Mad Men: The Many Loves of Don Draper

Don Draper is the ultimate ladies’ man—but what’s his type? Who does he really love? And what do his many loves tell us about the man himself?


Mad Men: The Many Loves of Don Draper

Don Draper is the ultimate ladies’ man. But which lady does Don really love?

There are the mistresses who let him express a side of himself he usually keeps hidden, the wives who show us how he wants his life to appear, and the platonic loves who mean more to him than a lot of romances combined.

Beneath the superficial aspiration many viewers might feel watching Don’s love life—imagining what it’s like to have your pick of all these beautiful women—his romances serve an important story purpose. They reflect how we use our relationships to shape our ideas about who we are.

We can track the evolution of Don’s identity through the women who come and go in his life. So here’s our Take on how the many loves of Don Draper paint a portrait of the man himself.

Don’s Type

Don has a type. It can be hard to figure out what that type is, given the endless parade of all kinds of women passing through his life.

But on closer inspection, his kryptonite is a melancholy brunette, whether she’s deeply dissatisfied, grieving, or alienated. You might notice that this sounds a lot like a description of Don, so this tells us that through these trysts, Don is engaging with mirrors of himself. Their often secret or illicit nature reflects how Don’s true self is something he can’t bring out into the open.

The first is Rachel Menken, and you could say she’s the prototype when it comes to Don’s preference for sad brunettes. Even though the Don/Rachel romance is short-lived, it’s framed as one of the defining loves of his life. Show creator Matthew Weiner has gone as far as to say that Rachel is “the one.”

“What he really wants is he wants Rachel Menken, the one that got away, the life not lived.”—Matthew Weiner from an interview with the Television Academy Foundation

So why were these two so important to each other? Rachel is the first person to really see Don. When they meet in season one, both are “passing” by trying to disavow the parts of their identities that mark them as “other.”

Their shared feeling of alienation due to their backgrounds allows Don to confide in Rachel in a way we haven’t seen him do with anyone else. But even though Don takes a big step in starting to open up to Rachel, he’s not ready to do this fully. His secrecy and paranoia still win out.

The whole reason Don asks Rachel to run away with him is because Pete has just threatened to expose Don’s identity, so he’s acting out of fear rather than pure love.

Soon after their affair ends, Rachel gets married, and ultimately she dies young from cancer, which is an interesting similarity to two other key women in Don’s life—Anna Draper and Betty Draper. At its core, Don and Rachel’s relationship is a classic case of what might have been. It’s a great love that’s doomed by circumstance, timing, and fear of what society will think.

The tragic potential of this love is captured in Rachel’s discussion of the word “utopia.”

“The Greeks had two meanings for it: ‘eu-topos,’ meaning ‘the good place,’ and ‘ou-topos,’ meaning ‘the place that cannot be.’”—Rachel from Season 1, Episode 6 “Babylon”

With this line, the show raises an agonizing idea: what if the person you love but can’t be with—the one who got away—is the great romance of many people’s lives?

In season seven, years after their affair has ended, it’s implied that Don has been dreaming about her for most of the series. When Don goes to Rachel’s Shiva, her sister says: “I know who you are, “suggesting that he loomed large in Rachel’s mind, too.

So through this relationship, the show points out that the person you connect with most in an authentic way—or the one who moves your heart most deeply—sadly may not feature for much screen-time in your life.

“This is it. This is all there is. Feelings slipping through my fingers like a handful of sand.”—Don from Season 1, Episode 10 “Long Weekend”

Many of us, like Don, don’t follow our hearts in that brief moment when we have the chance, and then spend the rest of our lives wondering, or trying to recreate the lost opportunity with new people who remind us of that one-who-could-have-been.

While Rachel speaks to the disconnected outsider in Don, his neighbor Sylvia Rosen gives expression to another part of his identity: his past.

The show links Sylvia to Aimee, a prostitute who worked at the brothel where Don grew up. In flashbacks we see how Aimee mothers young Don when he’s sick, but also takes his virginity. And the complex dynamic he had with Aimee comes through in the oatmeal ad Don creates, where the woman inspired by Aimee appears to be the young boy’s mother.

Like Aimee, Sylvia is a madonna/whore figure. She’s a Catholic woman who comforts and cares for Don, but they also have a very carnal connection.

So this affair is Don’s way of trying to rewrite the past, of taking charge in this relationship with a woman who reminds him of Aimee, because he wasn’t in control with the real Aimee.

