The characters of Mad Men are hardly known for their functional relationships. Between the frenemies, marriage betrayals, and office backstabbings, it's a wonder the series didn't end in some sort of tragic Shakespearean bloodbath.
In the world of 1960s Madison Avenue advertising, image is everything. So even if Don, Peggy, or any employee at Sterling Cooper, would cheerfully throttle their boss or spouse, they grin in bear it all in the name of keeping up appearances. No wonder everybody drinks so much. Still, throughout all the booze-soaked misery, there are a few souls who find flickering moments of love and respect for each other. Here are the five best and five worst relationships on Mad Men.
10 Worst - Don & Megan
Never marry someone in the hope that they will make you a better person. Don falls for Megan after suffering a bout of perpetual loneliness. With her warmth and crackling personality, she's like a roaring fire after a long day out in a snowstorm. From Megan's perspective, Don's the total package: handsome, charming, and successful.
They seem like a white-hot match made in heaven. Don is even faithful for a handful of episodes. But Don and Megan make the classic mistake of getting hitched while they're still in the honeymoon phase. Once it's over, Don goes back to his philandering ways. He becomes resentful of Megan's insecurities, while simultaneously holding her back from her acting career. Next time Megan will know—if he's already broke, don't think you can fix him.
9 Best - Peggy & Pete
Every relationship can get a little rocky, but Peggy and Pete's is a treacherous cliff. How do they not fall over the edge? They stop sleeping together. Sex, for all its thrills, complicates things. When some after-hours hanky-panky results in Peggy giving birth to Pete's child, she keeps mum about it and gives the child up for adoption. She may have feelings for the married Pete, but she certainly doesn't want to be tied to him forever.
Peggy ends up telling Pete much later, after he professes his love for her. For all his privilege, Pete resents the confines of his blue-blooded life and is drawn to Peggy's freedom and rapidly growing independence. Both characters mature over the years, as does their relationship. It becomes one of cultivated platonic respect.
8 Worst - Don & Betty
When we first meet the Drapers, Don is already stepping out on Betty, bedding every brunette with a slim waist and a sad story. But when he mixes things up by picking another blonde as his mistress, Earth is thrown off its axis. Despite Don getting away with his affairs of the past, Betty is tipped off about this one. Don doesn't even give her the courtesy of 'fessing up, forcing Betty to spin her wheels and tear her hair out. Hey, Don will tell you that trust is just an ad campaign invented to sell insurance.
Then there's Betty. When she's not cold and distant, she's prone to throwing childlike temper tantrums. Don's only too happy to point out her immaturity but, just like with Megan, bristles against Betty showing any real independence. These two really bring out the worst in each other. Eventually, Betty finds a man who truly loves her, leaving her dumpster fire of a marriage.
7 Best - Betty & Henry
Meet Henry Francis, the man who saved Betty from the bowels of marital hell. Are Betty and Henry the most sizzling couple of the series? Not by a long shot. But they're sweet together. When they first meet, there's an attraction that's deeper than the physical.
This is the second marriage for both of them and neither are under any fairy tale delusions. They function well together, showing patience and understanding for the other's faults. After Betty makes a scene by slapping Sally, Harry could have raked Betty over the coals. Maybe he should have, but what would that accomplish? By him staying calm, Betty is able to cool her jets. Henry and Betty provide the closest thing to a harmonious home that the Draper kids will ever get.
6 Worst - Don & Sally
There's no doubt that Don loves his daughter, but his fathering skills are about on par with a teenager being forced to care for an egg in home ec class. It's a good thing Sally isn't actually an egg, or she would have broken long ago. When Don's not ditching Sally's birthday party, he's traumatizing her with his recklessness. Walking in on Daddy in the throes of passion with his married neighbor has to leave some emotional scarring.
Unlike Betty, Don never raises a hand to Sally. But it hardly bodes well if the best thing we can say about Don's parenting skills is that he doesn't beat his children.
