Every Woman Don Draper Has Slept With on 'Mad Men'

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.

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. 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.

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, eventually turning down his marriage proposal. "You think I’d make a good ex-wife?" she asks.

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.

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."

On a California business trip, Don meets Joy, a glamorous dilettante introduced to him by a European count at a poolside hotel bar. 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!

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 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.

Don spends his first post-divorce Thanksgiving at his new apartment with Candace, a prostitute whom he pays to slap him around. Later, he and account man Lane hook up with her and her friend Janine at a nightclub.

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. 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.

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.

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."

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. 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."

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. Back in New York, he pops the question, and they settle into a swank Park Avenue penthouse.

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. Though he initially protests, he unzips her dress and is next seen in bed with her, telling her it was a mistake. 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.

Nothing like having a downstairs neighbor who’ll turn you on to Dante’s Inferno and sneak around to fulfill all your sexual kinks. It’s only when Sally discovers the two of them in flagrante delicto that their affair is truly over.

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.

Don first meets Diana, a waitress with a dog-eared copy of John dos Passos in her apron pocket, when Roger drops a $100 bill on an $11 tab, hoping to impress the ladies the ad men are entertaining. When Don returns alone, Diana has sex with him in the alley, then immediately dismisses his interest, thinking he's simply collecting on the generous tip.