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The Complete Ranking of Every Woman Don Draper’s Slept With on ‘Mad Men’

The Complete Ranking of Every Woman Don Draper’s Slept With on ‘Mad Men’: AMC

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While the quote, “Women want to be with him, men want to be him,” was originally meant to describe James Bond, it seems to be a far better comparison to Mad Men’s Don Draper (played by the masterful Jon Hamm, who somehow hasn’t won an Emmy for this role). His life is basically wake up, put on a kickass suit, make a ton of money, drink enough scotch to kill a grizzly bear then have sex with the hottest woman he can find. It’s basically how every male who attends an Ivy League university envisions his life will be like after graduation.

While Draper has bed many women over the course of the show, the quality of his “lady friends” has fluctuated over the course of the show. In honor last night’s premiere of the final half season of the show, here is an entirely unscientific and subjective ranking of every woman Don Draper has slept with over the course of the first seven seasons. (Some spoilers below.)


20. Amy (Jenny Wade)
Season 7

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We really know nothing about Amy other than she’s the woman who allowed herself to be in a threesome with Don and Megan. And while you’d think that would deserve a higher ranking, can you name anything else about her other than she was in a threesome? Hell, did you even know her name was Amy?

19. Doris (Becky Wahlstrom)
Season 4

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It was a funny gag when Don woke up after the CLIO awards to find Doris (and not a woman later on this list) in his bed. But clearly she didn’t do anything to make herself memorable to Don. Then again, this is a man who spends his life blackout drunk half the time, so maybe it’s slightly understandable.

18. Midge Daniels (Rosemarie Dewitt)
Season 1

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Of all the actual girlfriends who Don has had over the years, Midge remains the least remarkable. Yeah, she’s an artist and a free spirit who is supposed to represent the Yin to Don’s Yang, but she’s really not that interesting. And then she becomes a heroin junkie.

17. Andrea Rhodes (Mädchen Amick)
Season 5

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Technically, we don’t know for a fact that Andrea and Don ever slept together other than in his fever dream where he chokes her to death. But it’s certainly implied in their flirtatious elevator encounter. We’re guessing it didn’t go well, considering he has a fantasy about murdering her. And for a guy who can’t keep it in his pants, Don keeps remarkable self-control not to pursue her after their heated elevator moment.

16. Tricia from TWA (Kirstin Ford)
Season 7

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If you watched last night’s premiere, you’ll know Tricia as the girl who spilled wine on Don’s bedroom carpet. But if you do some sleuthing, you find out that Tricia originally appeared in episode 3 of Season 7 as a flight attendant that Don flirts. And then they brought her back in the premiere last night! Is this the first ever Mad Men easter egg?

15. Bethany Van Nuys (Anna Camp)
Season 4

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Bethany seems nice, but we can understand why Don didn’t want to pursue her. She’s basically just rip-off Betty. Why order the hamburger when you can get the steak instead?

14. Bobbie Barrett (Melinda McGraw)
Season 2

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Are we docking Bobbie Barrett points for being married to Jimmy, the most insufferable character during the entire series of Mad Men? Yes, yes we are.

13. Allison (Alexa Alemanni)
Season 4

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Although Allison appeared on-and-off the first three seasons, it wasn’t until season 4 when she became Don’s secretary that she really made her mark. After a one-night tryst, he rejects her and pretends it never happened. Don’s treatment of Allison is one of the first times in the show where you think, “Maybe Don Draper is really a huge asshole.”

12. Diana (Elizabeth Reaser)
Season 7

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Another woman from last night’s season premiere, Diana was the waitress Don banged in the alley after he and Roger left her a $100 tip the night before. She’s probably the first and only woman on this list who both had sex with Don and wants nothing to do with him.

11. Candace (Erin Cummings)
Season 4

In the season 4 premiere, Don hires a prostitute and brings her back to his apartment. As they’re about to get it on, Don asks her to slap him. She does. And then he asks her to do it harder. This is when millions of men realized they probably shouldn’t idolize this man.

10. Aimee Swenson (Megan Ferguson)
Season 6

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Aimee deserves distinction for being the woman to take Don’s virginity. He was also a kid, so she’s sort of a pedophile. But if the 1960s were a different time, then the 1930s were a very different time. We have very mixed emotions about her.

9. Joy (Laura Ramsey)
Season 2

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Don decides to take a vacation to California, where he meets up with Joy and her group of wondering weirdos. Where every other woman on this list spends her time trying to figure Don out, she’s the only one that he’s confused by. There’s also a very interesting show involving Joy flying country to country having sex with strangers that should definitely get a spin-off.

8. Shelly (Sunny Mabrey)
Season 3

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Shelly herself isn’t very memorable. But her interaction with Don is. After telling him she’s engaged, he replies, “I’ve been married a long time. You get plenty of chances.” Jesus, Don…

7. Rachel Menken (Maggie Siff)
Season 1

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Rachel’s problem is similar to Midge’s. She’s basically written in as Betty’s opposite. And while there’s a strong bond between her and Don, we knew their personalities were going to clash. Also she really thinks her department store is a lot classier than it is. (Author’s note: I wrote this before it was revealed Rachel died in last night’s premiere. It still doesn’t really change the way I feel about her.)

6. Alice (Amy Motta)
Season 4

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When she started humming the “Star Spangled Banner” while going down on Don, men watching the show suddenly became far more patriotic.

5. Sylvia Rosen (Linda Cardellini)
Season 6

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Sylvia is one of the most tragic characters on this show. She loves her husband and wants to push Don away, but keeps worming himself in. He gets her son out of the draft just so he can bang her! While Don treated a lot of women on this list poorly, Sylvia is definitely one of the more slighted.

4. Suzanne Ferrell (Abigail Spencer)
Season 3

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Don always wanted his wife to be the perfect mother to his children, the one he never had. Suzanne represented everything Don wanted in a woman, but he knew he couldn’t be the husband she needed and called it off. It’s probably the one time Don ended a relationship for altruistic reasons.

3. Megan Draper (Jessica Paré)
Season 4-7

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Megan secretly knew how to play Don. She convinced him to let her try acting. She moved to Los Angeles without him. And she did so without totally pure intentions. She truly loved Don and wanted to change him, but he wouldn’t budge. We still don’t know how their relationship ends, but we don’t think it will be happy.

2. Dr. Faye Miller (Cara Buono)
Season 4

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Faye is the biggest victim of Don Draper. He’s the first woman he willingly tells about his fake identity. She helps him become a better father and stops his slide into full-blown alcoholism. She challenges Don in ways no other woman could. And then he marries Megan. We love Megan, but he should’ve been with Faye.

1. Betty Draper (January Jones)
Season 1-3

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Betty could never be who Don wanted her to be. She tried and tried and tried, but he was impossible to please. The show was never better than the first three seasons as Betty and Don’s relationship continually unraveled until she finally decided to end it all. While the last few seasons haven’t used Betty as effectively, she’s what made this show so memorable and one of the greatest of all-time.

Why does this show have to end?


Joseph Misulonas is an editorial assistant for Playboy.com. He can be found on Twitter at @jmisulonas.

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