In the first segment, Louie volunteers to chaperon his daughter's field trip along with her teacher, which a surly bus driver helps turn into a disaster. In the second segment, Louie goes on an awkward and unsuccessful first date.

In the first segment, the conversation during a poker game becomes an intense exploration of gay culture. In the second segment, after Louie's brother depresses him about the finality of his divorce, Louie reminisces about a high school crush, subsequently looking her up on Facebook.

In the first segment, Louie goes to a doctor who's an old high school friend with an odd sense of humor. In the second segment, after performing at the Comedy Cellar, he dines with a fellow comedian who harbors passionate political views.

In the first segment, Louie hooks up with a young woman at the Comedy Cellar (Elizabeth Hower) who's attracted to older guys. In the second segment, he bonds with a woman he meets at a PTA meeting while their kids are on a play date. Throughout the episode, Louie has odd interactions with his therapist.

Louie endures a number of typical airline problems traveling to Birmingham for a gig. After the show, he meets an intense fan and her intimidating brother at a local diner, and a sheriff who just wants a little appreciation.

In the first segment, Louie deals with a heckler during his gig at the Comedy Cellar. In the second segment, Louie is guilted into accepting a role as a cop in a movie directed by Matthew Broderick, but finds acting difficult.

In the first segment, Louie deals with the awkward situation created when he's propositioned by his brother to join in a three-way. In the second segment, Louie's unpleasant and stupid mother visits to report that she's now a lesbian, but is met with unloving indifference from Louie and injured resentment from Robby.

After leaving his girls with their mother for a week, Louie tries to cope with their absence. He initially plans on exercising, but ends up eating ice cream and pizza for two days. Later, he's pressured into smoking pot with his obnoxious neighbor and decides to get an adult dog, which promptly dies. After Animal Control picks up the dog to dispose of it, Louie's girls return and he tells them he had a good weekend.

Flashbacks depict Louis learning about sex as a boy from his father and in school. On a date, he is emasculated by a high school student who threatens to beat him up. He secretly follows the bully home to Staten Island and confronts his parents.

Louie tries to overcome his fear of dentists, and tries to get a date with an African American grocery cashier.

When a nun at his Catholic school feels a young Louie and his friend aren't sufficiently penitent over Christ's suffering on the cross, a visiting doctor is brought in to give a graphic, medically specific description of the event, which haunts and frightens Louie. But Louie's mother turns up in a new incarnation as a wise and loving parent who tells Louie that relying on dogma isn't the best way to be a good person.

After an exhausting morning getting his girls ready for school, Louie lets a fellow dad at his daughter's school train him at the gym, where he proves to be in worse shape than he thought.