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12 Women Don Almost Loved (& Why It Didn’t Work Out)


It’s hard to think of a more visually appealing TV show than Mad Men. From the fashionable workplace outfits to Don Draper enjoying cocktails in his office, all of the characters have an incredible sense of style, and every episode feels like a mini-movie. While Don is definitely a unique protagonist, he doesn’t succeed in the love department since he isn’t capable of having real feelings for someone. Throughout all seven seasons of the show, Don dates many people, proving that the Mad Men cast is full of fascinating characters, even if they are only part of a few brief storylines.

When wondering who did Don Draper really love, Rachel Menken comes to mind, along with some others who have been part of his journey. Fans of the show know that Don can’t really sustain a loving, healthy relationship, but there are some moments when he comes close to falling in love.


Updated on June 23, 2022 by Aya Tsintziras: While Mad Men ended in 2015, the drama is still celebrated and appreciated for its strong characters and plotlines about advertising. Don Draper’s complicated love life is always a big feature of each episode, and there are some Mad Men women who he almost cares about. 


mad men joy

Don and Joy meet in L.A. and these two don’t really get a chance to explore a relationship, but Joy still feels like a fairly significant part of the series.

RELATED: 10 Mad Men Couples That Would Have Made A Lot Of Sense (But Never Got Together)

If Don lived in California, it’s possible that he and Joy would have dated and maybe he would have fallen for her, as he finds her interesting and beautiful. The problem with them is that Don likes the promise and potential of a shiny new person but once he gets deeper into the relationship, he gets scared of being himself and runs away.

Bethany Van Nuys

Many of the best Mad Men characters only appear in one episode. Bethany Van Nuys appears ina few, but she makes a big impression.

Bethany is pals with Roger Sterling’s wife, Jane, and agrees to go out with Don in season 4. Things fizzle out pretty naturally as these two don’t spend much time together, and she wises up to the fact that Don never wants to commit to just one person.

Faye Miller

Don dates Faye when he meets her at the office, as she works as a strategist for a research company. She first appears in the season 4 episode “Christmas Comes But Once A Year.”

Don and Faye’s relationship is an interesting one as he actually tells her who he really is, which fans never expected him to do with anyone. While Don comes close to loving Faye as he might be able to be himself with her, he decides to marry Megan instead. Faye is a brilliant and wise character who tells Megan that Don is happy when he’s starting a new romance since it’s fresh, shiny and new but he will get tired of her… which does happen.

Suzanne Farrell

mad men suzanne

Don dates Sally’s teacher, Suzanne, briefly, and she can read him like a book. This relationship is yet another reminder that Don cares about his personal life more than his family.

RELATED: 10 Movies To Watch With The Cast Of Mad Men, Ranked According To IMDb

Suzanne knows a few things about Don, from how depressed he is to the fact that their love story has no future. She’s an intelligent woman who’s always one step ahead of him.

Sylvia Rosen

Don’s mistress in season 6, Sylvia Rosen is a fascinating character as she has a conscience and doesn’t want Don’s marriage to Megan to be ruined because of her.

One of Sylvia’s most memorable moments is when she has a nightmare about helping Megan with her grief after Don dies in a plane crash, and that ultimately makes her realize she should stop sleeping with him. Don is upset when Sylvia ends their romance, which suggests that he could almost love her, but fans can tell that Don has trouble with rejection as he likes to be the one in control.

Betty Hofstadt Francis

Don and Betty seem like they’re doing okay in season 1, but it soon becomes clear that they have a lot of problems in their marriage. She goes to therapy and lets her therapist know that she isn’t in the dark about the other women that Don is sleeping with, as she can tell that the therapist is sharing everything with Don.

Near the end of the show, it’s revealed that Betty is dying of lung cancer. While Betty can be harsh and Mad Men fans think Betty gets worse as a character, there are moments when Don seems like he really loves her, and it makes sense why they were drawn to each other in the first place. Don isn’t capable of being a happy family man but he does try, and Betty ultimately realizes that she will never get the emotional connection that she needs from him.

Rachel Menken

Rachel Menken runs Menken’s Department Store and to her, it’s crucial that she has a career. Don doesn’t really care about her, as he wants her to move to L.A. with him while she recognizes that he’s hiding from his life and his problems. She’s too intelligent to fall for Don and fans can tell that since he isn’t honest about who he is, they could never work out.

Rachel is a refreshing character, as she has an important career when so many of her peers are told they can only be secretaries. When Don learns that she died, he’s definitely upset, which hints at what could have been.

Anna Draper

One of the most compelling aspects of Don’s story is the fact that he steals another man’s name. The real Don Draper’s wife, Anna, is incredibly kind and compassionate; after she finds out that Dick Whitman stole her husband’s identity, she even becomes pals with him.

RELATED: The Main Mad Men Characters, Ranked By Wealth

It’s obvious that Don truly cares for Anna and it seems like this is only possible because of the platonic nature of their relationship. She is truly the most important person in his life.

Midge Daniels

mad men midge and don

Even though Midge has a sad return in season 4, as she’s addicted to drugs and her marriage isn’t working out, her appearance at the beginning of the show cements her as a strong contender for Don’s heart. Midge is one of Don’s most memorable Mad Men love interests.

While they aren’t together for very long, Midge has a great free-spirited attitude and bohemian sense of style. She doesn’t need to be Don’s wife and she has no problem standing up to him. Things would never work out because she doesn’t want a commitment, in contrast to some of the other people in Don’s romantic world.

Megan Draper

Megan has always stylish clothing and she makes a splash from the moment she first appears onscreen.

Megan and Don’s love story is a compelling one. She isn’t content to sit on the sidelines or let Don fool around with other women while still married to her. Even though she wants to be free and independent, Megan still tries to be a good role model for Don’s children. She wants to follow her acting dreams, but when she can’t get any traction, she realizes that she and Don aren’t meant to be. While they attempt a long-distance marriage, they’re both miserable.

Bobbie Barrett

Don meets Bobbie when her husband, comedian Jimmy Barrett, does some work for Utz Potato Chips. Don and Bobbie begin secretly seeing each other.

They are part of one of Mad Men‘s most shocking moments as they get into a car crash. While their time together is brief, Bobbie is someone who Don could potentially love if she wasn’t married and if they could get to know each other for real.

Andrea Rhodes

Andrea - Mad Men

Andrea’s time on Mad Men is very different from his other love interests. They used to date, and in the season 5 episode “Mystery Date,” Don has a dream that he killed her.

This is a frightening scene and says a lot about Don’s state of mind. Don is often terrified of being on his own and he sabotages his relationships by cheating and not being vulnerable or honest. Don realizes that he and Andrea could have had something real, if only he had opened up his heart.

NEXT: 10 Mad Men Characters Who Appear The Most In The Series

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