Don Draper (Jon Hamm) had 19 mistresses throughout Mad Men‘s seven seasons, not counting his three wives. Created by Matthew Weiner, 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 (later, Sterling Cooper Draper Pryce) also carried on extra-marital affairs, Donald F. Draper by far had the most. Draper is really Richard “Dick” Whitman, and he stole the identity of Lt. Don Draper (Troy Ruptash), who was killed in the Korean War. Posing as the injured-in-action Lt. Draper so he could escape the war, the “new” Don’s ruse was discovered by Lt. Draper’s widow, Anna (Melina Page Hamilton). However, Anna and Don became friends, and they maintained their “marriage” until he met Betty Hofstadt (January Jones). From there, Don Draper/Dick Whitman went on to have an unrivaled infidelity streak.
Don divorced Anna and married Betty with her blessing. 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 though, it turned out. 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 fans saw in the episodes of Mad Men. But regardless of what his grand total actually might be, 19 women in seven seasons of Mad Men (outside his wives) is the number of affairs the ad executive is seen to have on screen. Here’s the backstory on all 19 of Don Draper’s mistresses.
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Midge Daniels
Midge (Rosemarie DeWitt) is the first of Don Draper’s mistresses fans meet in Mad Men‘s pilot. Midge is a bohemian artist who is a sharp contrast to the slick Madison Avenue ad man. Midge is also a swerve as audiences are initially led to believe Midge 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. Don’s fling with Midge ends in season 1, but she reappears in Mad Men season 4. Sadly, Midge has become addicted to heroin and Jon Hamm’s Draper cuts her a check before vanishing from her life.
Rachel Menken
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. In Mad Men season 2, Don ran into Rachel, who is now married, and in season 3, Don is sad to learn that Rachel died of leukemia.
Joy
Joy (Laura Ramsey) was 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. The free-spirited Joy may have been the youngest of Don’s flings in Mad Men.
Bobbie Barrett
Bobbie Barrett (Melinda McGraw) was the wife and manager of comedian Jimmy Barrett (Patrick Fishler). Don meets Bobbie after Jimmy upsets the owner of his sponsor, Utz Potato Chips, and their affair included getting in a car accident that required Peggy (Elisabeth Moss) to help out and let Bobbie stay with her. Don ended their Mad Men season 2 relationship when he learned Bobbie had been gossiping about his prowess in the bedroom.
Shelly
Shelly (Sunny Mabrey) was a stewardess Don had a one-night stand with when Don traveled to Baltimore with Sal Romano (Bryan Blatt) in Mad Men season 3. Shelly invited Don and Sal to dinner with her flight attendant friends, but she was gone after a fire alarm evacuated the hotel. But 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.
Suzanne Farrell
Suzanne Farrell (Abigail Spencer) was Sally’s teacher who was Don’s last mistress before Betty ended their marriage. Despite her hesitation, Suzanne began an affair with Don, but it abruptly ended right when they were planning to leave on a vacation together at the end of Mad Men season 3. Betty had discovered Don’s hidden records that he was really Dick Whitman and confronted him, which immediately put an end to Draper’s tryst with Miss Farrell.
Candace
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 prostitute Don frequently hired, and 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.
Allison
Allison (Alexa Alemanni) became Don’s secretary after Peggy became a copywriter, and he brought her along when he left Sterling Cooper to co-found Sterling Cooper Draper Pryce. Unfortunately, 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 quit SCDP, and Joan Harris (Christina Hendricks) replaced her with the elderly Ida Blankenship (Randee Heller).
Bethany Van Nuys
Bethany Van Nuys (Anna Camp) is a friend of Roger Sterling’s young bride Jane (Peyton List) who Don is set up with. Despite her youth and charms, Don doesn’t have much chemistry with Bethany, and he eventually ends things after a few dates. However, Bethany on his arm does make a couple of key people in Don’s life jealous: Ted Chaough (Kevin Rahm) and his wife ran into Don and Bethany at Benihana’s, and later, Betty is furious when she finds herself at the same restaurant as Don and Bethany.
Alice and Doris
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, but he later wakes up next to a waitress named Doris (Becky Wahlstrom), whom he doesn’t recognize. Worse, Doris calls him “Dick,” which means he drunkenly called himself by his secret birth name and not his carefully maintained Don Draper identity during his blackout tryst with the waitress.
Dr. Faye Miller
Dr. Faye Miller (Cara Buono) is a consultant for a consumer research company working with Sterling Cooper Draper Pryce in Mad Men season 4. 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 the heartbroken Faye tells him that she hopes his fiancée knows that Don “only likes the beginnings of things.”
Andrea Rhodes
The newlywed Don and Megan ran into Andrea Rhodes (Mädchen Amick from Twin Peaks) in the elevator in Mad Men season 5. From Andrea’s relentless flirting with Don, it was clear they were lovers in the past, although when it happened wasn’t disclosed. When Don is feverishly ill, Andrea entered his apartment and attempted 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.
Sylvia Rosen
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, no less. Sylvia Rosen (Linda Cardinelli, most known these days as Hawkeye’s wife Laura Barton in the MCU) 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 until Sally accidentally walks in on her father having sex with his neighbor, which immediately put an end to it.
Lee Cabot
Technically, Don didn’t have an affair with Lee Cabot (Neve Campbell), who he meets 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.
Amy
Amy (Jenny Wade, whose pre-Mad Men filmography includes as an extra on American Horror Story) 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.
Tricia
Tricia (Kirstin Ford) is a stewardess Don became acquainted with when he flew to LA on weekends to visit Megan in Mad Men season 7. Tricia calls Don’s answering service and left a message that she was in town. When Don calls her over to his apartment, Tricia spills red wine on his white carpet.
Diana Bauer
While out on the town with some female companions, Don becomes fixated with a waitress at a diner who Draper thinks he met before. The waitress’ name is Diana Bauer (Elizabeth Reaser from The Haunting of Hill House) 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. As Mad Men drew to a close, 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.
Eve
Eve (Fiona Gubelman) was Don Draper’s final mistress 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 beds. She tries to steal his wallet, but Don catches her and gives her money anyway. No doubt, Don continued having affairs after Mad Men ended, especially if he returned to New York to resume his advertising career.
Which of His Mistresses Should Don Have Ended Up With
Don Draper on Mad Men wasn’t lacking when it came to extramarital affairs. So, out of all 19 women, who do people believe Draper should’ve ended up with? Starting out, it should at least be said that affairs are never the answer, and most of these women ended up better for it when Don didn’t reenter their lives. Truthfully, no one deserves to be cheated on, especially not as often as Draper did to his three wives. Some believe that Suzanne (Sally’s teacher) was the right choice for the ad executive, as she was one of the more innocent of the bunch and seemed to harbor legitimate feelings for Don. Rachel Menken was another popular choice for Don to end up with by the end of Mad Men. Despite their affair being short-lived, the two had obvious chemistry, and Don was honest with her about his true identity. In addition, she fell in love believing that Don was a single man, whereas other mistresses knew that he was married. Megan and Faye were also popular choices. Regardless, cheating is never right, and Don Draper in Mad Men often reaped the consequences of his actions.