Don Draper's Many Female Bedfellows: Exploring His Sexual Conquests

Don Draper, the ultra-suave star of AMC's Mad Men, is known for his romantic encounters with numerous women throughout the show's seven seasons. Draper's relationships with women, including both his wives and mistresses, have been a central focus of the series, with his infidelity streak unrivalled by the other ad men of Sterling Cooper. While the exact number of women Don sleeps with is unclear, estimates range from 15 to 19, in addition to his three wives. From secretaries to stewardesses, Don's conquests reveal a lot about his character and the time period in which the show is set.

Don Draper's three wives

Don Draper's romantic life is a complex web of relationships, with a long list of mistresses and multiple marriages. Despite his many affairs, there are only three women who earned the title of Mrs. Draper: Betty Hofstadt, Megan Calvet Draper, and Anna Draper.

Anna Draper

Anna Draper was the wife of Lieutenant Donald Draper, whose identity Don Draper (born Dick Whitman) assumed after his death in the Korean War. While their relationship was never romantic, it was one of the most important in Don's life. Don often visited Anna in California and continued to pay her expenses even after he divorced her to marry his first wife, Betty. When Don learns of Anna's death from terminal cancer, he reveals to his colleague Peggy that she was "the only person in the world who really knew me."

Betty Hofstadt

Played by January Jones, Betty is Don's first wife and the mother of his two children. A former model, she acts as his charming and loving spouse at important client dinners, but at home, she is cold, sometimes cruel, and deeply unhappy in her role as the typical American housewife. Unaware of Don's dark past and infidelity, Betty finally extricates herself from their relationship after discovering his secret drawer in season 3 and learning his true identity. She divorces Don and marries Henry Francis, a politician, but despite their new spouses, there is still chemistry between Don and Betty, and they sleep together while visiting their son at camp in season 6.

Megan Calvet Draper

Megan starts off as Don's secretary but quickly becomes his second wife after Don impulsively proposes to her while she takes care of his children on a trip to California. Despite his attempts to keep his private life and work life separate, Don is unable to stay faithful to Megan, and his affairs become well-known within his professional circle. Their marriage ends when Megan refuses Don's offer to come live with her in Los Angeles, and he becomes obsessed with getting back together with one of his previous mistresses, Sylvia Rosen.

In addition to his three wives, Don Draper had numerous affairs throughout the series, with 18 to 19 mistresses across seven seasons, not including his wives.

Don Draper's 19 mistresses

Don Draper, the ultra-suave star of AMC's Mad Men, has been married twice, divorced once, and has had numerous affairs. He has had 19 mistresses throughout the seven seasons of the show, not counting his three wives.

• Midge Daniels: A bohemian artist and the first of Don Draper's mistresses introduced in the pilot episode of Mad Men. Midge is a sharp contrast to the slick Madison Avenue adman, offering him an escape from the corporate world. She reappears in Season 4, married to someone else and addicted to heroin.
• Rachel Menken: A Sterling Cooper client who owned a department store. Don and Rachel had a mutual attraction, and he proposed that they run away together to Los Angeles. However, she realised he was running away from his life and using her as an excuse.
• Joy: A wealthy nomad Don meets when he travels to Los Angeles in Season 2. Joy aggressively pursues Don, and they spend a few days together before he leaves to visit Anna Draper and return to New York.
• Bobbie Barrett: The wife and manager of comedian Jimmy Barrett. Don meets Bobbie after Jimmy upsets the owner of his sponsor, Utz Potato Chips. Their affair includes a drunken car crash while driving to Bobbie's beach house, and Don ends it when he learns that she has been gossiping about him.
• Shelly: A TWA stewardess Don meets on a flight to Baltimore in Season 3. They have a one-night stand in a hotel room, which is interrupted by a fire alarm. Shelly disappears, and Don gives her pin-on wings to his daughter Sally.
• Suzanne Farrell: Sally's teacher who has an affair with Don. She is initially hesitant but eventually gives in to his charms. Their relationship ends when Betty confronts Don about his true identity.
• Candace: A sex worker/call girl/prostitute Don frequently hires and has a rough relationship with. In one scene, she slaps Don in the face during sex, and he asks for more.
• Alice: A woman Don meets at a bar and sleeps with after winning the Clio for his Glo-Coat commercial.
• Doris: A disheveled diner waitress whom Don wakes up next to after a drunken night. He introduces himself to her as Dick, his real name.
• Dr. Faye Miller: A consultant for a consumer research company working with Sterling Cooper Draper Pryce. Don and Faye have a professional relationship, but he eventually pursues a romantic one. She is one of the few women to whom Don reveals his past.
• Andrea Rhodes: One of Don's previously unseen mistresses, who flirts with him relentlessly when he meets her with his new wife, Megan. In a fever dream, Don chokes her to death and hides her body under the bed.
• Sylvia Rosen: The wife of Don's friend, Dr Arthur Rosen, and a neighbour and friend of Megan. Don and Sylvia have an affair, which ends when Sally catches them in the act.
• Lee Cabot: A wealthy widow whom Don meets on a flight from LA to New York. They share an intimate plane ride, but Don turns down her invitation to "share a cab" when they land.
• Amy: One of Megan's friends in California, who has a threesome with Don and Megan.
• Tricia/Trisha: A stewardess Don meets on his flights to LA to visit Megan. They have a casual fling, and she accidentally spills wine on his rug during one of their encounters.
• Diana Bauer: A waitress Don becomes fixated on after seeing her at a diner. She is a desperately sad woman who abandoned her son, and Don drives to Wisconsin to try to find her.
• Aimee: A prostitute who took Don's virginity when he was a child.
• Blonde Bimbo: A prostitute Don sleeps with in Utah.
• Blonde Bimbo: Another prostitute Don invites to his apartment.

