At first, I thought this episode was pretty depressing. But upon reflection, it really was a powerful look at women and their multifaceted roles and relationships with men.
Peggy's relationship with her boyfriend starts the episode with him stating (indirectly) that she is the alpha male and he complains about this, as it violates the traditional roles of the sexes. When the pitch to Heinz goes awry, she leaves work to go to a movie, gets high with a stranger and has anonymous sex with him. But the sex act is her way of re-gaining her dominance in her world with men and she becomes the sexual aggressor by refusing to be submissive.
During the pitch to Heinz ("Home is where the Heinz Is" (where product replaces the human heart), Peggy tells the executive the "truth" that they don't know what he wants, that he knows but won't tell them, and just wants to complain. The executive in response, compares her to a daughter figure, that he dismisses by having her fired from the account. Peggy is not treated as a associate or on equal status as the men, which is echoed by Sally's phone call to Don to complain that she is treated like a second class citizen.
There is also the powerful underlying theme of motherhood that runs through this episode. Ginsburg was born in a concentration camp and reared in an orphanage. This is told to Peggy, the unwed mother, who gave up her baby at birth.
Roger goes to the dinner party with his wife and takes LSD with Prof Tim Leary. This sequence is about "truth and lies". What better person than Roger, who works on Madison Ave and deals with illusion, to appreciate the effects of the drug and welcome the ability to talk truthfully with his wife about their failed relationship. Roger sees himself both young and old and his relationship with his wife more father / daughter. When they finally break up, she says "you never liked me." His response, "I use to." Love was never part of the marriage.
There is also a reference to the 1919 World Series, which was the famous baseball gambling scandal that showed the frailty of men and broke the illusion of baseball as a "pure" sport. The mother theme is also echoed with the woman therapist, who advises the wife/ daughter in her relationship with Roger.
Don and Megan's road trip, dominated by the color orange (sherbet, her dress, Howard Johnson) is a disaster, echoing Peggy's pitch to Heinz. Megan tells Don what he doesn't want to hear: that she has multiple roles: a job with responsibilities to her co-workers, to him as a husband. However, he only lets her have these roles at his convenience. She chafes at being the submissive partner and wants to be an equal, which he doesn't allow her to be. The trigger is when she tells Don to call his mother (last episode we find that he was reared in a brothel and his mother a whore), which sets him off and he leaves her stranded at the motel. Don, being the petulant child, regret his decision to leave his wife (mother), and tries to find her without success, even calling Megan's mother. Driving home, he remembers a prior trip in the car with Sally and the kids in the back seat, and he tells Sally that they are going to their new home. When Don reaches home his finds Megan, they fight, and Don ends on his knees with his head on her womb, declares that he thought that he had lost her. She, reluctantly, assumes the mother role and comforts him.
The episode ends with Sterling, with a drawing of a woman in lingerie crossed out that has written on it "Do Over", tells Don that the firm is having problems because he's been on a love leave. Don by himself in the empty conference room, contemplates the future.
Rich and dense stuff.
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