From the very moment we meet him, Don Draper is cheating on his wife. In fact, on Mad Men, just about everyone cheats on their spouses at some point, sometimes out of emotional desperation, sometimes out of the desire to be cruel, sometimes out of lust, and sometimes out of actual love. But many of these romances — like many things on Mad Men, in general — seem plagued by an ambient sense of tragedy, either present or impending. Cheating: It’s sort of exciting, but also a huge bummer.
Betty’s whole world was ending, and it seemed like the actual whole world was ending, too — what with the Cuban Missle Crisis terrifying the country. An anonymous roll in the hay (well, on a couch at a bar) that has the added bonus of getting back at your philandering husband? A bummer, maybe, but not a tragic affair for the ages.
Happy marriages are rare in the Mad Men universe, but Harry seemed to actually have one — until he messed it up by sleeping with Hildy, the secretary. Harry and his wife seemed to have reconciled, but the horror and shame that overwhelm him when he tears up during Don’s slide projector pitch in “The Wheel” show that every once in a while, cheating can really catch up with you.
Just a few weeks after barfing all over the Sterling Cooper foyer, Roger was back to his womanizing antics, this time sweating and panting all over a tender, sweet young thing until he collapses from a heart attack. The overwhelming patheticness of the whole situation foreshadows Roger’s entire post-Mona life: grasping and gasping for the vanishing promises of youth.
We never actually see Lane and his Playboy Bunny, Toni, break up, but once Lane’s elderly father whapped him with a cane, it seemed like the romance was on its way out. Poor Lane. Poor Toni.
Bohemian Midge was mistress numero uno at the start of the series, and her relationship with Don illuminated just how broken Don and Betty’s marriage really was. Midge’s artsiness and beatnik pals held a certain appeal, though her eventual descent into heroin addiction made everything that much more tragic. The real misery of Don and Midge’s relationship was just how easy it seemed for Don, how seamlessly he could be someone else, and how damaging that ability ultimately was for him.
Don seeks women who reflect how he wants to be perceived, what he wishes he were: beautiful and perfect-seeming? Betty. Interesting and modern? Midge. Grounded, sophisticated? Rachel, the Jewish department store scion. (And later on: thoughtful and sage? Dr. Faye. Carefree and loving? Megan.) Bobbie, the wife of comic Jimmy Barrett, for all her smarts and her cynicism, also represented a kind of blistering self-awareness, a level of honesty with oneself that Don found both tantalizing and terrifying. “Does it make you feel better to think I’m like you?” Don said to her, and he meant it as an insult. But part of him is like her, and it’s not a very healthy or appealing part.
“You don’t want to run away with me, you just want to run away.” Yeowch. Opposites attract, or so we’re told, but Don and Rachel were a little too perfectly opposite: He lives a lie about who he is, she runs the family department store business; he’s in a permanent state of exile, she’s one of God’s chosen people. Don tells her about the “two sorry people” who raised him, but he could be talking about the two of them.
Pete’s had a host of misery-related sexual encounters — and let’s not forget that he once raped his neighbor’s au pair — but nothing quite so sad as the flash of despair and anguish that lit up behind his eyes as he downed his drink, gazing at his pathetic reflection, while a prostitute called him a “king.”
The boss and the secretary, but so much more, too. It’s hard to picture Joan and Roger together together, openly and happily. Roger didn’t leave his wife for Joan, he left her for Jane, becaues his and Joan’s fatal flaw is that they could only ever really be an affair.