The 19 Women Who Captivated Don Draper: A Comprehensive Guide

Article Overview

Don Draper had a total of 19 mistresses throughout the seven seasons of Mad Men, showcasing his inability to stay faithful to his partners.

Midge, Rachel, and Suzanne emerged as standout potential long-term partners for Don, thanks to their strong connection with him and their sincere emotions towards him.

Despite his numerous extramarital affairs, Don frequently faced the repercussions of his choices, as his unfaithfulness became common knowledge within Sterling Cooper and ultimately resulted in the demise of certain relationships.

Throughout the seven seasons of Mad Men, Don Draper (played by Jon Hamm) had a total of 19 mistresses, excluding his three wives. Keeping up with all of Don Draper's mistresses proves to be quite challenging. Mad Men, a prestigious series on AMC, follows the lives and careers of advertising executives on Madison Avenue during the 1960s. While other colleagues at Sterling Cooper also engaged in extramarital affairs, Donald F. Draper surpassed them all. Despite being married to Betty Hofstadt (played by January Jones), Don embarked on an unmatched streak of infidelity. Despite having two children with Betty, Don betrayed her multiple times as his advertising career flourished. In the third season, Betty, who had long suspected Don's unfaithfulness, discovered that he was actually Dick Whitman. This led to their divorce, after which Don married his secretary, Megan Calvet (played by Jessica Pare), between the fourth and fifth seasons. However, Don's inability to remain faithful persisted, and despite his best efforts to separate his personal and professional lives, his affairs became widely known within Sterling Cooper. It is evident that Don had numerous additional affairs not shown onscreen. Although the exact number is unknown, in the seven seasons of Mad Men, Don Draper was involved with a total of 19 mistresses.

Midge Daniels

Midge (Rosemarie DeWitt) was the first of Don Draper's mistresses to be introduced in the pilot episode of Mad Men. She was a bohemian artist who contrasted sharply with the polished adman of Madison Avenue. Initially, audiences were led to believe that Midge was Don's significant other, but the end of the first episode revealed that he had a wife, Betty, along with two young children in the suburbs. Don's brief affair with Midge came to an end during the first season, but she made a reappearance in the fourth season of Mad Men. Sadly, Midge had developed a heroin addiction, prompting Jon Hamm's Draper to write her a check before disappearing from her life.

Rachel Menken

Rachel Menken (Maggie Siff), a department store owner and client of Sterling Cooper, initially attracted Don's attention after he ended his affair with Midge. Their relationship, however, was short-lived. Nevertheless, Don felt compelled to reveal his true identity as Dick Whitman to Rachel. In the second season of Mad Men, Don unexpectedly encounters Rachel, who is now married. Tragically, in the third season, Don is saddened by the news of Rachel's untimely death from leukemia.

Joy

Joy (Laura Ramsey) is a wealthy nomad whom Don encounters during his trip to Los Angeles in "The Jet Set," an episode from the second season of Mad Men. Choosing to break away from Pete Campbell (Vincent Kartheiser), Don spends several days in the company of Joy and her peculiar, aristocratic circle before embarking on a visit to Anna Draper and eventually returning to New York. Among all the mistresses of Don Draper, the carefree Joy may have been the youngest.

Bobbie Barrett

The character Bobbie Barrett, played by Melinda McGraw, is introduced as the wife and manager of comedian Jimmy Barrett, portrayed by Patrick Fishler. Don encounters Bobbie after Jimmy offends the owner of their sponsor, Utz Potato Chips. Their affair becomes complicated when they become involved in a car accident, leading Peggy, played by Elisabeth Moss, to assist and host Bobbie temporarily. Don decides to end their relationship in season 2 of Mad Men after learning that Bobbie had been spreading rumors about his sexual abilities.

