Every Woman Don Draper Has Slept With on 'Mad Men' – So Far

by Lisa Liebman 7:50 AM PDT, April 03, 2015
Photo: AMC

Mad Men’s Don Draper has used his impossibly good looks and charm on more women than any one (mostly) married man has the right. For seven seasons, we’ve watched him hook up with an artist, teacher, businesswoman, psychologist, several secretaries, even the occasional slap-happy hooker. Some of them he’s even loved.

As the show begins its final seven episodes on April 5, we’ve made our own version of Draper’s little black book -- a complete list of all the lothario’s ladies, or at least all those we’ve seen him with on-screen.

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Aimee (Megan Ferguson)
Don’s sexual issues make slightly more sense when you take into account where they started: Dick Whitman (Draper’s original identity) is “a whore’s child,” as his stepmother liked to remind him, who lost his virginity as a terrified teenager to Aimee, a prostitute in his uncle’s brothel. The fact that Aimee then bragged about how she “took that boy's cherry for five dollars,” resulting in him getting beaten up, explains a lot.

Photo: AMC

Betty Francis, formerly Betty Draper (January Jones)
Don sweeps his model first wife off her feet, believing she’ll help him create the picture-perfect life Dick Whitman aspires to. But as we all know, looks can be deceiving, and Betty’s gorgeous exterior belies the ice queen beneath. She’s as cruel, manipulative, and withholding as her husband (not to mention a neglectful mother). When she discovers Don’s duplicity, she becomes even less inclined to forgive him, despite all his success, ultimately leaving him for the older, more stable politician Henry Francis. Still, there’s no denying their sexual spark, which is reignited years later when they reconnect while visiting Bobby at camp. “You’re as beautiful as the day I met you,” he tells her, admitting later in bed that he misses her. “That poor girl,” Betty says of Don’s second wife, Megan. “She doesn’t know that loving you is the worst way to get to you.”

Midge Daniels (Rosemarie DeWitt)
Midge is the first lover of Don’s we meet in the pilot, even before we learn Don’s a married man. She’s the anti-Betty, a bohemian artist who doesn’t want to be domesticated, throwing a TV set he’s gifted her out the window of her Greenwich Village apartment and eventually turning down his marriage proposal. “You think I’d make a good ex-wife?” she asks. Years later, she turns up addicted to heroin and Don takes pity on her and buys one of her paintings.

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Rachel Menken (Maggie Siff)
The no-nonsense, sophisticated Jewish department store heiress demands Don up his game if he wants her business. An early challenge to his ideas of a woman’s place in the world, naturally, he tries to seduce her! Though Rachel initially rebuffs him, she ultimately succumbs. But their relationship ends soon after he asks her to run away with him to Los Angeles. “This was a dalliance, a cheap affair,” she replies. “You don’t want to run away with me; you just want to run away. You’re a coward!”

Photo: AMC

Bobbie Barrett (Melinda McGraw)
Sterling Cooper’s hiring of comedian Jimmy Barrett for an Utz potato chip commercial turns into a package deal with his tough-talking manager/wife Bobbie along for the ride. When Jimmy insults the Utz owner’s wife, Don tries to do damage control with Bobbie, but she puts the moves on him, suggesting Jimmy will apologize if he knows “he's got a shot at your wife.” Later at the apology dinner, she tries to shake Don down for $25,000 in the ladies’ room. His response: grabbing her and putting his hand up her skirt, and threatening to ruin Jimmy if he doesn't apologize before the main course. Later, Peggy will rescue them when they get into a drunk-driving accident, and Jimmy will retaliate by telling Betty about Don’s affair with Bobbie, leading to the Drapers’ first separation.

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Joy (Laura Ramsey)
On a California business trip, Don meets Joy, a glamorous dilettante introduced to him by a European count at a poolside hotel bar. “Why would you deny yourself something you want?" she asks Don, when she runs into him the next day, after he’s turned down the count’s dinner invitation. Joy ultimately gets Don to a friend’s Palm Springs house, where she spends much of the time topless — and Don learns the count is her father!

Photo: AMC

Shelly (Sunny Mabrey)
On yet another business trip, this time to Baltimore with art director Sal, Don meets Shelly, a flirtatious and engaged stewardess who happens to be staying at the same hotel as the ad men. Their tryst is interrupted by the hotel’s fire alarm. Don gives his daughter Shelly’s airline pin.

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Photo: AMC

Suzanne Farrell (Abigail Spencer)
Don and a very-pregnant Betty first meet Suzanne at a parent-teacher conference when Sally acts out after Betty’s dad has died. After an early-morning drive to work when Don sees her out jogging, their attraction turns into a full-blown affair. At first Suzanne says she doesn’t care that he’s married, but later she laments the fact they can never be seen in public. “I just wanted more than I thought I would want,” she tells him. “But it'll pass.” Don cruelly leaves her in his car outside his house as Betty confronts him about his true identity.

Candace (Erin Cummings)
Don spends his first post-divorce Thanksgiving at his new apartment with Candace, a prostitute whom he pays to slap him around. “Harder,” he demands. Later, he and account man Lane will hook up with her and her friend Janine at a nightclub.