It’s no coincidence that Don asserts this power with Sylvia while he’s feeling impotent in his marriage to Megan.

Sylvia makes him feel needed again. He sees her arguing with her husband about money and later gives her cash. He calls in a favor to stop her son from being drafted, enjoying being the big hero who saves the day.

But the most revealing episode in Don and Sylvia’s relationship is when she tells him: “I need you, and nothing else will do.” These words drive Don wild. He even makes Sylvia repeat them when they meet at a hotel to have sex. And they seem to trigger an even greater need for control deep inside him. From here on out almost everything he says to Sylvia takes the form of a command.

“I want you to crawl on your hands and knees until you find them.”—Don in Season 6, Episode 7 “Man With A Plan”

This is about him making Sylvia into someone who can’t desert him, reminding us again of how his childhood trauma and fear of abandonment inform this and all of Don’s relationships.

When Sylvia ends their affair, Don gets desperate. He comes as close as Don Draper can come to begging, lurks outside her back door, and keeps trying to restart their relationship. As Weiner said, “He could take or leave Sylvia until she rejected him.” Sylvia was supposed to be someone he had total control over, but even in this rewriting of history he couldn’t possess her enough to cure his feelings of powerlessness and self-hatred. While we could buy into the romance of Don’s relationship with Rachel, his affair with Sylvia is one of the lowest things he does. He’s sleeping with his friend’s wife right under the man’s nose, and brazenly lying to his own wife.

So it’s fitting that the Don/Sylvia relationship ends in the most humiliating way possible. This creates another parallel to his encounter with Aimee, because that relationship also ended in shame. But it’s significant that just two episodes later, we see Don come clean about his identity at work, and start opening up to his kids. He had to face the past, and even relive parts of it, in order to really commit to changing. It takes another woman to reveal exactly how Don’s affair with Sylvia has changed him.

His relationship with Neve Campbell’s character, who is unnamed on the show but credited as “Lee Cabot,” is one of the show’s briefest. Their story lasts the length of a plane ride, but over these hours they develop a deep emotional intimacy as this woman reveals that she is grieving her dead husband.

“I mean we literally said, ‘Let’s build Don Draper’s ideal woman.’ Right down to the fact that she’s sad. There’s a depth to that, to the grieving, that Don’s attracted to.”—Matthew Weiner from an interview with the Television Academy Foundation

So it’s a surprise when at the end of the plane ride, Don decides not to take this fledgling romance any further.

Weiner has said, quote, “that woman has everything that Don Draper loves, and his resistance of her shows his attempt to recommit to his marriage, and his attempt to become a better person in some way.”

The mysterious waitress Diana is the final woman of Don’s type with whom he has a significant relationship. Diana represents mourning what’s lost.

From their very first meeting, Don feels like he knows her. He meets Diana soon before learning that Rachel died, so it’s almost like she’s the ghost of Rachel. Diana really is the make-up or do-over Rachel, in that Don could realistically have a relationship with her. By now he’s separated from Megan, and the timing is right. He and Diana forge a powerful connection over their shared experiences of loss.

But what stops this relationship from becoming more is that Diana is too damaged. The tragedy in her past has made her determined to cut all positive feeling out of her life. So this woman is really a cautionary tale for him. Her story reminds him that he needs to push through the pain to become a better, happier version of himself.

If we look at the similarities between Rachel, Sylvia, Diana, and Lee, we see that there is a spirit of a woman Don loves that manifests in each of them. This sad woman embodies the tragedy of his life, that he can’t fully realize or connect to the person he is in a positive way.

The Wives

If the women who fall under the umbrella of “Don’s type” reflect who he really is, Don’s two wives show us who he wants to be. Betty and Megan remind us that this is a key part of marriage, cultivating and presenting a certain joint image to the world.

As Don’s first wife, Betty embodies the WASP elite that he aspires to be a part of. The couple does achieve the suburban, white picket fence ideal, but this beautiful image masks a deep dissatisfaction and emptiness they both feel. Don spends a lot of their marriage cheating on Betty and keeping secrets from her. He doesn’t believe he’s worthy of this woman’s love. He fears—correctly—that she would never be able to accept him as Dick Whitman. And yet on some level he wanted her to discover the truth, because he couldn’t have a complete experience of love from a wife who doesn’t even know who he is.

