Don Draper (Jon Hamm) had 19 mistresses throughout Mad Men‘s seven seasons, not counting his three wives, making all of Don Draper’s mistresses difficult to keep up with. Mad Men was one of AMC’s prestige series that followed the lives and careers of Madison Avenue advertising executives throughout the 1960s. While the other ad men of Sterling Cooper also carried on extra-marital affairs, Donald F. Draper had the most by far. While Draper is married to Betty Hofstadt (January Jones), the character went on to have an unrivaled infidelity streak.
Despite having two kids with Betty, Don cheated on her numerous times as his advertising career took off. In Mad Men season 3, Betty, who long suspected Don’s infidelities, learned that he’s really Dick Whitman. Betty divorced Don, who then married his secretary, Megan Calvet (Jessica Pare) between seasons 4 and 5. He couldn’t stay faithful to Megan either, and despite attempts to keep his private life and work life separate, Don’s affairs were well-known within Sterling Cooper, and it’s obvious that Don had many more affairs beyond what was shown onscreen. Regardless of his offscreen affairs, there are 18 of Don Draper’s mistresses in seven seasons of Mad Men.
18 Midge Daniels
Played By Rosemarie DeWitt
Midge (Rosemarie DeWitt) is the first of Don Draper’s mistresses introduced in Mad Men‘s pilot. Midge is a bohemian artist who is a sharp contrast to the slick Madison Avenue adman. It offers him a bit of escapism from the corporate world as Midge and her friends see it as the enemy of the people.
Midge is also a swerve as audiences are initially led to believe she is Don’s significant other before the end of the first episode reveals Don has a wife, Betty, and two young children in the suburbs.
She reappears in
Mad Men
season 4 where she is married to someone else.
Don’s fling with Midge ends in season 1 when he discovers that she is in love with one of her male friends, and she refuses to go on a trip with him. She reappears in Mad Men season 4 where she is married to someone else. Sadly, Midge has become addicted to heroin by that point and Don cuts her a check as if washing his hands of her before vanishing from her life.
17 Rachel Menken
Played By Maggie Siff
Don tended to avoid mixing his affairs with his professional life, but there was one notable exception. Rachel Menken (Maggie Siff) was a Sterling Cooper client who owned a department store. Don didn’t pursue his mutual attraction to Rachel until after he ended his affair with Midge, but his fling with Rachel didn’t last long. However, Don did confess details of his life as Dick Whitman to Rachel.
She was a big part of the Mad Men cast in season 1 and he even proposes that they run away together to Los Angeles. However, she realizes he is simply running away from his life and using her as an excuse. In Mad Men season 2, Don runs into Rachel, who is now married, and in season 3, Don is sad to learn that Rachel died of leukemia.
16 Joy
Played By Laura Ramsey
While some of Don’s mistresses don’t last long, they mostly all reveal something new about his character. Joy (Laura Ramsey) is a wealthy nomad Don meets when he travels to Los Angeles in the Mad Men season 2 episode, “The Jet Set.”
Don abandons Pete Campbell (Vincent Kartheiser) and stays with Joy and her strange, aristocratic friends for a few days before he leaves to visit Anna Draper and then return to New York. Of all the Don Draper mistresses, the free-spirited Joy may have been the youngest of them all.
However, she is the one who aggressively pursues Don, much to his surprise. To add to the oddness of the brief affair, Joy’s father, Willie, is the one who introduces them and then casually walks into their room while they are in bed together where he makes reference to the fact that he is attracted to Don. It makes for a rather surreal affair.
15 Bobbie Barrett
Played By Melinda McGraw
This is another instance of Don getting his romantic pursuits mixed in with his business life. Bobbie Barrett (Melinda McGraw) is the wife and manager of comedian Jimmy Barrett (Patrick Fishler). Don meets Bobbie after Jimmy upsets the owner of his sponsor, Utz Potato Chips.
He admires her boldness as she clearly is in charge of her marriage. However, when she makes a move on him, he initially suggests he is not interested though she sees through his lie. It makes for an eventful affair for the two, which includes them getting in a car accident that requires Peggy (Elisabeth Moss) to help out and let Bobbie stay with her.
Perhaps Bobbie’s biggest contribution to the series is her advice to Peggy that she cannot win by trying to be a man in the business world but can use being a woman to her advantage. Don ends their Mad Men season 2 relationship when he learns Bobbie has been gossiping about his prowess in the bedroom.
14 Shelly
Played By Sunny Mabrey
Shelly (Sunny Mabrey) is one of the most short-lived Don Draper mistresses and seems to represent the idea that Don does this sort of thing everywhere he goes. Don has a one-night stand with the stewardess when he travels to Baltimore with Sal Romano (Bryan Blatt) in Mad Men season 3. Shelly invites Don and Sal to dinner with her flight attendant friends, but she is gone after a fire alarm evacuates the hotel.
