Don Draper's Womanizing: A Tiring Trope?

Don Draper, the ultra-suave star of Mad Men, is a womaniser. He's been married twice, divorced once, and is always ready for a new romance. From the pilot episode, Don Draper was sleeping with multiple women. He might not always be happy about it, but he’s always got a side girl. Over the course of 92 hour-long episodes, Don Draper has been with at least 15 women.

Draper's conquests include his first wife, Betty, a former model; Midge, an artist and free-spirited pothead; Rachel, the head of a department store; Bobbie, the wife of a comedian; and many more.

Don Draper's type

Don Draper, the ultra-suave star of Mad Men, is a ladies' man. He is a mystery, even to himself, and his collection of lovers reflects that. Draper is a married man who sleeps with multiple women throughout the show's 92 hour-long episodes.

Draper is also attracted to women who are similar to his ex-wife, Betty. After his divorce, he seeks out blonde, naive, and simple-minded women who remind him of Betty. For example, Bethany, a friend of Roger Sterling's wife, is described as a "pretty but dull companion" who looks like a younger version of Betty. Another example is Suzanne, Sally's brunette teacher, who Don imagines as a "dancing, maypole vision of simple idealistic virtue."

Finally, Don Draper is attracted to women who represent a maternal figure. For example, Sally's teacher, Suzanne, embodies "squeaky-clean maternal goodness." Similarly, Candace, a prostitute Don visits, represents the mother/whore figure. Don's relationship with Candace is interesting because his own mother was a prostitute, and he feels guilty about betraying her memory.

In conclusion, Don Draper's type is complex and multifaceted. He is attracted to the fantasy of a new beginning, the familiarity of a woman like his ex-wife, and the comfort of a maternal figure. Throughout the show, Don Draper seeks to escape his past and find a new beginning, and his lovers reflect this desire.

Don Draper's fantasy versions of women

Don Draper's womanising ways are a central theme of Mad Men. Draper has three wives and 18-19 mistresses throughout the show's seven seasons.

Draper's first wife, Betty, is a former model who 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. Draper is unfaithful to her numerous times, and she eventually divorces him after learning about his infidelities and that he is really Dick Whitman.

Draper's romantic pursuits often overlap with his business life. Bobbie Barrett, the wife and manager of a comedian, is one such example. Draper admires her boldness and the fact that she is clearly in charge of her marriage. However, he ends their relationship when he learns she has been gossiping about his prowess in the bedroom. Another of Draper's conquests is Rachel Menken, a Sterling Cooper client who owned a department store. She is smart, classy, and bold, and Don becomes completely enamoured with her. She initially resists his advances due to his marital status, but eventually succumbs. Don proposes that they run away together to Los Angeles, but she can see through him, realising that he simply wants to run away from his life.

Draper's relationships are often transactional and hypocritical. For example, he has a one-night stand with a stewardess, Shelly, while on a business trip to Baltimore, but gets angry when his colleague Sal does the same thing with another man. He also frequents sex workers, including Candace, whom he hires for a rough session on Thanksgiving Day.

Draper's secretaries are not off-limits either. Allison, who becomes Don's secretary after Peggy, sleeps with him after the office Christmas party. The next day, Draper pretends like it never happened and gives her cash as a Christmas bonus. Draper's current wife, Megan, starts off as his secretary as well. He impulsively proposes to her while she is taking care of his kids and they eventually marry. However, he is unfaithful to her as well.

Draper's relationships are often fantasy versions of women, where he can escape from his corporate life and his role as a husband and father. He is a mystery, even to himself, and his collection of lovers paints a strange portrait of the man.

Don Draper's relationship with his wife

After his divorce from Betty, Don marries his secretary, Megan Calvet, and they move to a stylish Upper East Side apartment on Park Avenue. However, their relationship is not without its challenges. In season 5, Don has vivid fever dreams about sleeping with another woman, Andrea, whom he and Megan meet in an elevator. Later in the series, Don has an affair with their neighbour, Sylvia Rosen, which ends when their daughter Sally catches them in the act.

Throughout the series, Don's relationships with his wives are impacted by his numerous affairs, his erratic behaviour, and his struggles with identity and social alienation. Despite this, Don and Betty maintain a civil relationship after their divorce, and he offers to come and live with Megan in Los Angeles, although she refuses. The ultimate fate of Don and Megan's relationship is left ambiguous at the end of the series.

Don Draper's relationship with his co-workers

Firstly, it is important to note that Don Draper is a partner at the advertising firm, Sterling Cooper, and later, Sterling Cooper Draper Pryce, and thus holds a position of power over his secretaries and other employees. This dynamic is often reflected in his relationships with his female co-workers, which are frequently sexualized and involve a certain degree of manipulation.

One of Don's most significant relationships with a co-worker is with his secretary, Allison. Their relationship begins when Allison, smitten with Don, brings him his keys after the office Christmas party. They have a one-night stand, after which Don refuses to acknowledge their encounter, leaving Allison heartbroken. She resigns from her position and asks Don for a recommendation, to which he coldly replies that she should write one herself and he will sign it. This incident highlights Don's callousness and the power imbalance between them.

Another notable relationship is with Peggy, Don's protégée. Their relationship is fraught with sexual tension, and there is a constant "will-they-won't-they" dynamic hanging over them. However, they have thus far managed to keep their relationship platonic and professional.

Don also has a complex relationship with Joan, a fellow partner at the firm. They share a deep emotional connection and have supported each other through various difficulties. There is a suggestion of sexual tension between them, and they once share a flirtatious, emotional night at a bar. However, Don ultimately chooses to respect their relationship and leaves without acting on his desires, demonstrating a rare moment of restraint.

In addition to these relationships, Don has numerous affairs with other female co-workers, such as Suzanne, Sally's teacher, and Bethany, the friend of Roger Sterling's wife. These relationships often involve manipulation and a power imbalance, reflecting Don's troubled nature and his struggle to find genuine connection.

Don Draper's relationship with prostitutes

Don Draper, the protagonist of Mad Men, is revealed to be the assumed identity of Richard "Dick" Whitman, who was born to a teenage prostitute, Evangeline, and an abusive, alcoholic farmer, Archibald "Archie" Whitman. Archie was married to Abigail, and Evangeline gave birth to Don. Evangeline died in labour, and the midwife brought the baby to be raised by Abigail and Archie.

In the Mad Men episode "The Crash", Don, under the influence of drugs, relives the moment he lost his virginity to a prostitute named Aimee when he was a teenager. Aimee nurses Don back to health after he falls ill with a nasty chest cold. However, Aimee's maternal kindness turns predatory when she gets into bed with Don, and despite his protests, she rapes him.

Don's complicated feelings towards women and struggles with fidelity are linked to his past. Viewers learn that Don, as a child, was left under the care of Aimee, a prostitute, after he fell ill. Don's first sexual encounter with Aimee influences his perception of sex and his treatment of women throughout the series.

In addition to Aimee, Don regularly sees a prostitute named Candace. In one episode, Don and his colleague Lane Pryce visit a comedy club on New Year's Eve, where they meet Candace and her friend Janine. Back at Don's place, Don and Candace stay on the couch, while Lane and Janine go to the bedroom.

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