Food Men: 12 Women Don Almost Loved (and Why It Didn’t Succeed)

It’s hard to think of a more visually appealing TV show than Mad Men. From trendy workwear to Don Draper enjoying cocktails in his office, all the characters have an incredible sense of style, and each episode feels like a mini-movie. Although Don is certainly a unique protagonist, he fails in the love department as he is unable to have real feelings for anyone. Throughout the series’ seven seasons, Don dates many people, proving that the cast for Mad Men is filled with fascinating characters, even though they’re only part of a few short plots.

When one wonders who really loved Don Draper, Rachel Menken comes to mind along with others who have been a part of his journey. Fans of the show know that Don may not quite be able to maintain a healthy, loving relationship, but there are times when he’s on the verge of falling in love.

Updated June 23, 2022 by Aya Tsintziras: While Mad Men ended in 2015, the drama is still celebrated and appreciated for its strong characters and stories of publicity. Don Draper’s complicated love life is always a big part of every episode, and there are Mad Men women he almost loves.


Don and Joy meet in Los Angeles, and these two don’t really get to explore a relationship, but Joy still feels like a pretty big part of the show.

If Don lived in California, it is possible that he and Joy were dating, and he may have fallen in love with her because he finds her interesting and beautiful. The problem with them is that Don loves the promise and potential of a bright new person, but once he deepens the relationship, he is afraid of being himself and runs away.

Bethany Van Nuys

Many of Mad Mens’ best characters appear in only one episode. Bethany Van Nuys performs in a few pieces, but she makes a good impression.

Bethany is friends with Roger Sterling’s wife, Jane, and agrees to go out with Don in season 4. Things happen quite naturally as these two do not spend much time together and she realizes that Don will never commit. to one person.

Faye Miller

Don dates Faye when he meets her in the office as she works as a strategist for an analytics firm. She appears for the first time in the season 4 episode “Christmas Comes But Once A Year”.

Don and Faye’s relationship is interesting because he actually tells her who he really is, which fans did not expect him to do with anyone. Since Don is falling in love with Faye because he could be himself with her, he decides to marry Megan instead. Faye is a bright and clever character who tells Megan that Don is happy when he starts a new romance because it is fresh and bright and new, but he gets tired of her … which happens.

Suzanne Farell

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

Suzanne knows a few things about Don, from his depression to the fact that their romance has no future. She is a wise woman who is always one step ahead of him.

Sylvia Rosen

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

One of Sylvia’s most memorable moments is the nightmare, where she helps Megan work through her grief after Don’s death in a plane crash, which eventually makes her realize that she should stop sleeping with him. Don is upset as Sylvia ends their romance, suggesting that he might almost love her, but fans can tell that Don is struggling with rejection because he enjoys being the one in control.

Betty Hofstadt Francois

Don and Betty seem to be doing well in season 1, but it quickly turns out that they have a lot of problems in their marriage. She goes into therapy and lets her therapist know that she is not in the dark about the other women Don sleeps with, as she can tell that the therapist shares everything with Don.

Near the end of the show, it is revealed that Betty is dying of lung cancer. While Betty may be tough, and Mad Men fans think Betty is getting worse as a character, there are times when Don seems to really like her, and it makes sense that they were attracted to each other first. Don is not able to be a happy family man, but he tries, and Betty eventually realizes that she will never get the emotional connection she needs from him.

Rachel Menken

Rachel Menken runs the department store Menken, and for her it is crucial that she has a career. Don does not care about her as he wants her to move to LA with him as she acknowledges that he is hiding from her life and problems. She’s too smart to fall for Don, and fans can tell that since he’s not honest about who he is, they could never train.

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 finds out she’s dead, he’s definitely upset and suggests 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. Don Draper’s real wife, Anna, is incredibly kind and compassionate. after discovering that Dick Whitman stole her husband’s identity, she even becomes friends with him.

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

myg daniels

Although Midge has a sad comeback in season 4, as she is addicted to drugs and her marriage does not work, her appearance early in the series cements her as a serious challenger to Don’s heart. Midge is one of Don’s most memorable Mad Men love interests.

Although they have not been together for quite some time, Midge has an amazingly liberal attitude and a sense of bohemian style. She does not have to be Don’s wife, and she has no problem standing up to him. Things would never work out because she does not want a commitment, unlike some of the other people in Don’s romantic world.

Megan Draper

Megan always has stylish clothes and she evoked a sensation from her first appearance on screen.

Megan and Don’s love story is fascinating. She does not just sit on the sidelines or let Don have fun with other women while she is still married. Although she wants to be free and independent, Megan always tries to be a good role model for Don’s children. She wants to follow her acting dreams, but since she can not get traction, she realizes that she and Don are not meant to be. When they try a long distance marriage, they are both miserable.

Bobbie Barrett

Don meets Bobbie as her husband, comedian Jimmy Barrett, works for Utz Potato Chips. Don and Bobbie begin to see each other in secret.

They are part of one of Mad Men’s most shocking moments when they come across a car accident. Although their time together is short, Bobbie is one Don could potentially love if she was not married and they could get to know each other for real.

Andrea Rhodes

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

It’s a shocking scene that says a lot about Don’s state of mind. Don is often afraid of being alone and he sabotages his relationships by cheating and not being vulnerable or honest. Don realizes that he and Andrea could have gotten something real if only he had opened his heart.

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