Allison (Alexa Alemanni)
Don’s faithful secretary’s duties go from business to pleasure when Don drunkenly leaves his keys at the office after a Christmas party and Allison delivers them to his door. “My goodness,” she giggles after they do it. The next day, it’s back to business for Don. But try as she might to remain professional, Allison soon loses it during a focus group where the secretaries talk about their love lives as Don looks on. “He turns on the charm and then yanks it away,” she later confides to Peggy before resigning. When she asks Don for a recommendation, he tells her to write it herself, and he’ll sign it. So she throws a paperweight at him!

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Bethany Van Nuys (Anna Camp)
Roger sets Don up on a blind date with Bethany, a dumb-blonde actress who can’t even keep his interest when she’s going down on him in a taxicab. “She wants me to know her, but I already do,” he later writes dramatically in the journal he’s started keeping. He also knows the effect she’ll likely have on Betty after they unexpectedly run into her and Henry.

Alice (Amy Motta) and Doris (Becky Wahlstrom)
Don ties one on at the 1965 Clio advertising awards ceremony, taking home a statuette and Alice, who’s sized him up at the bar and asked Roger whether he’s single. The next day, he awakens to a ringing phone — beside a completely different woman. Betty’s called to say he’s missed his day with the kids. “I’m coming on Sunday,” he tells her. “It is Sunday,” she hisses. He also learns the woman in his bed is a waitress named Doris, and she knows him as “Dick.”

Photo: AMC

Dr. Faye Miller (Cara Buono)
A consumer-research analyst consulting for the Sterling Cooper Draper Price, Dr. Faye is the total package: smart, beautiful, independent and no pushover. But Don likes a challenge, so even the woman with a Ph.D. eventually falls for him. It’s a tad Freudian: Don reminds her of her father, “a handsome two-bit gangster like you.” Don does let his guard down with her, revealing his true identity. And she goes against her ethics, setting up a meeting for him with Heinz, because she knows they’re unhappy with their agency. Just as her company severs ties with Don’s and they can date openly, Don jets off to California, returning infatuated with his new secretary, Megan. When he finally tells Faye he’s getting married, she says she hopes Megan knows he only likes “the beginnings of things.”

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Photo: AMC

Megan Calvet Draper (Jessica Paré)
Mrs. Blankenship’s replacement (after she died at her desk) is would-be actress Megan, who gets up close and personal with Don after he offers to double her salary, if she’ll accompany him on a California business trip and look after his kids. Soon the man who admitted to Faye who he really was admits that Megan knows nothing about him. “You have a good heart,” she responds, “and I know that you're always trying to be better.” (Yeah, that’s what they all think at the beginning.) Back in New York, he pops the question, and they settle into a swank Park Avenue penthouse. Soon Megan quits her job and carves out a career as a soap-opera actress. And it’s back to adultery as usual for Don. Later, Megan will confess to Sylvia Rosen, the neighbor with whom Don is carrying on right under her nose, that she’s had a miscarriage -- before telling Don. Ultimately, the gulf between them grows into a physical one, with Megan moving to L.A. to pursue acting, while Don pretends to be employed in New York. Their marriage never quite recovers, though Don tells her he’ll always take care of her: “I owe you that.” Megan replies tearfully, “You don’t owe me anything.”

Andrea Rhodes (Mädchen Amick)
Don runs into Andrea, a former lover, with Megan in the elevator on the way into work. After he goes home sick, she shows up at his door. He sends her away only to seemingly awaken later to find her in his bedroom. Though he initially protests, he unzips her dress and is next seen in bed with her, telling her it was a mistake. “You loved it,” she replies. He knocks her to the floor and chokes her to death, shoving her body under the bed. The next morning, Megan brings him breakfast with no sign of Andrea – and Megan says she’s been with him all night.

Photo: AMC

Sylvia Rosen (Linda Cardellini)
 Nothing like having a downstairs neighbor who’ll turn you on to Dante’s Inferno and sneak around to fulfill all your sexual kinks. Sylvia somehow maintains the image of good Catholic wife to heart surgeon Arnold Rosen while simultaneously trysting with Don in her apartment and at a hotel where he abandons her, commanding her not to leave. Later he’ll call to tell her not to answer the phone, call back to see if she complies, and send a red dress from Saks Fifth Avenue as a reward. He’ll also return, leave for a business trip, and return again (“You exist in this room for my pleasure”) only to have Sylvia tell him it’s over. But when her son needs help avoiding the draft, guess who helps? It’s only when Sally discovers the two of them in flagrante delicto that their affair is truly over.

Amy (Jenny Wade)
While Don is in LA to help out Anna Draper’s pregnant niece, the increasingly independent Megan sets up a menage a trois with her friend Amy. “I’m supposed to tuck you in,” Amy says to him. Megan tells him to kiss her before quickly joining in.

Mad Men returns for the final seven episodes Sunday, April 5 at 10 p.m. ET/PT on AMC.

What will the Mad Men stars miss the most? Watch Jon Hamm, January Jones and their co-stars dish to ET in the video below as they prepare to say goodbye!