Shelly

Shelly (Sunny Mabrey) is one of the briefest love interests of Don Draper in Mad Men. In season 3, Don has a one-night affair with this flight attendant while he travels to Baltimore with Sal Romano (Bryan Blatt). Shelly extends an invitation to Don and Sal for a dinner with her flight attendant friends. However, their meeting is cut short as a fire alarm prompts the hotel evacuation. Despite this fleeting encounter, the true consequence of Don's trip to Baltimore is the revelation of Sal’s concealed homosexuality. This discovery ultimately leads to Romano's dismissal from Sterling Cooper.

Suzanne Farrell

Sally's teacher, Suzanne Farrell, portrayed by Abigail Spencer, becomes Don Draper's final mistress before his marriage with Betty reaches its end. Despite her initial reluctance, Suzanne embarks on an affair with Don. However, their relationship comes to an abrupt halt as they are about to embark on a vacation together at the conclusion of Mad Men season 3. Betty discovers Don's secret identity as Dick Whitman and confronts him, effectively putting an end to his affair with Miss Farrell.

Candace

Allison

In season 4 of Mad Men, Don decided to leave his home with Betty, and instead, the troubled advertising executive, played by Jon Hamm, opted for an apartment in Manhattan. One of Don's regular acquaintances is Candace (played by Erin Cummings), a sex worker whom he frequently hires. Later on in the fourth season, Draper introduces Lane Pryce (played by Jared Harris) to Candace and her friend in an attempt to lift his spirits when his marriage is on the rocks.

After Peggy became a copywriter, Allison (Alexa Alemanni) took over as Don's secretary and eventually became one of his mistresses. When Don left Sterling Cooper to start Sterling Cooper Draper Pryce, he brought Allison along with him. Despite the professional relationship, Allison couldn't resist her attraction to Don and they slept together after the office Christmas party. However, Don coldly dismissed the encounter and gave her money as a Christmas bonus, leaving Allison heartbroken. As a result, she decided to quit SCDP. Joan Harris (Christina Hendricks) then replaced Allison with the elderly Ida Blankenship (Randee Heller).

Bethany Van Nuys

Bethany Van Nuys (Anna Camp) is introduced as a companion for Roger Sterling's young wife Jane (Peyton List), as arranged by Don. While Bethany possesses youth and allure, Don does not share a strong connection with her compared to his other mistresses. Eventually, after a few dates, Don decides to end things with Bethany. However, Don's presence with Bethany does elicit jealousy from a few significant individuals in his life. For instance, Ted Chaough (Kevin Rahm) and his wife encounter Don and Bethany at Benihana's, leading to feelings of envy. Additionally, Betty becomes notably angry when she coincidentally finds herself at the same restaurant as Don and Bethany.

Alice and Doris

In "Waldorf Stories," an episode from Mad Men season 4, Don experiences a wild spree after winning a prestigious Clio Award. While celebrating, he ends up spending the night with Alice (Amy Motta), a woman he meets at a bar. However, the aftermath reveals a strange twist. Don wakes up the next morning next to Doris (Becky Wahlstrom), a waitress he doesn't recognize. To his surprise, Doris refers to him as "Dick," unintentionally exposing his secret birth name instead of his meticulously crafted identity as Don Draper from Mad Men.

Dr. Faye Miller

Dr. Faye Miller (Cara Buono) is known for her intelligence among Don Draper's many mistresses. In Mad Men season 4, she works as a consultant for a consumer research company that collaborates with Sterling Cooper Draper Pryce. Initially skeptical of Don's advances, Faye's opinion changes when he opens up about his true identity as Dick Whitman during a panic attack about his stolen identity and abandonment, which could be exposed by the U.S. government. Their relationship comes to an end when Don proposes to Megan, leaving Faye heartbroken. She bitterly remarks that she hopes Megan understands Don's tendency to only enjoy the early stages of a relationship.

Andrea Rhodes

In Mad Men season 5, the newlywed couple Don and Megan encounter Andrea Rhodes (played by Mädchen Amick from Twin Peaks) in the elevator. Andrea's persistent flirting indicates that she was one of Don Draper's undisclosed mistresses. When Don falls seriously ill, Andrea enters his apartment and tries to seduce him. In a shocking twist, Don chokes her to death and hides her body under the bed. Ultimately, the entire sequence turns out to be just a dream. However, this moment of Don seemingly "killing" Andrea remains one of the most peculiar and unsettling scenes in Mad Men.

