Don Draper's Many Female Companions: Exploring His Relationships

Don Draper's womanising is a central theme of Mad Men, with the character having 19 mistresses throughout the seven seasons of the show, not counting his three wives. Draper's infidelity is well-known within his workplace, and it is clear that he has many more affairs offscreen. Draper's first wife, Betty, divorces him after discovering his infidelity, and he goes on to marry his secretary, Megan Calvet, between seasons 4 and 5. However, he is unable to stay faithful to Megan either, and their marriage ends after she discovers his hidden records.

Don Draper's three wives

Betty Hofstadt (January Jones)

Betty, Don's first wife, is a former model and acts as his charming and loving spouse at important client dinners. However, at home, she is cold, sometimes cruel, and deeply unhappy in her role as a housewife. She is also unaware of Don's dark past until she discovers it in season 3, leading to their separation. Despite their divorce, they remain civil and continue to share custody of their three children.

Megan Calvet (Jessica Pare)

Megan starts off as Don's secretary but becomes his second wife after he impulsively proposes to her while she takes care of his kids. Their relationship is strained by Don's infidelity, and Megan eventually ends the marriage.

Anna Draper (Melinda Page Hamilton)

Anna Draper is the true wife of Lieutenant Donald Draper. After her husband's death in the Korean War, she forms a deep platonic bond with Dick Whitman (Don's real name), who assumes her late husband's identity. Don often visits Anna in California and continues to support her financially even after he divorces her to marry Betty.

Don Draper's mistresses

Don Draper had a lot of mistresses throughout the seven seasons of Mad Men. While the other ad men of Sterling Cooper also carried on extra-marital affairs, Don Draper had the most by far.

Draper's first wife, Betty Hofstadt, was unaware of Don's infidelities until she stumbled across a secret drawer in season 3 and later divorced him. Despite this, Don and Betty continued to sleep together, even after he remarried.

• Midge Daniels, a bohemian artist and Don's first mistress, introduced in the pilot episode.
• Rachel Menken, a Sterling Cooper client who owned a department store.
• Joy, a wealthy nomad Don meets in Los Angeles.
• Bobbie Barrett, the wife and manager of a comedian.
• Shelly, a stewardess Don meets on a business trip to Baltimore.
• Suzanne Farrell, Sally's teacher.
• Candace, a sex worker.
• Allison, Don's secretary.
• Bethany Van Nuys, an aspiring actress and friend of Roger Sterling's wife.
• Alice and Doris, two women Don meets at a bar.
• Dr. Faye Miller, a consultant for a consumer research company.
• Andrea Rhodes, a woman Don meets after marrying his second wife, Megan Calvet.
• Sylvia Rosen, the wife of Don's friend and neighbour, Arthur Rosen.
• Amy, a friend of Megan's in California.
• Tricia, a stewardess Don meets on flights to LA.
• Diana Bauer, a waitress.

Don Draper's most memorable affairs

Don Draper's womanising ways are well-documented in the series Mad Men. Over the course of the show's seven seasons, Draper has 19 mistresses, in addition to his three wives. Here is a look at some of his most memorable affairs.

Midge Daniels (played by Rosemarie DeWitt): Midge is Don's mistress in the show's first season. She is a bohemian artist, which serves as a sharp contrast to Draper's corporate world. Midge is initially presented as Don's significant other, but it is later revealed that he is married to Betty and has two children. Midge reappears in season four, married to someone else and addicted to heroin. Don cuts her a cheque and vanishes from her life.

Rachel Menken (played by Maggie Siff): Rachel is a client of Sterling Cooper, the ad agency where Don works. She owns a department store. Don proposes that they run away together to Los Angeles, but she sees through his plan to simply run away from his life and problems. In season two, Don runs into Rachel, who is now married, and in season three, he learns that she has died of leukaemia.

Bobbie Barrett (played by Melinda McGraw): Bobbie is the wife and manager of a comedian, Jimmy Barrett. She meets Don after her husband insults the wife of a client. Their relationship is unhealthy and includes a drunken car crash while driving to Bobbie's beach house. Don ends the affair when he learns that Bobbie has been gossiping about his prowess in the bedroom.

Suzanne Farrell (played by Abigail Spencer): Suzanne is Sally's teacher and has an affair with Don despite her initial hesitation. Their relationship ends when Betty discovers Don's hidden records and learns that he is not who he says he is.

