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

Mad Men: 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.

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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,…

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