Don is shown to be a massive hypocrite, having an affair with Shelly while on the trip but getting angry at Sal.
However, the real fallout of Don’s Baltimore trip was his discovery that Sal is a closeted homosexual, which later led to Romano’s dismissal from Sterling Cooper. In that sense, Don is shown to be a massive hypocrite, having an affair with Shelly while on the trip but getting angry at Sal for doing the same thing simply because it was with another man.
13 Suzanne Farrell
Played By Abigail Spencer
Suzanne Farrell (Abigail Spencer) is Sally’s teacher who’s the last of Don Draper’s mistresses before Betty ends their marriage. Despite her hesitation, Suzanne begins an affair with Don, after admitting to him and herself that she cannot stop thinking about him. While Don falls for her idealism, she also seems to see through him in ways other women haven’t, telling him that she sees a lot of sadness in him.
Suzanne represents someone who is a good person dragged into Don’s world of lies and deceit. She is constantly nervous about being caught in public with Don, and not enjoying their time together. Things end abruptly when Betty discovers Don’s hidden records that he was really Dick Whitman and confronts him, which immediately puts an end to Draper’s tryst with Miss Farrell. When Don calls her to call it off, she asks him if he is okay to which he responds, “Only you would ask about me right now.”
12 Candace
Played By Erin Cummings
In Mad Men season 4, Don moved out of his house with Betty and Jon Hamm’s problematic ad man took an apartment in Manhattan. Candace (Erin Cummings) is a sex worker Don frequently hires. It is a sign of him slipping further into a dark spiral with his relationships becoming purely transactional. There is also a disturbing moment between the two when Don has rough sex with Candace claiming that he thought she liked it when she objects to it.
Later in season 4, Draper introduces Lane Pryce (Jared Harris) to Candace and her friend to cheer him up when his marriage is on the rocks. They go back to Don’s apartment, but Lane notices that Candace seems to have a familiarity with the apartment, realizing that she and Don have some previous connection with each other.
11 Allison
Played By Alexa Alemanni
Allison (Alexa Alemanni) became Don’s secretary after Peggy became a copywriter, and, in turn, she became another one of Don Draper’s mistresses. Don brings her along when he leaves Sterling Cooper to co-found Sterling Cooper Draper Pryce. Allison succumbed to her attraction to Don and slept with him after the office Christmas party.
She was then heartbroken when Draper pretended like it never happened and gave her cash as a Christmas bonus. Allison is one of Don’s affairs that makes him look truly awful. She is shown to be a very effective and successful secretary for him which makes her dismissal from the office all the more telling.
In the aftermath of her leaving, Don is shown to begin writing an apology letter to her which shows that he is aware of his terrible behavior, but eventually discards it. Joan Harris (Christina Hendricks) replaced Allison with the elderly Ida Blankenship (Randee Heller), a sign that Don cannot be trusted to not make the same mistake again.
10 Bethany Van Nuys
Played By Anna Camp
Bethany Van Nuys (Anna Camp) is a friend of Roger Sterling’s young bride Jane (Peyton List) with whom Don is set up. It is also noted that she bears a striking resemblance to Don’s ex-wife Betty. Despite her youth and charms, of all the Don Draper mistresses, Don doesn’t have much chemistry with Bethany.
While he admits she is a sweet girl, he shows little interest in her, taking her on only a few dates over the course of several months. However, Bethany on his arm does make a couple of key people in Don’s life jealous: Ted Chaough (Kevin Rahm) and his wife run into Don and Bethany at Benihana’s, and later, Betty is furious when she finds herself at the same restaurant as Don and Bethany.
In the end, Don writes about Bethany in his journal, lamenting that he knows who she is by this point, and it is not the person he wanted her to be.
9 Alice & Doris
Played By Amy Motta & Becky Wahlstrom
The combination of two very brief affairs with two different women are used to show the further spiraling nature of Don’s behavior. When Don wins a Clio Award in Mad Men season 4’s “Waldorf Stories,” he goes on a bender that lasts for days. Don goes to bed with Alice (Amy Motta), a woman he picks up at a bar while he’s celebrating his Clio.
However, when he wakes up in the morning, he is next to a waitress named Doris (Becky Wahlstrom), whom he doesn’t recognize. Worse, Doris calls him “Dick,” which means he drunkenly calls himself by his secret birth name and not his carefully maintained identity during his blackout tryst with the waitress. In a quick moment with these two women, the show highlights the destructive path Don is on. While he is always reckless, this is a rare instance in which he recognizes it himself.
