Power Ranking The Many Relationships Of Don Draper Over The Years On ‘Mad Men’

Mad Men is about to come to an end, and so what better time to take a look back at the epic man-whoring of the one, the only, Don Draper? Of course, if we recounted all of Don’s ass-crushing exploits, we’d need to launch a new site just to handle all the bandwidth, so let’s just focus on his many, many relationships that extended beyond a drunken one-time bonercoaster ride in an airport hotel room.

Yes, these are the relationships that helped define Don for us over the years – for better or worse – and because we’re bros of science, let’s rank them all, right here and right now, from “What the hell was he thinking?” to “She’s the one, Don!” Of course, one or two might slip through the cracks here, but don’t blame me, blame Don’s voracious penis. And with that said, let’s begin.

12. Betty Draper

We’re starting off hot here. I know I’ll catch hell for this, but come on, Betty sucks. She’s awful. She’s a horrible mom, she’s mean to everyone and she’s the type of woman who will lead you down a rabbit hole of misery and insanity, chasing that sweet, sweet ass until you realize too late that it’s attached to a succubus who will steal your soul and all your joy. Maybe I’m getting a little carried away, but damn it, just take a moment and try to imagine being married to Betty Draper and spending your entire life enduring her sneers, her wheedling and the knowledge that you’re constantly on the verge of having to deal with an epic temper-tantrum. ‘Nam was less traumatizing than that.

11. Bethany Van Nuys

Bethany Van Nuys was beautiful. She was set up with Don by his bro, Roger Sterling, and Roger’s hot young wife, probably because Roger wanted an actual adult to hang out with when they were all out on the town, but the problem is that Bethany was boring as hell. How boring was she? Don dumped her even though she was willing to blow him in the back of a cab. She was so boring that Don’s boner even fell asleep, and that little dude (or big dude if you’ve seen those pictures of Jon Hamm’s ham trying to escape his pants) is always awake and ready to go.

10. Candace

The lovely Candace was a hooker that Don, uh, hooked up with for a while because, well, why not? Sure, that’s not exactly the basis of a quality relationship, but it is the basis for a stress-free carnival of sex and sometimes that’s all the heart desires. I read that in a Hallmark card once, I think. Still, it’s hard to say a relationship really has any future when one of the participants won’t even tell you her last name. Then again, maybe that’s the best relationship. Who’s to say?

9. Bobbie Barrett

Bobbie Barrett was the wife of one of Don’s pain-in-the-ass clients, so naturally, he boned her. That’s always a bad idea for reasons both business and personal, but what the hell, sometimes the boner wants what it wants. I suspect Don probably just got off on the revenge factor since her husband was a douchebag, but Bobbie did have a smoldering sort of sex appeal and she knew what she wanted, and hey, sometimes that’s all a dude wants. At least Don knew this one’s last name.

8. Midge Daniels

Don’s Village-dwelling artist sidepiece, Midge would rank higher – she’s sexy, she’s smart and Don actually seemed to like her for a change – but she loses points for basically being a proto-hipster who became a junkie and tried to hit Don up for drug money after they broke up. That’s, uh, that’s a pretty big drawback. Their relationship worked best when they could just hide out together in her loft, but shitty friends ruin everything, especially when they start lecturing you about being a suburban white dude. It was like hooking up with a Twitter activist, and nobody needs that.

7. Sylvia Rosen

The wife of Don’s doctor neighbor and friend, Sylvia was sexy and Don totally fell for her, but… well, read the first part of this sentence again. This was doomed to failure from the start, and on top of that, it made Don’s daughter realize he was a fucking degenerate after she walked in on them going at it. Still, Don got to bone Lindsay from Freaks & Geeks, and that’s got to be worth something.

6. Suzanne Farrell

Suzanne Farrell was his daughter’s teacher so of course Don ended up sexing her. And, of course, Don ended up destroying her because that’s just how Don rolls. It’s sad because she was pretty, smart and she and Don actually got along, which is always a welcome change of pace for our favorite ad-man/alcoholic/sex-addict/father-of-the-year. Still, there was just something missing here, that spark that a dude like Don really needs to kick things up a notch. Without it, you just end up waiting in the car while Don gets back together with his horrible wife. Poor Ms. Farrell.

5. Megan Calvet

Megan is the sort of woman who ends up killing a dude by giving him a heart attack in bed or while working himself like a dog just trying to make her happy. I mean, Jesus, there’s a reason why every dude in the room practically reacted like a goddamn cartoon character, eyes all bugging out, hearts thumping, when she sang that “Zou Bisou Bisou” song.

But here’s the thing about Megan: she and Don just aren’t right for each other. She wants more than he can give her, and he needs a partner who’s already secure, not someone who’s constantly looking to break away and become a star. They’re just at different places in their lives and that shit just doesn’t work. Plus, she looks disturbingly like a young Freddie Mercury. I’m so sorry, you’ll never not see that now that I’ve pointed it out.

4. Dr. Faye Miller

This is what I meant by Don needing to be with someone who’s already secure and cool with her place in his life. She was a doctor, she was hot, and she and Don could actually connect as adults. Of course, Don left her in the lurch by running off to marry his secretary, Megan. Don’s gonna Don, yo.

3. Rachel Menken

Don’s OG sidepiece – at least from our perspective, who knows how much ass he crushed prior to the events of the show – Rachel was smart, beautiful, an heiress, and she was pretty chill. In another universe, she and Don could have settled down and had a totally tranquil life together. Of course, in this universe, Don was already married and fucked everything up.

2. Anna Draper

Sure, they never actually hooked up, but Anna Draper – the wife of the real Don Draper, the dude whose identity Don (or Dick Whitman, anyway) stole after coming home from Korea – is the only woman on this list who truly loved Don unconditionally. I mean, that’s pretty amazing given that Don fucking stole her dead husband’s identity. But Don took care of her, and he seemed to actually love her too, in that purely platonic, fiercely loyal sort of way. It may not have been romance, but Anna Draper is the best woman ever to be in Don’s life. So why isn’t she number one? Well…

1. Roger Sterling

Roger Sterling is Don’s true life-partner and I won’t hear any arguments to the contrary. It’s an epic bromance spanning decades, fights, betrayals, ruined lives, messy breakups, alcoholism, heart attacks and god only knows what else. I guarantee you that years after the events of Mad Men, you would find these two chilling in Florida together, half-drunk divorced a dozen times over retirees popping blood-pressure meds like candy and scamming on women. They’re both too fucked up to be with anyone else, and that’s why they were made for each other. Roger Sterling is Don Draper’s one true love and you all know it.