Ranked: Don Draper’s Relationships On Mad Men, From Most To Least Dysfunctional

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Bear in mind, with this guy, it's all relative.

As a woman who loves Mad Men, which returns to AMC this Sunday, I'm both besotted with and disgusted by Don Draper, who somehow manages to be both tenderly flawed and nakedly brutal at the same time. Don burns through women faster than some people change socks. Some of those women try to change him (and fail). Some try to redeem him (and fail). Some try to find some spark of humanity in him to connect with (and fail disastrously). Many have amazing sex with him, but so far, none have saved him. Don and his women are often so damaged by their encounters that we thought it would be interesting to rank these relationships by how healthy they are for both players. Below, Don Draper's sexual relationships, ranked from most to least dysfunctional. 

9. Allison

This relationship was a trainwreck we saw coming from a mile away: the shy, devastatingly innocent secretary overwhelmed by Don's lust and good looks. True, Don is single (and drunk) when he casually wrecks her illusions about men, the safety of her workplace, and her self-worth, all in one fell swoop. But his almost perfunctory advance on her, seemingly from a need to feel power over something female in the fallout of his divorce, represents the worst kind of rebound sex. It's all about him; she just happens to be there. And she lets him do it out of a misguided sense of affection that he'll never pay back — or even really understand. 

8. Bobbie Barrett

Don's sexual violation of Bobbie while at dinner with his wife might be the most reprehensible thing he's done in four seasons of reprehensible things. It's not consensual or sexy, and the most dysfunctional thing about it is that Bobbie is strangely enthralled by his hate-sex, revealing an intensely jaded woman so used to dealing with powerful men that she embraces their misbehavior and even revels in it. Both of them are fucked up, but they seem almost mutually fucked up, and unlike Allison, Bobbie seems to go into her fling with Don with eyes wide open. She knows exactly how terrible he is, and disturbingly, that appeals to her.

7. Betty Draper/Francis

In some sense, the entirety of Mad Men is about unpacking Don and Betty's relationship — the perfect 1950s relationship that looks immaculate from far away but reveals its fissures as you zoom in. Betty buys into the illusion Don Draper tries to live, but as she slowly realizes that the man who reinforces her self-image is a sham, she herself begins to implode. She and Don eventually force each other to confront the other's illusions, and destroy their life together. The whole thing rates pretty high in terms of dysfunction.

6. Suzanne Farrell

Don has a strange relationship with beatniks, hippies, and other free spirits: he's drawn to them, but he also holds himself above them as a realist. It's just bad news to get involved with your kid's teacher, but Suzanne seems to embrace Don as readily as the complications of her own life. Don even seems willing to take his affair with her further, but the plot cuts it off. Not super emotionally healthy — I mean, cheating on your wife with your daughter's third-grade teacher, right? — but on the Draper scale, that's not even that bad. (It's also, like much of the third season, not that interesting.)

5. Joy

Those California girls, they're undeniable (I'm told). As her name suggests, Joy is less a full-fledged character than an escape for Don, who uses her to disappear from his life for a few weeks in California. There's not much else to say about this seemingly carefree young woman. Both she and Don seem to know what they want from each other from the get-go, and manage to have a fun, no-strings-attached vacation together. No harm, no foul — except to Betty, who remarks pointedly, "It must be nice, needing time and just taking it," when Don returns from his vision quest.

4. Megan Calvet

Hard to say at this point, but Megan may be the rare Draper paramour who's tougher than she looks. In striking contrast to poor Allison, Megan is steely and seemingly unruffled by the emotional maelstrom that is Don Draper's inner life. Granted, a sudden engagement to someone you barely know is not a good sign, but Megan doesn't seem to harbor any romantic fantasies about perfection, which are part of what brought Don and Betty down so hard. Nothing illustrates her pragmatism better than the spilled milkshake in the Season 4 finale: Don and the kids tense up as if still expecting an explosion, but Megan takes it in stride.

3. Midge Daniels

In Mad Men's beautifully written pilot, Don wakes up with Midge, his cool, modern Village mistress. It's unclear how long they've been involved, but they move around each other as if they're very well-acquainted. Even though Midge ends up as a heroin addict, I rank this one relatively high in emotional healthiness because Midge seems like she can take care of her self. She expects very little from Don: she knows he's married, she knows he sleeps with other women besides her, and she doesn't really care. She has her own life and career, and doesn't need Don for fulfillment. She's very much in the moment with Don, and Don, in turn, seems to be himself with Midge in a way that he is not able to with others. 

2. Rachel Menken

Rachel and Don have screen-torching chemistry from their first meeting, and their relationship is a tricky negotiation of power, identity and passion. If Don feels he can be himself with Midge, with Rachel he realizes who he could become — or, to be exact, who he could have become, if he weren't a complete sham. She's too smart and too grounded to buy into his fantasies (in retrospect, you can see the end of their relationship beautifully foreshadowed by the conversation they have over drinks in the first episode); she closes the door on their relationship with grace and dignity, and finds someone who deserves her within a year. It's a tragedy that Don can't make this work, but that tragedy is the continuing tragedy of Don Draper, scam artist.

1. Faye Miller

Until he blows it, Faye and Don have the most normal and stable relationship of Don's life. They're both powerful and intelligent, and meet each other as professional equals, but she makes the mistake of trusting him to be more of an adult than he actually is — though for a minute, it looks like he's actually going to get there. He manages to confess to her about his past, and he opens up about his ex-wife, his children, and his work. And then he runs from it, into the arms of a woman whose adoration is less challenging. Will we ever be able to forgive him? We may find out in Season 5.

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