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The Worst Thing Don Draper Ever Did Was Hiding in Plain Sight (& Mad Men Fans Completely Overlooked It)

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At first glance, Don Draper appears to be an ideal individual, boasting physical prowess, good looks, intelligence, esteem, and wealth he earned himself. Yet, as viewers delve deeper into the seven captivating seasons, they gradually understand that Don Draper can sink to shockingly low depths. Throughout the series, Don Draper has committed deplorable acts, such as inciting a family member’s suicide and assuming another man’s identity after inadvertently causing his death.

In addition to numerous instances of infidelity, there are many despicable things about Don that some fans might have become accustomed to, but they may not fully understand how reprehensible his behavior towards Sylvia Rosen really is. Despite being one of the least popular characters, people might not have examined why it’s so simple to dislike her. A significant reason lies in the fact that she embodies Don during a particularly unsavory period of his life.

A Shameful Relationship Between Neighbors

When Don encounters Sylvia, he’s already been involved with numerous mistresses. His romantic entanglements span from two of his secretaries, multiple business clients, and even his daughter’s elementary school teacher. The recklessness of Don’s behavior is hard to comprehend and seems rooted in a tangled web of psychological issues, which may be linked to instances of emotional and sexual abuse he endured during his formative years.

Sylvia Rosen, the woman who captivates Don, is herself an unfaithful partner. To outsiders, she seems like a thriving physician, but her husband Arnold Allen devotes all his time to his work and often neglects her. Interestingly, Sylvia possesses a peculiar duality – she indulges in scandalous activities with Don, perhaps as a means of compensating for the absence of her busy husband, yet she is deeply religious and a dedicated Catholic. She frequently wears her cross and discusses her faith, but continues her secret affair with Don. Her hypocrisy has made her an unpopular character among fans of Mad Men>.

In summary, the missing piece in this puzzle is Sally Draper, the adolescent daughter who finds herself entangled between Don and Sylvia. As time goes by, Sally has grown up enough to realize that her father isn’t faithful in marriage. Adding to this, the typical disillusionment teenagers often feel towards their parents, Sally has all but lost any remaining respect for her father. Upon discovering his relationship with Sylvia, whatever admiration she once had for him is completely gone.

Why This Relationship Hurts the Most

If Don has been intimate with numerous individuals during the course of the series, what makes his relationship with Sylvia appear particularly distasteful? One explanation is that they are next-door neighbors. In the 1960s, a neighbor was frequently seen as more than just an acquaintance; it was a bond that could be considered close or even sacred. This was a time when people would often knock on each other’s doors to borrow sugar for a recipe, demonstrating a level of trust and familiarity.

Sylvia and Don don’t live in separate houses with white picket fences; instead, they reside in the same apartment building, often encountering each other in the elevator. These elevator encounters, notably, serve as striking reminders of their complex relationship. Frequently, Megan, Don’s wife, and Arnold, Sylvia’s husband, find themselves riding the elevator unaware that they are third wheels to this clandestine connection. The deception runs deeper than mere physical proximity; Draper and Sylvia also share a close bond in social circles.

As a film enthusiast, I find myself immersed within a unique social circle comprising Don, Megan, Arnold, and Sylvia. We often engage in double dates, finding joy not only in shared activities but also in each other’s company. It seems that, amidst our bustling professional lives, we have discovered a rare camaraderie.

In this series, I, Don, seldom nurture relationships beyond my work or indulge in extramarital affairs. Arnold, however, is one of the few individuals I genuinely appreciate. Our conversations and moments together are precious, as they offer a refreshing escape from our demanding professional lives.

Arnold put a lot of faith in Don, but unbeknownst to him, Don might have been engaging in an improper relationship with his wife. While Arnold wasn’t simple-minded about such matters—most reasonable individuals wouldn’t cheat with someone so close at hand—it still comes as a surprise that one would seek a mistress without leaving their own apartment building.