5 Worst - Joan & Peggy
Joan is a bully to Peggy right from her first day. When she's not disparaging Peggy's appearance, Joan is undermining her accomplishments. Though she'd die before admitting it, Joan resents Peggy for forging a path to success that's not paved with beauty and flirtation.
For her part, Peggy tries ever so hard to get into Joan's good graces. Maybe Peggy's fed up with trying, or maybe she's jealous of Joan's allure, but when a bunch of male execs humiliate Joan in a meeting, Peggy is the opposite of supportive. She blames Joan for bringing the negative attention on herself. Forget any of the show's romances; this relationship is the real heart breaker. How awesome would it have been if they teamed up instead of cut each other down? They come close at the end of the series but alas, it was never in the cards.
4 Best - Peggy & Stan
Some relationships are built on love at first sight while others are a slow burn. Peggy and Stan can't stand each other at first. She thinks he's a pompous pseudo-bohemian and he thinks she's a corporate Pollyanna. But as they work together, Peggy and Stan discover that the other is truly excellent at their job, and they make a dynamic creative team.
Even after Peggy leaves the agency, she still maintains a friendship with Stan. The series finale finds him unexpectedly confessing his love to Peggy which she reciprocates, surprising not just the viewer, but herself. Their final appearance is of Stan massaging Peggy while she works, making it clear that she can have both a man and a burgeoning career.
3 Best - Joan & Roger
Roger incinerates every relationship he's a part of. So how do these two crazy kids keep their love alive for over a decade? They never make it official. Joan and Roger work together because Joan makes it clear she doesn't need him. When a romance comes out of want as opposed to need, there's a lot less emotional skin in the game. Joan and Roger are free to let the good times roll.
But that doesn't mean their decade-plus affair is just about sex; there's real love between them. Roger shows Joan a respectful admiration that he certainly doesn't give to any of his spouses. Joan ends up getting pregnant with Roger's child and though she passes it off as Greg's, Joan wants Roger in baby Kevin's life. To be clear, this is for Kevin's sake, not Joan's. Her epic ending shows that Joan doesn't rely on anyone but herself.
2 Worst - Joan & Greg
There are no words to describe the bottom-feeding evil that is Greg Harris. Him raping Joan in Don's office is one of the most disturbing, stomach-churning moments television has ever seen. Viewers are crushed for Joan, who follows through with marrying this monster. From her perspective, she would never be believed if she spoke out. There's every possibility that people would perceive Greg as an upstanding man of medicine and Joan as an aging woman desperate for attention. In the short-term, Joan sweeping her assault under the rug is her way of coping.
Throughout their marriage, Greg continues to be a selfish jerk. Unhappy with the trajectory of his medicine career, Greg becomes a doctor in the army. Of course he doesn't bother consulting Joan. For years, she keeps her feelings held in—save for that glorious moment when she smashed a vase over Greg's head—but Joan is done being deferential. Ever the class act, she delivers these two oh-so satisfying words to Greg: "That's it."
1 Best - Don & Peggy
To say their relationship is tumultuous is like calling Vesuvius a little eruption. When things are copacetic, Don and Peggy have the kind of exquisite work chemistry that makes us think they could take over the world. But when they're at each other's throats...run for your lives, lest you get burned by egotistical lava.
Don clearly sees Peggy's visionary talents but withholds praise. The result is that Peggy feels the need to jump through hoops to please Don and eventually gets fed up, leaving the agency because of him. But great partners always find a way back to each other. Don't get us wrong, Don's a total jerk to Peggy. He doesn't deserve her friendship or her love. But remember, this is a workplace show. Peggy is able to follow Don's devil-may-care example and she's able to find the confidence that Don has in her all along. And Don, throughout all his relationships, feels the deepest connection to Peggy, whom he calls in his series finale moment of crisis. Don and Peggy's relationship is complex and dark and problematic. It's the perfect embodiment of the show itself.