger daughter Jane confronts the two men and helps scare them away. In the second part of this episode, Louie sits in on a brainstorming session for an upcoming cop movie. Louie's ideas for the script get the attention of a high-powered movie producer named Ellie. Louie is promptly invited to lunch to discuss movie ideas, but ultimately his ideas prove too dark for Hollywood.

Louie unwillingly takes home Jane's class ducklings for the evening. The next morning he embarks on a 5-day USO tour in the Middle East, when unbeknownst to him, Lily had hidden one of the ducklings in his suitcase to keep him safe. Louie meets other entertainers (including country western singer Keni Thomas) as well as many various soldiers during his time overseas. The duckling ends up bringing Louie and others good luck in ridiculous and heartwarming fashion.

Louie waits at Grand Central Station to pick up his sister and niece for a visit. However, his sister surprises him by dumping the niece Amy on him and running off to catch a train to Philadelphia. Louie and Amy spend the night in New York together, visiting an indie rock club at her request, after which she asks to see Louie perform. After seeing her enamored with Godfrey's set, Louie attempts, unsuccessfully, to impress his niece by doing crowd work. After the set, Louie is surprised to see Godfrey spark up a lively conversation with the usually sullen teen. When they arrive back at the apartment, Louie receives a call from a Philadelphia hospital informing him that Amy's mother was found "acting irrationally" in a public fountain and that she is being held under observation. With Amy's father out of the picture, Louie volunteers to keep Amy until his sister is released.

Louie takes some bad advice from Steven Wright and winds up getting in a car with an attractive but somewhat creepy woman who takes him to New Jersey for a devil's three-way with her husband, which leads to Louie wandering the Jersey 'burbs at night and relying on his pal Chris Rock to rescue him;
Louie takes a trip to the airport with Pamela.