Don Draper's prostitute encounters

Don Draper's first sexual encounter was with a prostitute named Aimée, who nursed him back to health when he was a child. This encounter is considered rape by some viewers, as it was non-consensual, but Don himself does not seem to view it as such. Instead, he associates the experience with being cared for and given what he needed, reflecting his complicated perspective on sex and his relationships with women.

As an adult, Don Draper frequently hires prostitutes and has several encounters with them throughout the series. In Season 4, he hires a prostitute named Candace for a rough session on Thanksgiving Day, indicating a previous relationship. He also introduces her to his colleague Lane Pryce to cheer him up when his marriage is struggling. In Season 7, Don sleeps with a blonde prostitute in his ex-wife's apartment and another in Utah, reflecting his self-destructive behaviour and inability to break free from his past.

Don's relationships with prostitutes are often transactional and reflect his spiral into darkness. His encounters with Candace and other prostitutes highlight his problematic relationship with women and his tendency to treat them as disposable. Don's behaviour towards prostitutes also demonstrates his hypocrisy, as he engages in extramarital affairs while getting angry at others for doing the same.

Don Draper's affairs with his employees

One notable exception to Don's tendency to avoid mixing his personal and professional lives is his affair with Rachel Menken, a Sterling Cooper client who owns a department store. Don proposes that they run away together to Los Angeles, but she sees through his attempt to escape his life and rejects him.

Another of Don's affairs with an employee is with his secretary, Allison. After sleeping with Don, Allison is heartbroken when he pretends like it never happened and gives her cash as a Christmas bonus. She eventually resigns from her position.

Don also has a brief affair with Midge Daniels, a beatnik illustrator and painter who he often spends lazy afternoons with. Their relationship ends when Midge refuses Don's proposal to run away to Paris and he discovers she is in love with someone else.

Don's third wife, Megan Calvet, is also his employee. He marries his secretary between seasons 4 and 5, but is unable to stay faithful to her.

Don Draper's affairs with his clients

Don Draper's womanising behaviour is well-known, with 19 mistresses throughout Mad Men's seven seasons, not counting his three wives. While the other ad men of Sterling Cooper also carried on extra-marital affairs, Don Draper had the most by far.

Rachel Menken

Rachel Menken (played by Maggie Siff) was a Sterling Cooper client who owned a department store. Don was completely enamoured with her and, despite her initial resistance due to his marital status, she eventually gave in to his advances. Don even proposed that they run away together to Los Angeles, but she saw through his desire to escape his life and rejected him. In Season 2, Don runs into Rachel, who is now married, and in Season 3, he learns that she has died of leukaemia.

Bobbie Barrett

Bobbie Barrett (played by Melinda McGraw) was the wife and manager of comedian Jimmy Barrett. Don met Bobbie when Jimmy upset the owner of his sponsor, Utz Potato Chips, and she tried to blackmail Don. Despite his initial resistance, they began an affair, which included a drunken car crash while driving to Bobbie's beach house. Don ended the relationship when he learned that Bobbie had been gossiping about his prowess in the bedroom.

Shelly

Shelly (played by Sunny Mabrey) was a TWA stewardess Don met on a business trip to Baltimore. Despite being engaged, they had a one-night stand in a hotel room, which was interrupted by a fire alarm. Shelly disappeared after the incident, and Don gave her pin-on wings to his daughter Sally as a memento.

Suzanne Farrell

Suzanne Farrell (played by Abigail Spencer) was Sally's teacher. She was initially hesitant about an affair with Don, but he eventually won her over. Their plans to go on vacation were dashed when Don's family returned home early, and Betty discovered Don's hidden records revealing his true identity. Don ended the affair after this confrontation with Betty.

Faye Miller

Faye Miller (played by Cara Buono) was a consultant for a consumer research company working with Sterling Cooper Draper Pryce. She and Don initially got off to a rocky start, but they eventually developed a romantic relationship. Don ended the relationship after he proposed to Megan, and Faye told him that she hoped his fiancée knew that he "only likes the beginnings of things."

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