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On the surface, Don Draper seems like the perfect human being. He’s well-built, handsome, intelligent, respected, and filthy rich because of being self-made. However, as fans of Mad Men continued watching through the seven fantastic seasons, they came to realize just how low of a person Don Draper can be. Don Draper has done astonishingly awful things throughout the series, ranging from causing a family member to commit suicide to stealing a man’s identity after accidentally killing him.
Among the awful things Don has done are countless acts of infidelity, which may have numbed some fans to how dreadful his relationship with Sylvia Rosen truly is. Sylvia is one of the least liked characters, but many fans may not have looked deeply into why it’s so easy to hate her—and a lot of it has to do with the fact that she represents Don at his most disgusting era.
A Shameful Relationship Between Neighbors
By the time Don meets Sylvia, he has already gone through an army of mistresses. His relationships have ranged from his secretaries (two of them), to several of his clients, and even to his daughter’s elementary school teacher. The recklessness of Don’s actions is difficult to explain and is tied to a network of complex psychological problems he has developed, likely stemming from his experiences of emotional and sexual abuse in his youth.
Don’s mistress of interest, Sylvia Rosen, is also an adulterer. On the surface, she appears happily married to a successful physician. However, her husband, Arnold Allen, is entirely dedicated to his craft and often does not spend enough time with her. Sylvia has a strange duality—she readily engages in scandalous behavior with Don, likely to fill the void left by her absent husband, while also being a fiercely devout Catholic. Sylvia is often seen wearing her cross and speaking about her faith, yet she continues her deceptive relationship with Don. This hypocrisy has contributed to her lack of likability among Mad Men fans.
The final piece in this puzzle is Sally Draper, the innocent teenage daughter caught in the middle of Don and Sylvia. By this point, Sally has matured enough to already know that her father is not a loyal husband. Combined with the general lack of trust and empathy many teenagers feel towards their parents, Sally has nearly depleted whatever respect she once had for her father — and her discovery of his relationship with Sylvia brings it down to zero.
Why This Relationship Hurts the Most
If Don has slept with many people throughout the series, why does his relationship with Sylvia come off as especially distasteful? The primary reason is that they are neighbors. In today’s society, a neighbor is often just a stranger, but in the 1960s, a neighbor represented a close and even sacred relationship. This was an era when it wasn’t uncommon for neighbors to knock on each other’s doors to borrow sugar for a recipe.
Sylvia and Don aren’t even separated by a white picket fence—they live in the same apartment building and frequently see each other in the elevator. These elevator rides, in particular, are important visuals that emphasize just how twisted their relationship is. Megan, Don’s wife and Arnold, Sylvia’s husband, are often riding it unknowingly as a third wheel. The deception goes deeper than just physical proximity. Draper and Sylvia are also close in a social sense.
Don, Megan, Arnold, and Sylvia have formed a social circle. The two couples frequently go on double dates, and to make matters worse, they genuinely enjoy each other’s company. Throughout much of the series, Don has almost no relationships outside of work or adultery. Arnold was one of the few characters Don truly liked, and the two regularly talked and spent time together in an environment completely separate from their busy professional lives.
Arnold placed a great deal of trust in Don and was entirely unaware that he could be having an inappropriate relationship with his wife. Arnold wasn’t naive in his thinking—most rational people, even those who commit adultery, wouldn’t sleep with someone that «close to home». There’s a shocking level of audacity in not even going outside your own apartment building to find a mistress.
Don Still Treated Sylvia Terribly
One of the most difficult episodes to get through was season 6’s «Man With a Plan». Don was flexing his power and living out a fantasy of total control over his mistress. Don cancels his date with Sylvia and instead pivots to them staying inside a hotel room. He then tells her that she has to wait there while he goes to work. Don tries to spin it as a sexy game, but Sylvia is clearly not comfortable with the idea of being stuck in a hotel room without knowing when he will come back. She goes through with it, but Don continues to repeat this process.
This episode made Don seem socially tone-deaf. He had this woman stuck inside a hotel room with nothing to do, and in his mind, this was supposed to be enjoyable for her. Don was clearly acting out a fantasy of having a woman who exists solely to please him. In Don’s mind, that is what women are for, and he attempted to make Sylvia the true personification of that belief.
The Damage Don Did to Sally was Likely Irreversible
Sally had snuck into the Rosen household to retrieve a letter of affection she had left for Mitchell Rosen, the teenaged son of Sylvia. She presumed no one was home, but she quickly discovered her father making love to Sylvia. Her reaction likely generated more secondhand embarrassment for Mad Men fans than any other scene, and she was so shocked she dropped a glass, which quickly caught the attention of the cheating couple.
The shame, embarrassment, and anxiety were so intense that Sylvia is seen punching her bed in frustration while breaking into tears as Don runs after Sally while pulling up his pants. Don has so little respect and self-awareness regarding his family that he quickly tries to reconcile with Sally after she catches him. However, instead of treating Sally like a person and admitting that what he did was wrong—or even attempting to explain his actions—Don tries to gaslight her. He insists that she didn’t know what she saw and claims that he was “helping” Mrs. Rosen.
This adds significant insult to an already terrible situation, as Sally is a teenager at this point and is being talked down to as if she were still a child. Sally never revealed to her mother, brother, Megan, or Arnold Rosen that she had held her father with Sylvia. Instead, she internalized the traumatic experience for years. For most of season 7, until toward the end of the series, Sally has almost no meaningful contact with Don.
Not only does Sally distance herself from her father, but she also leaves her mother’s toxic environment. Discovering Sylvia and Don’s relationship leads Sally to decide to go away to boarding school—it’s the only way she can find any peace of mind from her turbulent homes. However, fans quickly see the immediate psychological damage her father caused, as she engages in delinquent behavior at school.
Teenagers often go through periods of coldness toward their parents, but Sally’s indifference during her interactions with Don feels much deeper. Until the end of the final season, she speaks to him with disgust. Don, who for most of the series was like a god to Sally, seems almost like a peon to her. Sally had known her father had relationships with many women before, but physically seeing it — and then watching him try to pretend it never happened — altered her relationship with him, likely for the rest of her life.
Gaslighting His Daughter is the Worst Thing Don Ever did
On the long list of misdeeds Don has committed to embarrass himself in front of fans, his relationship with Sylvia—and the fallout involving his daughter—did more to damage his reputation among the Mad Men community than almost any other action. Perhaps what makes it worse than many of his other acts is that it feels like a fall from grace. Don had built himself into a more respectable person, or at the very least someone who seemed to have no interest in cheating on his wife.
Don cleaned himself up from substance abuse (by his standards) and told Megan his true identity. His kids appeared to like Megan and the trendy Manhattan apartment. But Don’s destructive behavior led him to revert to his old ways, throwing it all away. After his relationship with Sylvia, it felt like Don could never truly change.
Although Sally eventually softened toward Don, it’s clear that, deep down, she understands just how deeply flawed her father is. She may come to accept it as she grows into adulthood, but the psychological damage is likely permanent. Don did irreversible harm to his daughter while also massively disrespecting his wife and close friend—all for a relationship with his neighbor, whom he treated more like a sex object than an actual person.
