All 18 of Don Draper’s mistresses explained

Don Draper (Jon Hamm) has 19 mistresses Crazy peoples seven seasons, not counting his three wives, making all of Don Draper’s mistresses difficult to keep up with. Crazy people was one of AMC’s prestige series that followed the lives and careers of Madison Avenue advertising executives throughout the 1960s. While Sterling Cooper’s other ad men also had extramarital affairs, Donald F. Draper had the most by far. While Draper is married to Betty Hofstadt (January Jones), the character has an unrivaled infidelity streak.

Despite having two children with Betty, Don cheated on her many times as his advertising career took off. in Crazy people In season 3, Betty, who has long suspected Don’s infidelities, learns that he is really Dick Whitman. Betty divorced Don, who was then married to his secretary, Megan Calvet (Jessica Pare) between seasons 4 and 5. He also failed to remain faithful to Megan, and despite attempts to maintain his private and work life Separately, Don’s issues are well-known in Sterling Cooper, and it is obvious that Don has many more issues beyond what is shown on screen. Regardless of his offscreen affairs, there are 18 of Don Draper’s mistresses in seven seasons of Crazy people.

18

Midge Daniels

Played by Rosemarie DeWitt

Midge (Rosemary DeWitt) is The first of Don Draper’s mistresses introduced in Crazy peoples pilot. Midge is a bohemian artist who is a sharp contrast to the glitzy Madison Avenue admin. 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 that Don has a wife, Betty, and two young children in the suburbs.

She appears again Crazy people 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 wants to go on a trip with him. She appears again Crazy people Season 4 where she is married to someone else. Unfortunately, Midge has become addicted to heroin by this point and Don cuts her a check as if to wash his hands before he disappears 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 develop his mutual attraction to Rachel until after he ended his affair with Midge, but his fling with Rachel didn’t last long. However, Don confessed details of his life as Dick Whitman to Rachel.

She was a big part of the US Crazy people Throw in season 1 and he even suggests they run away together to Los Angeles. However, she realizes that he is simply running away from his life and using her as an excuse. in Crazy people In season 2, Don runs into Rachel, who is now married, and in season 3, Don is saddened to learn that Rachel has died of leukemia.

16

joy

Played by Laura Ramsey

Although 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 Crazy people Season 2 episode, “The Jet Set.”

Don leaves Pete Campbell (Vincent Kartheiser) and stays with Joy and her strange, aristocratic friends for a few days before leaving to visit Anna Draper and then returning to New York. Of all the Don Draper mistresses, the free-spirited Joy might be the youngest of them all.

However, she is the one who aggressively pursues Don, much to his surprise. To add to the strangeness of the brief affair, Joy’s father, Willy, is the one who introduces them and then casually walks into their room while they are in bed together, where he refers to the fact that he is attracted to Dawn . It makes for quite a surreal affair.

15

Bobby Barrett

Played by Melinda McGraw

This is another example of Don getting his romantic pursuits mixed up with his business life. Bobbie Barrett (Melinda McGraw) is the wife and manager of comedian Jimmy Barrett (Patrick Fishler).. Don meets Bobby after Jimmy upsets the owner of his patron, Utz Potato Chips.

He admires her courage as she is clearly in charge of her marriage. However, when she makes a move on him, he initially suggests he’s not interested even though she sees through his lie. It makes for an eventful affair for the two, which includes them getting into a car accident that requires Peggy (Elisabeth Moss) to help and let Bobby stay with her.

Perhaps Bobby’s biggest contribution to the series is her advice to Peggy that she can’t win by trying to be a man in the business world but can use being a woman to her advantage. This ends very well Crazy people Season 2 relationship when he learns that Bobby has been gossiping about his violence in the bedroom.

14

Shelly

Played by Sunny Mabry

Shelly (Sunny Mabry) is one of Don Draper’s most short-lived 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 Crazy people Season 3. Shelly invites Don and Sal to dinner with her flight attendant friends, but she’s gone after a fire alarm evacuates the hotel.

Don is shown to be a massive target who has an affair with Shelly while on the trip, but he is angry with Sal.

However, the real fallout from Don’s Baltimore trip was his discovery that Sal is a closeted homosexual, which later led to Romano’s dismissal of Sterling Cooper. In this sense, Don is shown to be a massive target, having an affair with Shelly while on the trip, but resenting Sal for doing the same thing simply because it was with another man.

13

Susan Farl

Played by Abigail Spencer

Suzanne Farrell (Abigail Spencer) is Sally’s teacher Who is the last of Don Draper’s mistresses before Betty ends their marriage. Despite her hesitation, Susan begins an affair with Don, after admitting to him and herself that she can’t stop thinking about him. While Don falls for her idealism, she also seems to see through him in ways other women don’t, telling him that she sees a lot of sadness in him.

