Every Woman Don Draper’s Hooked Up With on ‘Mad Men’

One utterly confounding and intriguing question lies at the very heart of 'Mad Men': How many women can one married man sleep with over the course of 92 hour-long episodes?

Mad Men, the ambitious, award-winning AMC series, is embarking upon its seventh and final season this Sunday. Throughout its epic run, Mad Men has attempted to answer a myriad of fascinating and complex questions. They include: what is the American Dream? What does it mean to be a man? Can anyone ever be truly happy?

But one utterly confounding and intriguing question lies at the very heart of the series: How many women can one married man sleep with over the course of 92 hour-long episodes?

According to our count, the current number stands at over a dozen—and we still have all of Season 7 to go. Don Draper’s gone through two wives, a schoolteacher, a neighbor, a prostitute, and a handful of blondes. He’s slept with religious Jews and devout Catholics, young single women and unhappy wives. But all of these dissimilar women have one thing in common: a major axe to grind with TV’s most heartless lothario.

Betty Draper Francis (January Jones)

Betty Draper burst onto the small screen with an undeniable presence befitting the wife of the enigmatic Don Draper. Like Don, Betty is beautiful, cruel, and impossible to ignore. She’s also deeply unhappy—but while Don’s unhappiness stems from his constant need for reinvention, Betty is forever trapped within the identity of the model American housewife—consequentially her boredom and appetite for destruction know no bounds.

Don seduced and married Betty when she was a young model working in New York City. Refined, elegant, and to the manor born, Betty is everything that Don is not. With her good looks and endless charm, Betty completed the portrait that Don was drawing of himself: the successful American man and his gorgeous, prim suburban wife.

Of course, Betty and Don are not the perfect cookie cutter humans they so desperately wish to be seen as. In many ways, they’re extremely similar people: they both harbor severe sexual ennui, emotional unavailability, and dissatisfaction with the American dream—and they both look good doing it. They’re also both huge jerks, a fact that Betty proves time and time again between slapping neighbors, ignoring her children, and generally giving no fucks. Despite their apparent similarities, Don and Betty were a truly horrible couple, and no one was surprised when, after a string of infidelities and deceptions, Betty finally up and left her husband. In true Betty fashion, she then gets together with politician Henry Francis and has the last laugh by accomplishing something that Don never will: a happy, fulfilling marriage.

Midge Daniels (Rosemarie DeWitt)

Through Midge we first learn that Don likes to lose himself in his mistresses, as he indulges his penchant for escapism in the far, mythical reaches of the village. Midge is an artist and a free spirit, and provides an appealing alternative to the proper, domesticated Betty (although honestly, Betty’s probably cooked about two meals and done one cycle of laundry over the course of Mad Men’s six seasons). Midge rejects Don’s invitation to elope with him to Paris, making her one of the first in a series of women on this show who actually seem to enjoy their lives, professions, and hobbies, and don’t need a man to save them. Of course, this Lean In-esque narrative gets turned on its head in season four, when a heroin-addicted Midge hunts Don down, in desperate need of cash for her next fix.

Rachel Menken (Maggie Siff)

We can’t really blame the married Don for seducing Rachel Menken—we kind of have a crush on her too. Rachel is a bold, beautiful Barnard woman, and the head of Menken’s, a major Jewish department store. She’s a difficult client who demands Don’s best creative work. Like Don, she has defied her circumstances and takes immense pride in shattering the expectations of everyone she encounters. Of course, the difference is that Rachel has actually had to surmount multiple levels of discrimination as both a woman and a Jew; meanwhile, Don is just a gorgeous, successful white guy.

Of course, Don always feels like an unwanted imposter—which drives him to seduce and ultimate discard women who he actually envies and admires. At first, Rachel resists getting romantically involved with Don, and insists that she has no need for a married man in her life. While she eventually succumbs to her attraction in a very adorable rooftop make out scene, it’s not long until she realizes how truly unavailable Don Draper will always be, and breaks off their affair with an iconic line: “This was a dalliance, a cheap affair. You don’t want to run away with me; you just want to run away.”

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Bobbie Barrett (Melinda McGraw)

While working with comedian Jimmy Barrett and his wife/manager Bobby, Don begins to feel disrespected in his business negotiations with the married duo. Naturally, he responds by sticking his hand up Bobbie Barrett’s skirt in a restaurant bathroom and threatening to ruin Jimmy—all while their partners ignorantly eat and chatter nearby. Thus begins Bobbie and Don’s affair.

This arresting scene marks the beginning of a recurring Mad Men trope of vicious, cruel sex acts—all illustrations of how Don conflates and confuses power, sex, attention, and love. Don doesn’t want Bobbie so much as he wants something out of her; their sexualized power struggle is so transparently manipulative and emotionless that it can be painful to watch. Still, Bobbie is a controlling, bold woman who knows what she’s getting into, to the point that even when Don thinks he’s pulling something on her, she’s really the one who’s getting off. The Bobbie/Don affair eventually blows up when Don learns that Bobbie is gossiping about their sex life, which presents a huge threat to Don’s carefully curated image. But the ripple effect of the affair has disastrous consequences, as Jimmy Barrett reveals Don’s infidelity to Betty at a party, resulting in Don and Betty’s first separation.

Joy (Laura Ramsey)

While Don’s previous relationships were with a collection of interesting, accomplished women, Joy’s affinity for going topless certainly set her apart from the others, earning her a unique place in Don’s, and Mad Men viewers, hearts. Don meets Joy on a California business trip in Season 2, and they embark on an extremely brief, sunny, all-encompassing affair. Despite the triviality of their short dalliance, Joy makes a strong impression as a glamorous, wealthy Californian with a Palm Springs house to die for. If nothing else, Don and Joy’s feverish love affair proved that the Mad Men writers’ room has a serious West Coast complex.

