It's Labor Day weekend and most of the men are sending their wives away for a few days. Don Draper's wife Betty is dreading the thought, as her father and his new girlfriend, whom she detests, will be staying with them. With the election approaching, the team at Sterling Cooper is gloomy since the Nixon campaign has not been following their advice. Roger Sterling was hoping to spend Friday night with Joan Holloway but having just seen the movie Piso de soltero (1960), she is feeling a bit used. She plans a night on the town with her old college friend who has some surprising information for her. Don and Roger invite twin sisters from a casting call to join them for a drink but things go badly for Roger who suffers a serious heart attack. After the incident Don ends up spending the night with Rachel Menken where he reveals a lot of his inner self.

Don and Betty try to keep up appearances as they go to Betty's parents after her dad has a stroke. Peter has a long-dreaded meeting with his mother before he and Kinsey leave for a convention in Los Angeles.

Don is brought in to save the day for a P.R. campaign involving the building of the new Madison Square Garden, only to have the rug pulled out from under him. At home, Betty argues with her brother over how to care for their sick father.

Roger Sterling throws an expensive party with his new wife, Joan throws a dinner party, Peggy and Paul get stoned while working on an ad campaign, and Don's daughter Sally steals money from her grandpa.

Don has reservations about a misguided potential client who wants to sell jai alai as the "new national pastime." Meanwhile, Sal produces the "Patio" television commercial, Peggy searches for a roommate, and Betty's father passes away.

Betty has hallucinations of her deceased father as she delivers her baby, Peter considers trying to sell the untapped "Negro market" to a reluctant client, and Peggy begins to question her future at Sterling Cooper.