8 Dr. Faye Miller
Played By Cara Buono
Miller is a consultant for a consumer research company working with Sterling Cooper Draper Pryce in
Mad Men
season 4.
Dr. Faye Miller (Cara Buono) is one of the smartest Don Draper mistresses. Miller is a consultant for a consumer research company working with Sterling Cooper Draper Pryce in Mad Men season 4. They do not get off to a great start, as Don is unwelcoming and unconvinced of the importance of Faye’s work.
However, when they start to develop more of a professional relationship, Don becomes interested in moving it into unprofessional territory. Faye is initially skeptical about Don’s advances, but he reveals the truth about his past as Dick Whitman when Draper has a panic attack about his identity theft and desertion being discovered by the U.S. government.
Don ends the relationship after he proposes to Megan, and a heartbroken Faye tells him that she hopes his fiancée knows that Don “only likes the beginnings of things.”
7 Andrea Rhodes
Played By Mädchen Amick
While Don Draper has a lot of dark sides to him, he does seem to avoid confronting his problematic relationship with women. He has an affair with no remorse, but there are some moments that suggest there is an underlying guilt that he refuses to address opening. One example of this comes in the season 5 episode of Mad Men, “Mystery Date.”
The newlywed Don and Megan run into Andrea Rhodes (Mädchen Amick) in the elevator in Mad Men season 5. From Andrea’s relentless flirting with Don, it’s clear that she was one of the previously unseen Don Draper mistresses. When Don is feverishly ill, Andrea enters his apartment and attempts to sleep with him.
Don chokes her to death and hides her body under the bed. It turned out to be only a dream, but Don “killing” Andrea was one of Mad Men‘s most odd and disturbing moments. It also suggests that these affairs and his relationships with women are secrets he wants to bury deep down to never be revealed.
6 Sylvia Rosen
Played By Linda Cardinelli
Among the many mistresses, there were some Don Draper may have loved if he was capable, and there is a sense that Sylvia was one of them. Don surprisingly didn’t have any known affairs during the early part of his marriage to Megan in Mad Men season 5, but by season 6, Draper is back to his old tricks — and with his neighbor too. Sylvia Rosen (Linda Cardinelli) is the wife of Don’s friend Dr. Arthur Rosen (Brian Markinson).
Don and Sylvia carry on their affair under Megan and Arthur’s noses, however, she is also a friend of Megan’s and breaks it off when the guilt gets to be too much. This leads to Don becoming obsessive about how he could get her back. When Don uses his influence to help Sylvia’s son avoid Vietnam, she falls back into bed with him only for Sally to accidentally walk in on her father having sex with his neighbor, which immediately puts an end to it.
5 Lee Cabot
Played By Neve Campbell
Scream‘s Neve Campbell is one of the biggest names to guest star on Mad Men, appearing in only one episode with a very interesting storyline with Don. Technically, Lee Cabot (Campbell) isn’t one of Don Draper’s mistresses and Don didn’t have an affair with her. The two meet on a red-eye flight from LA to New York in Mad Men‘s season 7 premiere.
Draper is clearly attracted to Lee, a wealthy widow, and they share an intimate plane ride home, but Don turns down her invitation to “share a cab” with Lee when they land in New York. There is an interesting connection that develops between the two in a short span of time.
They are both vulnerable and share an emotional intimacy that is stranger than many of Don’s actual affairs. Mad Men loves examining the reality of fleeting relationships with people coming in and out of each other’s lives and Lee makes for one more memorable addition to such a story.
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4 Amy
Played By Jenny Wade
Part of what makes Don such an unlikable character is because of the deceitfulness of all his affairs. It is not just how he treats the women he sleeps with as disposable, but how he disrespects his wives at the same time. Throughout much of the series, Betty and Megan are unaware of his affairs. However, this is one instance in which Don at least isn’t sneaking behind anyone’s back.
Amy (Jenny Wade) is one of Megan’s friends in California after she left New York and moved to the West Coast to pursue her acting career in Hollywood. After a party at Megan’s house, Don’s estranged wife invites him to have a three-way with her and Amy. However, there is a sadness to it as if Megan is attempting to make Don feel as though he is happy with her by giving him this fantasy and trying to offer him what he wanted in their marriage.
3 Tricia
Played By Kirstin Ford
Tricia (Kirstin Ford) is not only one of the many Don Draper mistresses, but yet another stewardess Don became acquainted with when he flew to LA on weekends to visit Megan in Mad Men season 7. However, she is an example of how Don is willing to pursue these flings a little longer in a casual way rather than just making them one-night stands. When Tricia is introduced on the plane, it is established that they know each other thanks to Don’s frequent travels.