Susan 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 doesn’t enjoy their time together. Things end abruptly when Betty discovers Don’s hidden records that he is really Dick Whitman and confronts him, which immediately puts an end to Draper’s comfort with Miss Farrell. When Don tells her to call it off, she asks him if he’s okay to which he responds, “Only you would ask about me now.”

12

Candace

Played by Erin Cummings

in Crazy people 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 that Don often 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 sex with Candace claiming he thinks she likes it when she objects to it.

Later in season 4, Draper introduces Lane Price (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

Alison

Played by Alexa Alemanni

Allison (Alexa Alemanni) became Don’s secretary after Peggy became a copywriterAnd, in turn, she became another one of Don Draper’s mistresses. Don brings you along as he browses Sterling Copper to co-found Sterling Copper Draper Price. Alison succumbs to her attraction to Don and sleeps with him after the office Christmas party.

She was then heartbroken when Draper pretended it never happened and gave her money as a Christmas bonus. Alison is one of Don’s affairs that makes him look really terrible. She is shown to be a very efficient and successful secretary for him, which makes her dismissal from the office even more evident.

In the aftermath of her leaving, Don is shown to begin writing an apology letter to her that shows he is aware of his terrible behavior, but eventually discards it. Joan Harris (Christina Hendricks) replaces Alison with the older Ida Blankenship (Rande Heller), a sign that Don can’t be trusted not to 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 (Pyton List) With whom Don is determined. 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 that 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 makes a couple of key people in Don’s life jealous: Ted Chao (Kevin Rahm) and his wife run into Don and Bethany at Benihana, and later, Betty is furious when she finds herself at the same restaurant as Don and Bethany.

finally, Don writes about Bethany in his journal, Lament that he knows who she is up to this point, and it’s not the person he wanted her to be.

9

Alice & Doris

Played by Amy Motta & Becky Wahlstrom

The combination of two very short affairs with two different women are used to show the further spiral nature of Don’s behavior. When Don wins a Clio Award in Crazy people Season 4 “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 celebrating his Clio.

But when he wakes up in the morning, He is next to a waitress named Doris (Becky Wallstrom), whom he does not 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 the two women, the show highlights the destructive path Dawn is on. Although 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 firm that works with Sterling Cooper Draper Pryce in Crazy people Season 4.

Dr. Faye Miller (Cara Buono) is one of Don Draper’s smartest mistresses. Miller is a consultant for a consumer research firm that works with Sterling Cooper Draper Pryce in Crazy people Season 4. They don’t get off to a great start, as Dawn is unwelcoming and unconvinced of the importance of Faye’s work.

However, as they begin to develop more of a professional relationship, Don becomes interested in moving it into unprofessional territory. Faye is initially skeptical of 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 deserts being discovered by the US.

Don ends the relationship after he proposes to Megan, and a heartbroken Faye tells him that she hopes his fiance knows that Don “Only likes the beginning of things.”

7

Andrea Rhodes

Played by Mädchen Amick

While Don Draper has a lot of dark sides to him, he seems to avoid confronting his problematic relationship with women. He has an affair with no regrets, but there are several moments that suggest there is an underlying guilt that he refuses to address openly. One example of this comes in the season 5 episode of Mad Men, “Mystery Day.”

The newlyweds Don and Megan Run into Andrea Rhodes (Mädchen Amick) in the elevator Crazy people 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 tries to sleep with him.

Then strangles her to death and hides her body under the bed. It was only a dream, but Don “killing” Andrea was one of Crazy peoples most funny and disturbing moments. It also suggests that these affairs and his relationships with women are secrets that he wants to bury deep down never to be revealed.

6

Sylvia Rosen

Played by Linda Cardinelli

Among the many mistresses, there were several Don Draper could have loved if he was able, and there is a feeling that Sylvia was one of them. Don surprisingly did not have any known affairs during the early part of his marriage to Megan Crazy people Season 5, but in 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).

Dawn and Sylvia conduct their affair under Megan and Arthur’s nose, however, she is also a friend of Megan and breaks it off when the guilt is too much. This leads to Don becoming obsessive about how he can 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

screamNeve Campbell is one of the biggest names to guest star Crazy peopleAppeared in only one episode with a very interesting storyline with Dawn. Technically, Lee Cabot (Campbell) is not one of Don Draper’s mistresses and Don did not have an affair with her. The two meet on a red-eye flight from LA to New York in Crazy peopleSeason 7 premiere.