After Don and Betty’s divorce, Don briefly tries to replicate Betty’s polished, upper-class pedigree with Bethany Van Nuys, who is essentially a young Betty Draper wannabe. But Don is bored by Bethany, showing that he’s outgrown his interest in achieving that conventional ideal. Instead he goes in a totally different direction by marrying his secretary Megan Calvet, who represents a fresh start.

The biggest reason Don falls for Megan is her idealized view of him. She helps him believe he’s a good person as he emerges from the wreckage of his divorce.

On the surface, vivacious Megan is a stark departure from Betty. Yet this marriage is again Don’s way of proving something about himself. Aligning himself with this young, modern woman shows he wants to present as cool and “with it” as he enters middle age. Sexy, liberated Megan is the envy of his settled friends, and her talent for advertising suggests that, as a working woman, she’ll be Don’s intellectual equal. Yet even though he enjoys the idea of Megan’s free, hip lifestyle, he doesn’t really like this openness in practice, as we see when he hates the surprise party Megan throws for him. So as much as he initially likes the image that his second wife helps him present, over time their private incompatibility becomes harder and harder to overcome.

Don’s marriages make it clear that our choice of spouse is often based on two things: the face we want to present to the world, and the way we want to think of ourselves. Don sabotages both his marriages, so this reveals that, even if he succeeds at creating that perfect image of himself for a while, over time he himself can’t buy into the lie, and that’s why he can’t accept his wives’ love.

The Lesser Loves

The other women who show up in-between these significant romances also reveal what’s going on within Don at any given moment. He’s with many, many other women over the course of the show, some just for one night, but we’re going to talk about the ones who do stick around a little longer and have an impact on his life. The most common thing Don seeks in his mistresses is an escape.

Midge, the first mistress we meet in season one, lives the antithesis of Don’s and Betty’s married life. She is an independent artist who isn’t interested in a traditional cookie-cutter life. This is the appeal she holds for Don. She’s like a reprieve from his day to day existence.

In season three, Sally’s teacher Suzanne Farrell intrigues Don with her free-spirited nature, and becomes another vacation for him. This woman is a breath of fresh air in his stifling suburban family life.

In season two, Don’s affair with his client’s wife Bobbie Barrett reveals that for him, sex is very much about power. This tryst is an escape of a different kind. It’s all about releasing the darker impulses they can’t act on in their normal lives.

Season four’s Dr. Faye represents the potential for Don to have a healthy, mature relationship. They meet when he’s a single man and she is his equal, an accomplished and intelligent professional woman who sees him clearly. When they do start dating, they do it with their eyes open and their relationship has an emotional honesty that’s been missing in a lot of Don’s past love affairs. But season four Don isn’t ready to deal with his problems in a realistic way, which is why he chooses to dive headfirst into yet another escapist relationship rather than continue things with this more appropriate partner.

The True Loves

Two of the most profound relationships Don has on the show are with women he’s not romantic with at all.

Anna Draper represents the power of unconditional love. She’s different from all the other people in Don’s life in a very significant way: from the first moment she meets him, she knows his secret. Don spends so much of the series going to great lengths to hide who he really is, out of fear that people would reject him if they knew the truth. But loving, open-hearted Anna disproves that notion.

“I know everything about you, and I still love you.”—Anna from Season 4, Episode 3 “The Good News”

So his bond with Anna makes us realize that he’s cheating himself out of a lot of love he potentially could experience by not being upfront with others.

Finally, Don sees his protege Peggy as a part of him, seemingly even more than he does his actual children. Like him, she enters the advertising world as an outsider and experiences a life-changing trauma, and she shares his exceptional talent and work ethic. When Don champions Peggy’s career and passes on his survivalist philosophy to her these are gestures of love that he wishes someone had shown him.

When Anna dies, Don sees a vision of her ghost, and as she looks down on Don and Peggy it’s like she’s satisfied that Peggy is taking her place as the most important woman in his life, who also knows him completely, though in a different way.

When Mad Men ends Don is a single man, probably not for long, if his romantic history tells us anything, but his relationship status is a reminder that this story has always been about this ladies’ man’s journey with himself. Weiner has said that Don hugging Leonard in the finale represents “love for yourself.” By showing compassion to this stranger, Don is really extending a hand to his inner Dick Whitman. So while Don Draper spends so much of the series searching for emotional fulfillment in other people, in the end, the love he needed most of all was his own.