Mad Men: 10 Characters Joan Holloway Should Have Ended With

Joan Holloway is one of Mad Men’s most compelling characters and someone who fans absolutely loved. She is very confident and has a huge role to play within the agency which allows her to become one of the main characters in the series.

However, despite her confidence and looks, Joan does actually struggle in the world of love. She does get married on the show, but sadly he turns out to be one of the worst characters of the entire series. She has no shortage of offers from people, but things just don’t work out and in the end, Joan finishes the series single.

While she ends up in a position of power as she begins setting up her own business where she will answer to nobody, it’s a shame she doesn’t find true love. Within this list, we will take a look at 10 characters Joan should have ended up with.

10 Richard

Richard joins the show much later on in the series but immediately hits it off with Joan and they get into a relationship together. The two of them really connect with Richard clearly falling for Joan. He can offer her an amazing life that is relaxed and full of travel as he is happily retired and rich.

However, she chooses to pursue business and sticking with work instead of ending up in a relationship with him. It’s a real shame they don’t work out though, as Richard is a very nice person who clearly treats Joan well and perhaps they could have worked out a way to be together.

9 Lane Pryce

Obviously, for this relationship to have happened a major change would have been needed in Lane Pryce’s storyline. He does commit suicide during the show, so that would’ve had to be altered, however, he was an incredibly popular character so fans wouldn’t have complained about him sticking around longer.

Lane and Joan did share a great bond together, mainly because their jobs were similar. Both of them felt slightly underappreciated and wanted to have their own accounts. Lane made a pass at Joan several times but never quite got his dream woman, although they could have been great together.

8 Duck Phillips

Herman ‘Duck’ Phillips is a supporting character who makes appearances throughout the show and is someone who has a major problem with drinking. When he is fired things begin spiralling out of control for him, but it would have been an ideal way to end things by having Duck recover to be with Joan.

Is he the perfect man for Joan? Perhaps not, but he can be a nice man as he proves whenever he isn’t drunk. With his contacts and Joan’s pure desire, they could have done some good business together if they got the chance.

7 Henry Francis

We never really see Joan Holloway in the setting that the likes of Betty Draper and Trudy Campbell have to be in. Going on dates to impress their husband’s clients, but there’s no doubt with her ability to flirt and persuade she would have impressed and caught people’s eye in this world.

That’s why she and Henry Francis could have been great together. This would have meant Henry not being with Betty, but that could have worked with a different character taking that role. Henry knows how to treat a woman well, which is something that Joan does deserve.

6 Stan Rizzo

Stan Rizzo is someone who everyone in the office seems to love. He is funny, charming, and has an amazing personality, however he doesn’t interact too much with Joan. That’s a shame as the two of them could really have clicked if the storyline had allowed.

Had that happened, there’s no doubt that Stan and Joan would have hit it off, and while it would have been a shame that Peggy could have ended up alone, it would have been fun to see this pair together.

5 Ted Chaough

Ted Chaough’s interest in Peggy Olson ends up having a major impact on his marriage, which is why he also ends up alone by the end of Mad Men. However, even though he doesn’t end up in a relationship with anyone, Ted does get his happiness back by simply becoming a cog on the wheel.

He enjoys having less pressure on his job and that allows him to be back to his confident and cheerful self. That’s why in the end, he and Joan would have been great together as they are both in great places and ready to be happy in their lives.

4 Ken Cosgrove

Ken Cosgrove is the resident ‘Mr. Nice Guy’ of Mad Men. Unlike other characters on the show, he isn’t busy cheating on his wife or drinking all the time and that is why he would have been great to end up with Joan. He isn’t given as much attention as other characters, and a relationship with Joan could have provided that.

Ken is the exact type of person that Joan does deserve, as she is treated incredibly poorly at times in her life. Being able to end with an honest man who is actually looking out for her would certainly have been fitting for such a big character like Joan.

3 Bob Benson

A relationship with Bob Benson would certainly have been possible for Joan Holloway as he actually proposed to her during the series. He makes it clear that he would like to be there for her to provide for her and look after the family, but the reality is that Bob is actual homosexual, and therefore can’t provide everything for her.

Bob wants to use the relationship as a cover-up for himself, while they could both see other people. While it doesn’t exactly sound perfect, it could have made life a little easier for Joan in terms of providing for her family, plus they did get along very well.

2 Don Draper

From a purely aesthetic perspective, a relationship between Don Draper and Joan Holloway could have been absolutely perfect. On top of that, Don and Joan are always great when they’re together. They have fun and treat each other with respect, clearly being attracted to one another.

However, they don’t end up ever coming close to being romantic, which felt like a missed opportunity. Both of them were looking for something different and searching to be accepted in different ways, therefore finally putting them together could have been a brilliant way to end the show.

1 Roger Sterling

Without a doubt, the person that Joan Holloway should have ended up in a relationship with is Roger Sterling. The two of them have a great friendship together and they do share a romantic bond early on in the show, with Roger cheating on his wife with Joan.

The two of them end up stopping their fling, although they have one more night which leads to them having a child together. Bringing them together as an official couple would have felt like a perfect way to wrap things up for both of them, as their secret relationship is one that fans loved.

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