Draper is clearly attracted to Lee, a wealthy widow, and they share an intimate plane ride home, but Dawn turns down her invitation to “share a taxi” With Lee when they land in New York. It 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 real issues. Crazy people Love to examine the reality of fleeting relationships with people coming in and out of each other’s lives and Lee makes for a more memorable addition to such a story.

4

Amy

Played by Jenny Wade

Part of what makes Don such an unlikeable character is because of the deceitfulness of all his affairs. It’s not just how he treats the women he sleeps with as disposable, but how he disrespects his wife at the same time. Throughout much of the series, Betty and Megan are unaware of his affairs. However, this is one instance where 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, it is sad as if Megan is trying to make Don feel as if 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 Kirsten Ford

Tricia (Kirstin Ford) is not only one of the many Don Draper mistresses, but still Another flight attendant Don became acquainted with when he flew to LA on weekends to visit Megan in Crazy people season 7. However, she is an example of how Dawn is willing to pursue flings a little more 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 answering service while she is on a layover and asks to meet. They go to his apartment, where she accidentally ends up crying on his white carpet. In a sign of his immense wealth and that he does not care for the apartment that his wife furnishes, he decides to have sex with Tricia on the couch.

2

Diana Bauer

Played by Elizabeth Reaser

While out on the town with some female companions and just before getting Tricia’s call for their impromptu hookup, Don becomes fixated with a waitress at a diner whom Draper thinks he met before. The waitress’s name is Diana Bauer (Elizabeth Reaser) and she turns out to be a desperately sad woman who leaves her son in the Midwest. When she disappears, Don drives to Wisconsin to try to find her.

The fact that she was a woman who was ashamed of her past and trying to run away from it clearly resonated with Don, because he had been doing a similar thing most of his life.

like Crazy peoplethe end drew near, Diana was a strange affair for Don to fixate on, But she provided some impetus for Draper to leave New York at the end of the series. The fact that she was a woman who was ashamed of her past and trying to run away from it clearly resonated with Don, because he had been doing a similar thing most of his life.

1

IV

Played by Fiona Gubelman

Eve (Fiona Gubelman) was the last of Don Draper’s mistresses Crazy peoples series finale. When 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 gets caught, she doesn’t apologize. Don gives her the money anyway, insisting that he would have it if she asked, and she thanks him for it.

No doubt, there are still issues here Crazy people ended, especially if he returned to New York to pursue his advertising career. However, this is an interesting final one on the road to Don’s self-discovery in the final moments of the series. For Eve, he was a rich market to get some money, when he was on the way to separate himself from such an identity. In the end, she helped reinforce that changing wasn’t so easy for Don.

Which of his mistresses should Don have ended up with

Don Draper was no slouch when it came to extramarital affairs. Affairs never solved his problems, though, and most of the women ended up better for it when Don didn’t rule their lives. Nevertheless, Sally’s teacher, Susan Farrell, could be the right choice for the ad executive, because she was one of the more innocent and seemed to have legitimate feelings for Don. Not only that, but these were the qualities that Don liked, suggesting he might have seen how right for him she was.

Rachel Menken was another mistress who may have had a real chance with him. Although their affair was short-lived, the two had an obvious chemistry, and Don was honest with her about his true identity. Don even dreams of her just before knowing of her death. however, None of these women were really a long-term optionAnd Don Draper in Crazy people Often cut the consequences of his actions.

How did Don Draper’s affairs affect his life

Assessing how Don Draper’s mistress and perpetual infidelity impacted his life is one of the most interesting aspects of the Crazy people Character. There are two sides of the coin, because on the one hand they caused him significant trouble, but on the other hand they were not the return of his goals and ambitions that they could have been.

Don Draper’s affairs clearly had a significant impact on his mental state. This was all too clear 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 that Don could stop even if he wanted to, and there are many 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. It started from the moment he stopped being Dick Whitman and stole the Don Draper identity. This must be constantly on guard, so that the past does not return to him, so that he does not lack any anxiety. Every affair Don Draper has compounds this – and the impact is often worse due to the fact that he has several mistresses. Crazy people Risking his peers discovering that he is, in fact, Dick Whitman.

However, it can also be said that Don Draper’s affairs did not impact his life anywhere near as much as they should. Yes, his infidelity eventually led to Betty divorcing him, and some 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 up on Crazy people 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 broke his life. Considering how many he’s had, that’s a pretty mind-blowing realization – even more so when you factor in how many of​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​a women were with women linked to his professional life. finally, Crazy people Did not shy away from the fact that Don Draper’s attitude to sex has created problems, but it is also unrealistic in many ways when it came to the lack of real consequences.