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Don Draper’s Women In "Mad Men" Ranked From Worst To Best

The man sure does get around…

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16. Doris (Becky Wahlstrom)

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First (and only) appearance: Season 4, Episode 6, “Waldorf Stories”
Don’s relationship status at the time: Divorced from Betty.
What made her memorable: Literally nothing. She’s a waitress whom Don meets after the CLIO Awards. Even Don doesn’t remember meeting her, and he wakes up next to her!

15. Allison (Alexa Alemanni)

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First appearance: Season 1, Episode 3, “Marriage of Figaro”
Don’s relationship status at the time: When Allison and Don hook up in Season 4, he’s divorced from Betty and regularly getting his slap on with a prostitute.
What made her memorable: She was actually a really great secretary for Don. She was loyal, smart, and discreet. Until, ya know, Don got a little too eager with the sauce and boned her. Things could have been OK, if he didn’t “smooth” it over by handing her a $100 bonus the day after along with an apology. Poor Allison, she deserved better.

14. Joy (Laura Ramsey)

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First (and only) appearance: Season 2, Episode 11, “The Jet Set”
Don’s relationship status at the time: Married to Betty.
What made her memorable: You might remember Joy most as the California girl who took Don to Palm Springs, had sex with him, and then revealed that her parents knew about the whole thing. In fact, her father walked in on them post-coital, and as a viewer, you may have vommed in your mouth a bit.

13. Bethany Van Nuys (Anna Camp)

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First appearance: Season 4, Episode 1, “Public Relations”
Don’s relationship status at the time: Freshly divorced from Betty.
What made her memorable: Bethany played coy with Don for a while, and she definitely wanted to be his next Mrs. Draper. But seeing Betty, and the kind of woman he attracted, finally made her cave in to Don. It was pretty fascinating to watch.

12. Shelly (Sunny Mabrey)

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First (and only) appearance: Season 3, Episode 1, “Out of Town”
Don’s relationship status at the time: Married to Betty, who is pregnant with their third child.
What made her memorable: Don met Shelly on a flight to Baltimore, and while they didn’t join the mile high club in-flight, they did make up for lost time after a very flirtatious dinner. Another memorable moment was when Shelly confessed she was engaged, and Don said, “I’ve been married a long time. You get plenty of chances.”

11. Alice (Amy Motta)

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First (and only) appearance: Season 4, Episode 6, “Waldorf Stories”
Don’s relationship status at the time: Divorced from Betty, and pre-Doris the waitress.
What made her memorable: After the CLIOs, Alice went down on Don while humming the “Star Spangled Banner.” God bless.

10. Suzanne Farrell (Abigail Spencer)

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First appearance: Season 3, Episode 2, “Love Among the Ruins”
Don’s relationship status at the time: Married to Betty.
What made her memorable: Miss Farrell was Sally’s teacher, initially. Then she became Don’s lover, with whom he wanted to run away. While her relationship with her epileptic brother was endearing, she wasn’t the one meant for Don, and he called it off.

9. Andrea Rhodes (Mädchen Amick)

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First (and only) appearance: Season 5, Episode 4, “Mystery Date”
Don’s relationship status at the time: Divorced from Betty, and re-married to Megan.
What made her memorable: Don runs into Andrea in an elevator, and then she reminds him of the good times they used to have… all while Megan listens in. But the thing you’re more likely to recall is Don having fever dreams about Andrea until he eventually strangles her to death. (In his dream, that is.) She’s the first woman post-Megan to even tempt Don away, and by “killing” her he shows that he’s trying to do the right thing, even if he has some darker impulses.

8. Midge Daniels (Rosemarie Dewitt)

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First appearance: Season 1, Episode 1, “Smoke Gets in Your Eyes”
Don’s relationship status at the time: Married to Betty.
What made her memorable: Oh, kooky Midge! She was the bohemian artist we all loved… until she turned to drugs and then guilted Don into giving her money for MORE drugs.

7. Bobbie Barrett (Melinda McGraw)

First appearance: Season 2, Episode 3, “The Benefactor”
Don’s relationship status at the time: Married to Betty. (Poor Betty.)
What made her memorable: Bobbie and Don get very frisky in a public hallway, and they also got in an epic car crash together. But what Bobbie told Peggy about how to make it in a man’s world is what I’ll remember her for: “You can’t be a man. Be a woman. It’s powerful business when done correctly.”

6. Sylvia Rosen (Linda Cardellini)

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First appearance: Season 6, Episode 1, “The Doorway, Part 1”
Don’s relationship status at the time: Married to Megan.
What made her memorable: This was a sad sort of romance, in that Megan viewed Sylvia as a friend, and Sylvia was cheating on her hardworking doctor husband with Don. The real icing on this crummy cake, though, was when Sally walked in on the two poist-coital. Ooops!

5. Megan Calvet/Draper (Jessica Paré)

First appearance: Season 4, Episode 2, “Christmas Comes But Once a Year”
Don’s relationship status at the time: Divorced from Betty and dating Dr. Faye Miller.
What made her memorable: Megan has evoked many different sides of Don: the “let’s get married ASAP” side, the “let’s have sex while you fake clean in your underwear” side, and most recently the “I’m going to have to cheat on you, too” side. Perhaps her most important feature when it comes to Don, though, is her ability to manipulate him, even in small ways.

4. Dr. Faye Miller (Cara Buono)

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First appearance: Season 4, Episode 2, “Christmas Comes But Once a Year”
Don’s relationship status at the time: Divorced and sleeping around a whole lot.
What made her memorable: Faye is the first woman Don can actually open up to. He tells her about switching identities, and she challenges him in a way other women hadn’t before. While Megan may have been the woman he ended up marrying, she owes a lot of the grunt work of making Don a better man to Faye. Bow down, bitches.

3. Candace (Erin Cummings)

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First appearance: Season 4, Episode 1, “Public Relations”
Don’s relationship status at the time: Divorced from Betty.
What made her memorable: Candace is the prostitute who slaps Don during sex, and then he asks her to do it “harder,” and then everyone watching died a little from happiness.

2. Rachel Menken (Maggie Siff)

First appearance: Season 1, Episode 1, “Smoke Gets in Your Eyes”
Don’s relationship status at the time: Married to Betty and also sleeping with Midge.
What made her memorable: Rachel was perhaps the first woman who really threatened Don’s marriage to Betty. That’s because she was smart, business-savvy, and classy as fuck. She and Don had a real connection, and it was pretty heartbreaking to watch her turn him down.

1. Betty Draper (January Jones)

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First appearance: Season 1, Episode 1, “Smoke Gets in Your Eyes”
Don’s relationship status at the time: Married to her, sleeping with others.
What made her memorable: In general, Betty just gives zero fucks and it’s so wonderful. Whether she’s humping a dryer, shooting her neighbor’s prized pigeons, or sucking whipped cream from a can — she is number one, always. She also slept with Don while married to her new hubby, Henry Francis, and managed not to get emotionally attached. (She’s even better than Don now, apparently.)

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