The Agency is looking to land an advertising contract to promote tourism to Israel. Don and his team try to come up with a theme but know so little about the country that they're stumped. So Don calls Rachel Menken to see if she has any ideas. Roger Sterling is getting tired of sneaking around with Joan Holloway and suggests she should get her own apartment but she knows better. Peggy comes up with an advertising concept during a testing session for a new line of lipsticks and she's subsequently asked to write copy.

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.

Freddy and Ken take a client out to lunch who stirs Roger Sterling's heart.

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.

On the weekend of the John F. Kennedy assassination, Pete finds out that he lost the promotion to Cosgrove, Roger Sterling's daughter's wedding goes off as planned, and Betty musters up the courage to respond to Don's confessions.

Don and Megan take a trip to Hawaii for the holidays, Sally's friend visits the Francis family, a comedian torpedoes Peggy's Super Bowl ad campaign, and Roger gets some bad news about his mother.

Don strikes up a friendship with the surgeon in his building, Peggy tries to save her campaign, Roger makes a scene at his mother's funeral, and Betty goes to Manhattan to find Sally's friend.

Peggy becomes unsatisfied with her apartment and with Abe, Don has an eventful weekend with Betty while Megan has problems on the set, Roger has time with his grandson, and Pete begins exploring his options outside the firm.

With his personal and professional life crumbling around him, Don positions himself for a change of scenery. Meanwhile, Pete's life is falling apart as well, thanks to the meddling of Bob Benson.

Don is on the outside looking in on the forced indefinite paid leave from his job. While Ted heads back to New York for a few days, Don takes the opportunity to head to Los Angeles in part to meet with a California transformed Pete while he reunites with Megan, who is living full time there while pursuing what looks to be a promising acting career. Back in New York, Peggy avoids Ted at all cost while she learns to deal with the new "Don", Lou Avery, most specifically on the Accutron account for which she is getting consulting help from Freddie Rumsen. On top of that, she is also having to deal with being a landlady to who she believes are overly demanding tenants. Ken feeling overworked leads to Joan taking over his scheduled business meeting with Wayne Barnes, the new Head of Marketing for Butler Footwear. Barnes' news results in Joan taking what she hopes will be seen as decisive and preemptive action in overcoming a potential problem, action which she hopes demonstrates that she deserves to be more than just a glorified secretary. And Roger meets with Margaret on her request, the two who have been somewhat estranged over the last few months. Their individual new approaches to life may result in a friction-free reunion.

Don returns to work, but quickly falls off the wagon after learning that he's been assigned to Peggy. Meanwhile, Roger and his ex-wife go to a commune to rescue their daughter, who has abandoned her child.