Sylvia Rosen

Lee Cabot

Don surprisingly remained faithful to Megan in the early part of their marriage during Mad Men season 5. However, by season 6, Don reverts back to his old habits and begins an affair with his neighbor, Sylvia Rosen. Sylvia, who is married to Don's friend Dr. Arthur Rosen, carries on the affair with Don right under Megan and Arthur's noses. Their illicit relationship continues until Sally unintentionally discovers her father engaging in a sexual encounter with Sylvia, effectively putting an end to their affair.

Contrary to popular belief, Lee Cabot (Neve Campbell) is not considered one of Don Draper's mistresses and he did not engage in an affair with her. Their paths cross during a late-night flight from Los Angeles to New York in the premiere of Mad Men's seventh season. Draper undeniably feels a strong attraction towards Lee, a well-to-do widow, and they share an intimate journey home on the plane. However, upon arriving in New York, Don declines Lee's offer to "share a cab" together.

Amy

Amy (played by Jenny Wade, known for her roles on American Horror Story) is a close friend of Megan's in California. Megan, after leaving New York and relocating to Hollywood to follow her acting dreams, got to know Amy. Following a party at Megan's place, Don's estranged wife extends an invitation to him, proposing a threesome involving herself and Amy.

Tricia

Tricia (Kirstin Ford) is not just one of Don Draper's many mistresses, but also another flight attendant whom Don met when he regularly flew to LA to visit Megan during Mad Men season 7. Tricia contacted Don's answering service and informed him that she was in town. When Don invites her to his apartment, Tricia accidentally spills red wine on his white carpet.

Diana Bauer

While spending the evening with some female companions in the town, Don becomes captivated by a waitress at a diner whom Draper believes he had previously encountered. The waitress goes by the name of Diana Bauer (played by Elizabeth Reaser from The Haunting of Hill House) and it is revealed that she is a deeply melancholic woman who had abandoned her son in the Midwest. When she mysteriously disappears, Don embarks on a journey to Wisconsin in an attempt to locate her. As the Mad Men series approached its conclusion, Diana's presence in Don's life appeared to be an unconventional fixation, yet it served as a driving force for Draper as he departed from New York and ventured towards the ultimate conclusion of the show.

Eve

In the series finale of Mad Men, Eve (played by Fiona Gubelmann) becomes the final mistress of Don Draper. While on his journey to California, Don engages in car racing and ends up sleeping with Eve, a local woman. Despite her attempt to steal his wallet, Don catches her and still gives her money. It is highly likely that even after the conclusion of Mad Men, Don continued his pattern of infidelity, especially if he returned to New York to resume his advertising career.

Which Of His Mistresses Should Don Have Ended Up With

Don Draper from Mad Men was known for his numerous extramarital relationships, but these affairs never provided a solution to his problems. In fact, many of the women involved benefited when Don chose not to reenter their lives. However, Suzanne, Sally's teacher, could have been an exception as she seemed to genuinely care for Don and possessed a certain innocence. Another potential candidate was Rachel Menken, a mistress with whom Don shared undeniable chemistry and was honest about his true identity. Despite these possibilities, none of these women were viable long-term options, and Don Draper in Mad Men frequently faced the consequences of his actions.

Editor's P/S

As a Gen Z netizen, I have mixed feelings about Don Draper's womanizing behavior. On the one hand, I understand that he is a product of his time and that the social norms of the 1960s were different from those of today. On the other hand, I find it difficult to condone his behavior, especially given the pain and suffering he caused his wives and children.

I think it's important to remember that Don Draper is a complex character, and his womanizing behavior is just one aspect of his personality. He is also a talented advertising executive, a loving father, and a loyal friend. Ultimately, I believe that Don Draper is a cautionary tale about the dangers of letting our desires get the best of us.