'Mad Men's Don Draper's many wives, girlfriends and one night stands

June 12, 2024

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Betty Draper
Played by: January Jones
Seen in: Seasons 1-7
Who she is: A former model, Don’s first wife acts as his charming and loving spouse at important client dinners, but at home Betty is cold, sometimes cruel and deeply unhappy in her role as the typical American housewife. She's also unaware of Don’s dark past until she stumbles across a secret drawer in season 3 and confronts him about his lies. She finally extricates herself from their relationship and marries politician Henry Francis (Christopher Stanley), but although Henry is a much better husband than Don will ever be, Betty still isn’t happy. Despite their new spouses, there’s still chemistry between Don and Betty, as evidenced by the fact that they sleep together while visiting their son at camp in season 6.
How they left off: Divorced but civil
Read more: Mad Men: THR's Full Coverage
Midge Daniels
Played by: Rosemarie DeWitt
Seen in: Season 1 & 4
Who she is: At the beginning of the series, Don often leaves work early to spend lazy afternoons with Midge, a beatnik illustrator and painter who rejects traditional concepts of domesticity and marriage. In typical Don Draper fashion, he invites her to run away with him to Paris in “The Hobo Code” but she refuses. Don later meets up with her in season 4 when Midge, now married to a failed playwright and a heroin addict, seeks him out to buy one of her paintings, which Don does out of sympathy.
How they left off: Midge rejects his proposal to run away to Paris
Read more: The Uncensored, Epic, Never-Told Story Behind 'Mad Men'
Rachel Menken
Played by: Maggie Siff
Seen in: Season 1 & 2
Who she is: Smart, classy and bold, Rachel is the head of a major Jewish department store and meets Don when she comes to Sterling Cooper seeking advertising advice. Don becomes completely enamored with her and although she initially resists his advances because of his marital status (which Don fails to reveal until after their first kiss), she eventually succumbs to his charms. Don proposes they run away together — this time to Los Angeles — but she can see right through him. “You don’t want to run away with me,” she tells him. “You just want to run away.” Don and Rachel meet again in the second season when she introduces him to her new husband.
How they left off: Rachel refuses to run away to Los Angeles with him
Joy
Played by: Laura Ramsey
Seen in: Season 2’s “The Jet Set”
Who she is: While on a business trip to Los Angeles, Don meets free-spirited Joy at the pool bar, who convinces him to abandon Pete (Vincent Kartheiser) and drive with her to a friend’s fancy house in Palm Springs. They spend the next few days swimming, romancing, sunbathing and playing party games with her wealthy European friends.
How they left off: Don leaves Joy to visit Anna Draper and then returns to New York
Read more: Mad Men – Review, Final Season
Bobbie Barrett
Played by: Melinda McGraw
Seen in: Season 2
Who she is: The wife and manager of comic Jimmy Barrett, Bobbie meets Don for damage control after her husband insults the Utz Potato Chips owner’s wife, for which he acts as the spokesman. Later at dinner when Bobbie tries to blackmail $25,000 out of Don in exchange for Jimmy’s apology, Don violently assaults her. The remainder of their unhealthy relationship includes a drunken car crash while driving to Bobbie’s beach house on Long Island, with Don having to call Peggy to come bring them money to pay the fines. Bobbie stays at Peggy’s apartment to recover and gives her some life advice, “No one will tell you this, but you can’t be a man. Don’t even try. Be a woman. Powerful business when done correctly.”
How they left off: Don breaks it off when he finds out Bobbie has been gossiping about his reputation in bed
Anna Draper
Played by: Melinda Page Hamilton
Seen in: Seasons 2 & 4
Who she is: Anna Draper might not be one of Don’s many romantic conquests, but their unique relationship merits her inclusion. The true wife of Lieutenant Donald Draper, Anna and Don formed a deep bond after her real husband died in the Korean War and Dick Whitman (Don’s real name) assumed his identity. Keeping a rare platonic relationship, Don often visits Anna in California and continues paying her expenses even after he divorces her to marry Betty. When Don learns of Anna’s death from terminal cancer in season 4’s powerhouse episode “The Suitcase,” he reveals to Peggy in an unprecedented example of transparency that Anna was “the only person in the world who really knew me.”
How they left off: Anna passes away in season 4
Read more: 'Matthew Weiner's Mad Men': Exhibition Review
Shelly
Played by: Sunny Mabrey
Seen in: Season 3’s “Out of Town”
Who she is: Don meets Shelly the stewardess while flying on a business trip to Baltimore with Sal (Bryan Batt) in the first episode of season 3. The two say their names are “Bill” and “Sam” and telling everyone they’re accountants investigating Jimmy Hoffa for embezzlement. After the flight and a flirtatious dinner with the stewardesses, Shelly tells Don in the hotel hallway that she’s engaged and he reassures her by saying, “I’ve been married a long time. You get plenty of chances.” Shelly disappears after the fire alarm goes off and Don gives her pin-on wings — the only record of the tryst — to Sally (Kiernan Shipka) when he returns home.
How they left off: One night stand
Suzanne Farrell
Played by: Abigail Spencer
Seen in: Season 3
Who she is: Sally’s idealistic teacher is initially hesitant about an affair with Don but he charms her, helping out with a class lesson at the park and giving her a lift home after her early morning jog. Don tells Suzanne he can’t stop thinking about her and she admits the same, although she says she knows how things will end with Don. “So what?” he replies and kisses her. Their happiness is interrupted when Suzanne’s epileptic brother, Danny, shows up one night and Don volunteers to drive him to a new job in Massachusetts, although in reality he drops him off on the side of the road with cash and his business card after Danny reveals he has no intention of working. Don and Suzanne’s plans to go on vacation while his family is away are dashed when Betty and the kids return home early and Betty finds Don’s stash of memorabilia from his past.