Don Still Treated Sylvia Terribly

One particularly challenging episode was “Man With a Plan” from season 6, where Don lived out a power fantasy over his mistress Sylvia. Instead of going on their planned date, Don shifts their plans to spending the night in a hotel room together. He instructs Sylvia to wait there while he goes to work, portraying it as an erotic game. However, Sylvia appears uneasy about being confined in the hotel room without a clear return time for Don. Despite her discomfort, she follows through with his plan. Yet, Don persists in repeating this scenario.

This episode portrayed Don as insensitive to social cues. He left a woman stranded in a hotel room with no entertainment, thinking she would find this amusing. It appeared that Don was living out a fantasy where women exist solely for his pleasure. To him, this is the role of women, and he tried to make Sylvia embody that ideal.

The Damage Don Did to Sally was Likely Irreversible

In a stealthy move, Sally sneaked into the Rosen residence to retrieve a heartfelt letter meant for Mitchell Rosen, their teenage son, whom Sylvia raised. Assuming the house was empty, she found herself unexpectedly witnessing her father engaged intimately with Sylvia instead. This scene might have caused more secondhand awkwardness for Mad Men viewers than any other, leaving Sally momentarily stunned and causing her to inadvertently drop a glass that caught the attention of the secretive duo.

Sylvia’s feelings of humiliation, distress, and anger were overwhelming, leading her to vent frustration by punching the bed and weeping. Meanwhile, Don pursued Sally while hastily adjusting his pants. His disregard for family values was evident as he hurried to appease Sally after she witnessed him. Rather than acknowledging his wrongdoings or treating Sally with dignity, Don tried to manipulate her perception by denying what she saw and asserted that he was aiding Mrs. Rosen instead. In essence, he attempted to deceive Sally.

In this situation, it’s not just making things worse, but it’s adding extra hurt to an already painful predicament. At her age, Sally is treated like a child, which is quite disheartening. Interestingly, Sally didn’t tell her mother, brother, Megan, or Arnold Rosen about the time she held her father with Sylvia. Instead, she carried the heavy burden of that traumatic event for years on her own. Throughout most of season 7, Sally had limited meaningful interactions with Don until quite late in the season.

As a devoted fan, I’d rephrase it like this: Sally isn’t just cutting ties with her father; she departs from home too. Upon learning about Sylvia and Don’s bond, Sally chooses to attend a boarding school as an escape from the tumultuous environment at home. Yet, it becomes evident that her father’s actions have had an immediate psychological impact on her, as she starts exhibiting troublesome behavior at this new institution.

In their interactions, Sally appears to be significantly distant from her father Don, a distance that feels more profound than typical teenage aloofness. Throughout much of their dialogue in the series finale, Sally expresses contempt towards him. While Don was once revered by Sally as almost divine, he now seems like an insignificant figure in her eyes. Sally had been aware of her father’s relationships with multiple women prior to the show, but witnessing it firsthand and then watching him try to hide it from her has significantly changed their relationship, a change that may be permanent for the rest of her life.

Gaslighting His Daughter is the Worst Thing Don Ever did

Among the numerous indiscretions Don has made to tarnish his image before fans, his affair with Sylvia and the subsequent drama involving his daughter caused significant harm to his standing within the ‘Mad Men’ community, arguably more than any other action. What makes this transgression particularly damning is that it appears as a descent from grace. Don had worked diligently to improve his reputation, or at least give the impression of a man who was above infidelity towards his wife.

Don managed to free himself from addiction (as far as he was concerned) and shared this news with [the person mentioned]. His children seemed to take a liking to Megan and the fashionable Manhattan apartment. However, Don’s self-destructive tendencies eventually pulled him back towards his old habits, causing him to squander everything. Following his relationship with Sylvia, it seemed as though Don was unable to undergo genuine transformation.

Despite Sally eventually becoming more lenient towards Don, it’s apparent that she recognizes, at her core, the profound flaws in her father. As she matures into adulthood, she might learn to tolerate these flaws, but the psychological scars are probably long-lasting. Don inflicted irreversible damage on his daughter, disregarding his wife and close friend in the process—all for a relationship that reduced his neighbor to little more than an object for his desires, rather than treating her as a genuine person.

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2025-07-06 01:51

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