Shelly (Sunny Mabrey)

While Don Draper keeps himself pretty busy with extended, punishing emotional affairs, he still saves time for the occasional meaningless one night stand. In the first episode of Season 3 Don meets and sleeps with Shelly, a TWA stewardess aboard his flight to Baltimore. After they consummate their relationship in a hotel room, the engaged Shelly actually manages to run off faster than Don, which is practically unheard of. The only thing she leaves behind are her pin-on wings, which Don takes and then gifts to his daughter Sally, officially giving Betty a run for parent of the year.

Suzanne Farrell (Abigail Spencer)

Poor Ms. Farrell. Suzanne is a beautiful, kind schoolteacher who Don aggressively chases, dates, and then callously discards like a third place science fair project. Don falls for Ms. Farrell because she is kind to his children, and she extends this maternal instinct to their romantic relationship. As idealistic as Don is cynical, Ms. Farrell actually seems to love Don, and they develop a sweet, pseudo-domestic routine. Of course, Don ends up betraying Ms. Farrell in one of the bitterest scenes in Mad Men history. As Betty finally confronts Don on his secret identity, Ms. Farrell waits for him in a car outside of his home for hours. Eventually, the realization dons on her that their affair is over, forever. Because he’s the worst, Don doesn’t even extend Suzanne the courtesy of dropping by the car to let her know.

Candace (Erin Cummings)

Candace is a prostitute who Don pays to have sex with him while slapping him across the face. Candace and Don don’t really have an emotional connection, but their interactions help reveal a crucial component of Don’s character. For someone who has so often assumed a callous, punishing demeanor in past romantic relationships, we see that Don’s truest self is begging to be chastised, demeaned, and punished.

Bethany Van Nuys (Anna Camp)

If nothing else, Don does have fairly good, or at least interesting, taste in women. No wonder then that his relationship with Bethany, an aspiring actress, doesn’t go anywhere. Set up by Roger and his young wife Jane in Season 4, Don and Bethany go on a series of unrewarding dates. Bethany is dumb as a doornail, and seems to bore Don about as much as his high-profile clients do. Even going down on Don in a moving vehicle doesn’t really get his attention, and this strange romance quickly burns out. Sometimes you have to learn the hard way that taxicab blowjobs do not a committed relationship make.

Allison (Alexa Allemani)

Allison is Don’s kind, attentive secretary. Or she was, before he decided to sleep with her and then essentially ignore her at the office next day. Bruised by Don’s lack of affection, Allison breaks down crying at work. Later, she confronts Don and throws a cigarette dispenser at him before storming out of the office, fulfilling a universal female fantasy of throwing something hard at that guy who never called. Hurling objects at your boss might not be professional, but neither is sleeping with your devoted secretary. Once Allison huffs away, Don quietly informs Joan that he would not welcome her back as his secretary.

Dr. Faye Miller (Cara Buono)

Dr. Faye Miller is a consumer research strategist who consults for Sterling Cooper Draper Pryce. Intelligent, independent, and accomplished, Dr. Miller is the kind of woman a man like Don should be honored to sleep with—so, naturally, he has to mess it up. This affair really shows how charming and manipulative Don can be. Dr. Miller actually believes that Don is a good man who will commit himself to her—and she has a PhD! Faye and Don date pretty seriously, and he even tells her about his stolen identity. Faye is so devoted to Don that she defies her ethical code in order to put him into contact with potential new clients. Despite the seeming success of this new, grown-up relationship, Don breaks it off with Faye by informing her that he randomly proposed to his secretary. At this point in the series, you really want to go back in time and organize a lady pact to never, ever sleep with Don Draper. Just ask Dr. Faye—the sexy post-coital smoking is just clearly not worth the emotional trauma.

Megan Draper (Jessica Paré)

That aforementioned secretary is Megan, a leggy French Canadian who Don impulsively proposes to when she accompanies him and his children to California. Don makes Megan a copywriter at the agency, and she excels creatively. Their relationship is similarly successful, as they play adoring wife and husband both at work and in their new, beautiful apartment. Of course, this newly wedded bliss is doomed from the start. Eventually Megan quits her job to pursue acting, and this physical rift mirrors a widening emotional gap between the couple. Megan is eventually cast in a TV show, meaning that Don has graduated from a wife who acts like she’s in a soap opera to one who actually is. Don returns to his philandering ways, leaving Megan to quietly wonder where her husband has gone. In the final episode of Season 6, Don attempts to return to his wife and start over again, promising Megan a new beginning in Los Angeles. However, Don ends up ceding the LA office to Ted, leaving his marriage in a desperate state of disrepair.

Sylvia Rosen (Linda Cardellini)

One major impediment to Don repairing his marriage is the fact that he’s sleeping with their neighbor, Sylvia. Sylvia is a devout Catholic, and her strong sense of morality casts a shadow over their illicit affair. Additionally, Don actually likes and respects Sylvia’s husband, Arnold, who he considers a friend. While we’re not told exactly when their relationship began, we see over the course of Season 6 how serious it has become. Don is desperate for Sylvia’s affection and attention, even going so far as to command her to stay in a hotel room and wait on his every whim. When Sylvia breaks off their affair and begs Don to truly go home to Megan, he is visibly bereft. A broken Don proceeds to spend nights smoking outside of Sylvia’s door and brainstorming mad schemes to get her back. Don and Sylvia briefly reconcile and meet for an apartment rendezvous, only to be walked in on by Don’s daughter Sally, effectively ending their affair once and for all.