Despite the fact that Don tells her he is traveling to see his wife, Tricia calls Don’s answer service while she is on a layover and asks to meet up. They go to his apartment, where she accidentally spills wine on his white rug. In a sign of his immense wealth and that he doesn’t care for this apartment his wife furnished, he decides to have sex with Tricia on the rug.
2 Diana Bauer
Played By Elizabeth Reaser
While out on the town with some female companions and just before getting the call from Tricia for their impromptu liaison, Don becomes fixated with a waitress at a diner whom Draper thinks he met before. The waitress’ name is Diana Bauer (Elizabeth Reaser) and she turns out to be a desperately sad woman who abandoned her son in the Midwest. When she vanishes, Don drives to Wisconsin to try to find her.
The fact that she was a woman ashamed of her past and trying to outrun it clearly struck a chord with Don as he has been doing a similar thing for most of his life.
As Mad Men‘s ending drew near, Diana was an odd affair for Don to fixate on, but she provided some of the impetus for Draper to leave New York heading towards the series finale. The fact that she was a woman ashamed of her past and trying to outrun it clearly struck a chord with Don as he has been doing a similar thing for most of his life.
1 Eve
Played By Fiona Gubelmann
Eve (Fiona Gubelmann) was the last of Don Draper’s mistresses in Mad Men‘s series finale. As Don makes his way to California, he spends time racing cars, and Eve is the local woman he meets and sleeps with. She tries to steal his wallet, but when she is caught, she is not apologetic. Don gives her the money anyway, insisting that he would have if she asked, and she thanks him for it.
No doubt, Don continued having affairs after Mad Men ended, especially if he returned to New York to resume his advertising career. However, this is an interesting final one on the way to Don’s self-discovery in the final moments of the series. To Eve, he was a rich mark to get some money from while he was on his way to separate himself from such an identity. In the end, she helped solidify that changing is not so easy for Don.
Which Of His Mistresses Should Don Have Ended Up With
Don Draper wasn’t lacking when it came to extramarital affairs. Affairs never solved his problems, though, and most of these women ended up better for it when Don didn’t reenter their lives. Nevertheless, Sally’s teacher, Suzanne Farrell, may have been the right choice for the ad executive, as she was one of the more innocent and seemed to have legitimate feelings for Don. Not only that, but it was those qualities that Don liked, suggesting he might have seen how right for him she was.
Rachel Menken was another mistress that may have had a real chance with him. Despite their affair being short-lived, the two had obvious chemistry, and Don was honest with her about his true identity. Don even dreams of her just before learning of her death. However, none of these women were really a long-term option, and Don Draper in Mad Men often reaped the consequences of his actions.
How Did Don Draper’s Affairs Impact His Life
Assessing how Don Draper’s mistresses and perpetual infidelity impacted his life is one of the most interesting aspects of the Mad Men character. There are two sides to the coin, because on the one hand they caused him a significant amount of distress, but on the other, they weren’t the setback to his goals and ambitions they could have been.
Don Draper’s affairs clearly had a significant impact on his mental state. This was all too apparent when he had a dream about killing Angela. For Don, engaging in extramarital affairs and casual problematic sexual encounters is a more-or-less compulsive behavior. It’s unlikely Don could stop even if he wanted to, and there are plenty of moments when he shows glimmers of self-awareness around this.
What’s more, Don is a man who is constantly running from the secrets of his past. This started from the moment stopped being Dick Whitman and stole the Don Draper identity. This need to constantly be on guard lest the past return to haunt him causes him no shortage of anxiety. Every affair Don Draper has compounds this — and the impact is often made worse due to the fact that multiple mistresses he has throughout Mad Men create a risk of his peers discovering that he is, in fact, Dick Whitman.
However, it can also be said that Don Draper’s affairs didn’t impact his life anywhere near as much as they should. Yes, his infidelity eventually led to Betty divorcing him, and several of his affairs caused friction between Don and many of his friends. However, 19 is a pretty big number when it comes to how many affairs a person has had, and almost 20 showed on Mad Men are implied to simply be the tip of the iceberg.
Despite constantly risking his career, friendships, and his carefully-cultivated life after deciding not to be Dick Whitman anymore, Don Draper’s affairs never fully wreck his life. Considering how many he’s had, this is a pretty mind-blowing realization — even more so when factoring in how many of these encounters were with women linked to his professional life. Ultimately, Mad Men didn’t shy away from the fact that Don Draper’s attitude towards sex created problems, but it was also unrealistic in many ways when it came to the lack of actual consequences.