How they left off: Don ends it after Betty confronts him about his true identity
Read more: What's Next for the Mad Men (and Women)?
Candace
Played by: Erin Cummings
Seen in: Season 4’s “Public Relations” and “The Good News”
Who she is: Candace is a call girl whom audiences are introduced to when Don hires her for a rough session on Thanksgiving Day, although it’s assumed that they’ve known each other a while. She reappears a few episodes later, when Don and Lane (Jared Harris) go out on the town so that Don can cheer up Lane about his broken marriage.
How they left off: Prostitute for hire
Allison
Played by: Alexa Alemanni
Seen in: Season 1-4
Who she is: Allison works as a secretary around the office before she lands at Don’s desk. She’s competent, attentive and even buys his children’s Christmas presents. Their relationship stays professional until Don returns to his apartment drunk and sans keys after the holiday party and calls Allison to deliver them. The two sleep together and Allison is thrilled until the next day, when Don doesn’t acknowledge their night and hands her an envelope with $100, claiming it’s the Christmas bonus they had talked about. Allison eventually becomes so frustrated with Don that she tells him he’s not a good person and hurls a paperweight at his head, fulfilling the fantasy of every woman Don Draper has ever jilted.
How they left off: She resigns after their one night stand
See more: Mad Men: Exclusive portraits of the cast
Bethany Van Nuys
Played by: Anna Camp
Seen in: Season 4
Who she is: Out of all of Don’s ladies throughout the years, Miss Bethany Van Nuys is arguably the most boring. In a post-Betty but pre-Megan period, Don briefly dates Bethany, a beautiful but dull aspiring actress friend of Jane Sterling’s (Peyton List). After a few polite dinners, Don can no longer ignore their lack of chemistry and whatever attraction there might have been fizzles out.
How they left off: After a couple of dates, Don ends their courtship
Doris & Alice
Played by: Becky Wahlstrom & Amy Motta
Seen in: Season 4’s “Waldorf Stories”
Who they are: After winning the Clio for his Glo-Coat commercial and getting rebuffed by Faye (Cara Buono), Don parties the night away in one of his typical downward spirals. He goes to bed with a woman whom he met at the bar, Alice, and wakes up thoroughly confused next to Doris, who calls him by his real name. Don makes up some half-hearted excuse to kick her out, showers and then — to nobody’s surprise — pours himself another drink.
How they left off: One night stands
Read more: Mad Men: THR's Full Coverage
Dr. Faye Miller
Played by: Cara Buono
Seen in: Season 4
Who she is: Whip-smart and accomplished, Faye is a consultant for a consumer-research company hired by the agency and arguably the most solid and supportive of Don’s relationships. She’s modern and career-focused and like Rachel Menken before her, initially hesitant of Don’s advances. Faye is one of the few women to whom Don reveals his mysterious past after he suffers a panic attack and she comforts him. When he tells her about his engagement to Megan, she tells him that she hopes his fiancée knows that he only likes “the beginning of things.”
How they left off: Don breaks up with Faye after he proposes to Megan
Megan Draper
Played by: Jessica Paré
Seen in: Season 4-7
Who she is: Megan starts off as another one of Don’s secretaries but then quickly becomes his current wife after Don impulsively proposes to her while she takes care of his kids on a trip to California. Paré told The Hollywood Reporter,“When Megan and Don kiss for the first time, everybody on set was like, ‘Well, it's been great to have you around, Jessica. You'll be on your way out now.’ That's how things had been going. But Matt [Weiner] called me a few days before and told me Don was going to propose. I had a hint before that: Ellen, our props master, came into my dressing room and said, ‘You can’t ask me any questions about it, but I need to measure your ring finger.’”
How they left off: Don offered to come live with Megan in Los Angeles, but she refused. More to come?
Read more: Mad Men: THR's Full Coverage
Andrea Rhodes
Played by: Mädchen Amick
Seen in: Season 5’s “Mystery Date”
Who she is: Now newlyweds, Megan and Don meet Andrea in the elevator and it’s immediately evident by Andrea’s relentless flirting that she and Don have a history. Later, a sick Don has vivid fever dreams that he and Andrea sleep together. When dream-Andrea returns for a second time, Don tells her their tryst was a mistake, knocks her to the floor and chokes her until she stops moving. Then he pushes her body under the bed. A panicked Don awakens to Megan bringing him a breakfast tray and Andrea’s body is nowhere to be found.
How they left off: It was only a dream
Sylvia Rosen
Played by: Linda Cardellini
Seen in: Season 6
Who she is: Sylvia and Arthur Rosen (Brian Markinson) are Megan and Don’s neighbors and friends, which makes it that much worse when Don and Sylvia began having an affair. They both feel guilty but continue, Don visiting Sylvia’s apartment while her husband is at work. Sylvia eventually tries to end the affair, but an obsessive Don loiters and smokes outside of the Rosen’s service entrance for days and they start back up again. Their relationship comes to a screeching halt after Sally catches them in the act.
How they left off: The affair ends after Sally catches them
Read more: The Uncensored, Epic, Never-Told Story Behind Mad Men