AMC's Mad Men takes us back to the 1960s New York, a time in which relationships were based on different standards than they are today. Back then, women were expected to be stay-at-home moms, so it was important they marry well. Men, on the other hand, were the sole providers of their families, so they often crumbled under societal expectations. They enjoyed far more freedom than the underappreciated women did, though.
The inequality and rigid gender roles typically didn't lead to healthy marriages. Most of Mad Men's relationships are dysfunctional and based on lies. There are still several relationships that were overall successful. Some individuals were lucky from the start, while others had to work really hard on themselves before they were capable of committing to a genuinely loving relationship.
Most Successful: Ken & Cynthia
Ken is definitely among the most likable characters on the show because he didn't over-identify with his office job. He was one of the few characters that actually adored his wife and managed to be consistently dependable and emotionally available.
Cynthia and Ken didn't get a lot of screen time. From what we had seen, it's safe to say that they have a stable, loving, and exciting marriage.
Trudy & Pete
Trudy certainly deserved better than shameless Pete Campbell for a husband. She was nice, polite, and reliable, while Pete was going through one personal crisis after another. If she weren't such a powerhouse, their marriage wouldn't have survived all the ups and downs. Pete was a deeply insecure character, which to led him cheating on Trudy and fighting for approval at the office.
In the end, Trudy and Pete found their way back into each other's lives, which makes their relationship pretty successful in the grand scheme of things. For them, the problem was never a lack of love or horrible communication. Pete needed to do some growing up and Trudy waited patiently for him to come around.
Henry & Betty
In the rich and successful Henry Francis, Betty saw another chance at happiness and an escape from Don. She met him while she was pregnant with Don's child, but she knew that her marriage was in shambles anyway. Fans often do Betty a disservice at interpreting her as much worse than she actually is, but Henry didn't. He genuinely loved Betty, despite all of her emotional instability and moodiness.
Henry took Betty much more seriously than Don and he was utterly devastated after he lost her to cancer.
Roger & Marie
Third time's a charm: Roger is a light-hearted man and he finally found a perfect companion in Megan's mother Marie. They play-fight, they tease each other, and most importantly, they don't take themselves too seriously anymore. Roger is famous for his one-liners and Marie was the kind of a woman who knew how to appreciate them.
The last time we saw them was in a Parisian cafe, drinking pastis and smoking cigarettes. Even though there is no way of knowing for sure, it seems like this marriage is going to last and make both very happy.
Don & Megan
Don was never truly invested in Megan. He naturally spent a considerable amount of time with her because she was his secretary. At that point in his life, Don wanted to get his life in order. An opportunity arose in a form of Megan: a young, smart woman who was great with his children. For as long as Megan did what Don wanted her to do, they seemed happy enough.
In reality, Megan had very little room to express who she really was. Don hated the "Zou Bisou Bisou" performance and didn't like it one bit when Megan decided she wanted to become an actor. Megan should have been with someone who would appreciate her individuality.
Peggy & Stan
Besides Don Draper, Peggy was the most outstanding protagonist on Mad Men. She didn't have as much luck in love as her mentor, falling for authority figures, such as Duck or Ted. In the end, she found love in the arms of her liberal work colleague Stan Rizzo, which was a pleasant surprise.
In many aspects, they are the polar opposites of each other. Peggy is a fervent feminist, while Stan is a pot-smoking chauvinist. Their differences ignited the ion and chemistry between them. We have a good feeling that their relationship is going to last, but it will be strewn with conflicts.
Don & Betty
It's hard to say whether Don truly loved Betty or not. One thing is for sure, though: he saw the perfect trophy wife in the stunning and educated blonde. The two assumed the prescribed gender roles, which made Betty miserable. She hated being a stay-at-home mom. Other housewives bored her to death and she had no one to talk to.
Betty might have been a difficult woman, but Don only made the situation worse by being emotionally unavailable and secretive. Even though their marriage was highly dysfunctional, they did remain on good until Betty's untimely death.
Roger & Jane
From the moment Jane stepped into the office for the first time, it was clear that she was a social climber. She quickly went from being Don's secretary to Roger Sterling's wife. She was smart, curious, and insanely beautiful, so it's no wonder Roger considered her a catch. "Our souls are the same age," she told him once, and Roger quickly put a ring on it.
Their marriage wasn't as successful, though. After a profound LSD trip they shared together, they got a divorce. Jane gave Roger her best years, so she was clearly heartbroken about it.
Lane & Rebecca
Lane and Rebecca had clearly been married for years, but their marriage was highly abusive and depressing. Rebecca was a chronic complainer and Lane was a spineless enabler. She spent his hard-earned money without consulting him first, which led him to resort to embezzlement.
Rebecca didn't respect her husband at all, which is best reflected in her words to Don Draper after Lane's suicide: "You had no right to take a man like that and fill him with ambition." She didn't believe in him at all; no wonder he latched onto some random Playboy bunny to feel better about himself.
Least Successful: Joan & Greg
Joan is a majestic boss lady who could have had any man she wanted. Unfortunately, she rushed into a marriage with Greg who seemed like a great catch on paper: he was a young and ambitious doctor and Joan was ready to settle down.
Joan was an assertive and independent woman, which didn't sit well with Greg. He much preferred to spend time in the army, where he felt invaluable and respected. No wonder Joanie kept getting worse and worse: she always managed to pick the wrong men.