Sylvia Rosen (played by Linda Cardinelli): Sylvia is the wife of Don's friend, Dr Arthur Rosen. They have an affair under their spouses' noses, but Sylvia ends it when the guilt becomes too much. Don becomes obsessive, and their affair ends when Sally walks in on them.

Don Draper's most meaningful relationships

Don Draper's character in Mad Men is known for his womanising ways, with 19 mistresses throughout the seven seasons of the show, not counting his three wives. Here is an overview of some of Don Draper's most meaningful relationships:

Betty Draper (January Jones)

Betty is Don's first wife and the mother of his two children. She is a former model who acts as a charming and loving spouse in public, but at home, she is cold, sometimes cruel, and deeply unhappy as a housewife. Despite having two kids with Betty, Don cheated on her numerous times. In season 3, Betty discovers Don's dark past and true identity as Dick Whitman, leading to their divorce. Despite this, they remain civil, and there is still chemistry between them, as evidenced by a sexual encounter in season 6.

Midge Daniels (Rosemarie DeWitt)

Midge is Don's mistress in the first season of Mad Men. She is a bohemian artist and illustrator who offers Don an escape from his corporate world, as she and her friends see it as the enemy. Midge is a stark contrast to Don's wife, Betty, and their relationship ends when Midge falls in love with a male friend. Midge reappears in season 4, married to someone else and struggling with heroin addiction.

Rachel Menken (Maggie Siff)

Rachel is a Sterling Cooper client who owns a department store. She is smart, classy, and bold, and Don becomes enamoured with her. Their relationship is meaningful as Don confesses details of his life as Dick Whitman to Rachel. He even proposes that they run away together to Los Angeles, but she sees through his attempt to run away from his problems. In season 3, Don is saddened to learn that Rachel has died of leukaemia.

Anna Draper (Melinda Page Hamilton)

Anna Draper is the true wife of Lieutenant Donald Draper, whose identity Don Draper assumed. Anna and Don form a deep platonic bond, and Don often visits her in California, continuing to support her financially even after he divorces her to marry Betty. When Anna dies of terminal cancer in season 4, Don reveals to Peggy that she was "the only person in the world who really knew me."

Megan Calvet Draper (Jessica Paré)

Megan starts as Don's secretary and becomes his second wife after he impulsively proposes to her while she takes care of his children. Their relationship is meaningful as Megan is the only one of Don's wives who is aware of his dark past as Dick Whitman from the beginning of their relationship. However, Don's infidelity continues, as he has an affair with his neighbour, Sylvia Rosen, while married to Megan.

Sylvia Rosen (Linda Cardellini)

Sylvia is the wife of Don's friend, Dr Arthur Rosen, and a friend of Megan's, making her affair with Don particularly meaningful and impactful. Don and Sylvia carry on their affair under their spouses' noses, but Sylvia eventually tries to end it due to her guilt. Don becomes obsessive, loitering outside her home, and they resume their relationship until Sally, Don's daughter, catches them in the act, bringing it to an end.

Don Draper's relationships are marked by infidelity, secrecy, and complex dynamics, providing a fascinating exploration of his character and the societal norms of the time.

Don Draper's relationships with his wives' friends

Don Draper's relationships with his wives and friends are complex and often fraught with infidelity. Over the course of the series, Don has three wives: Betty Hofstadt, Megan Calvet, and an unknown third wife. Despite having two children with his first wife, Betty, Don cheats on her numerous times as his advertising career takes off. Their relationship ends when Betty, who long suspected Don's infidelities, discovers that he is not who he claims to be.

Between his first and second marriages, Don has a string of affairs with various women, including Midge, a bohemian artist; Rachel Menken, a client of Sterling Cooper; Joy, a wealthy nomad he meets in Los Angeles; and Bobbie Barrett, the wife and manager of a comedian. Don's second marriage is to his secretary, Megan Calvet. Despite his infidelity, Don and Megan's relationship seems to be more stable than his first marriage, and they remain together through the series.

One of the most notable aspects of Don's relationships is his tendency to mix his personal and professional lives, often engaging in affairs with women he works with or who are connected to his business. This includes his secretaries, Allison and Megan, as well as a client, Rachel Menken. Don's relationships with his wives and friends are also marked by his inability to be faithful, his complex past, and his tendency to be controlling and manipulative.

Don's relationships with his wives' friends are also complex. For example, he has an affair with Sylvia Rosen, the wife of his friend Dr. Arthur Rosen, and Megan's friend, Amy. Don's relationships with his wives' friends often involve deception and a lack of trust, which further complicates his marriages.

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