Relationships and love aren’t necessarily focal points of Mad Men, but that doesn’t mean that it plays no part in the show at all. Even though the show’s main focus is on the men of the show building their careers, their love lives become a major part of that.
Whether it is the loyal family man or the cheat, the ensemble cast of characters really does have it all. Some of the relationships in the show are heartwarming and the fans quickly got behind them. However, for every perfect couple, there was another that made absolutely no sense. Whether they were in a relationship for the status or simply because they couldn’t be without one, there were some ridiculous relationships on the show.
10 Best: Peggy & Stan
One of the best relationships from Mad Men comes later on in the series as Peggy and Stan slowly end up together. It is something Peggy desperately deserves, as she goes through her fair share of poor romances in this show, although nobody would have predicted this relationship early on.
Stan and Peggy actually start out hating each other and they slowly develop a friendship and then a relationship. It is perhaps through that slow burn that it is clear they just click and deserve to be together as they are able to counterbalance each other’s negatives. We only find out that they love each other in the finale, so how they actually are as a couple is unknown. However, at this stage in their lives, it feels like they are ready to commit to this and fingers crossed, it would work.
9 Worst: Roger & Jane
Roger has a few relationships during the course of the show, but the worst of them has to be his marriage to Jane. The entire thing just feels very desperate and like Roger is trying to remain as youthful as possible, which isn’t helped by the fact that Jane is quite an annoying character in general.
It is clear right from the start that this marriage is doomed as Roger has no ability to actually be faithful. They just never seem to have much in common which made the couple seem very strange in the first place, with plenty of arguments taking place between them.
8 Best: Roger & Joan
They might never end up together officially, there’s no doubt that Joan and Roger have a lot of love together and their relationship (if you can call it that) is a great one. This is the relationship that Roger desperately wants to have, but never has the guts to make official.
Instead, the duo just has a decade long affair, but it’s not all about the sex for them as they clearly have feelings for each other as well. They do balance each other quite well, with Joan being able to calm down Roger’s erratic decisions. Yet, sadly, they never manage to actually make it work in a real relationship.
7 Worst: Don & Betty
When we are first introduced to the Drapers they are presented as the ideal American family. A beautiful couple with cute children, successful work and a lovely home, it seemed to be perfect, however, the only issue with that was the fact Don was cheating on Betty as often as possible.
Despite Betty being a loving and beautiful wife, Don seemed to just have no care about her at all. Perhaps at one stage before the show, they were a fantastic couple, but they don’t appear to have that much in common and Don’s actions end up having a terrible effect on Betty as a person. The constant affairs really mess up her mental health, with his decision to belittle her at every opportunity not helping matters either. It feels like a relationship that Don needs as a front to appear in a certain way rather than for love.
6 Best: Henry & Betty
While Betty’s relationship with Don is clearly never going to work, one couple that is obviously right for each other is her second marriage to Henry. Because both of them are heading into their second marriage, they appear to know exactly what they want from life, which makes them work well together.
Henry takes to the children very well, and, unlike Don, actually wants to spend time with them. It is clear that he cares deeply for Betty and isn’t set to cheat on her at every given moment as her ex-husband did, and finally, Betty gets the sort of relationship she deserves.
5 Worst: Pete & Trudy
Like many of the men on this show, Pete struggled with keeping it in his pants and constantly cheats on his partner, Trudy, which is a real shame. Trudy is one of the nicest women on the show, she clearly loves Pete and tries her best to make him happy but it simply isn’t good enough.
Pete’s eye is constantly drifting on whatever he can find away from his wife, which makes them a dreadful couple in reality. It is a shame that things don’t work out different for them, as, at times, they seem like a great couple, such as their dance routine at Roger’s wedding. But, ultimately, Pete’s inability to behave makes this a doomed relationship.
4 Best: Don & Faye
Don Draper has many relationships and flings throughout the show, including two marriages, and none of them ends up working. It is clear that he’s just a serial womanizer and he isn’t going to change his habits, but the one woman who had the potential to was Faye Miller.
Due to Faye’s line of work, she was able to really understand Don, unlike any of his other partners. She was able to analyze him and work out exactly what he was doing wrong. Sadly, rather than trying to tackle the relationship and Don’s issues, Faye saw all the potential problems and opted out.
3 Worst: Peggy & Duck
Duck is a character that goes through a lot of ups and downs throughout his time on Mad Men and clearly struggles mentally whenever things do not go his way. That is why it is immediately clear that he and Peggy are not a relationship that will sustain.
Both of them are highly strung and are so focused on their work that they aren’t always able to focus on love and who they’re committed to. Duck constantly pushes too hard to make this relationship work while Peggy is trying to build her career, and the entire thing just feels off from the start.
2 Best: Ken & Cynthia
Ken Cosgrove’s relationship with Cynthia isn’t exactly featured heavily, but the main reason for that is because there’s no drama in that relationship. The two of them go about their lives normally like a happy couple and do everything they can to help each other.
It is clear that they love each other when they do appear and that makes them one of the best couples on the show. Ken is a loveable character on the show who is incredibly well-liked by most, which is why this duo is a perfect relationship in this crazy world.
1 Worst: Joan & Greg
The worst couple of the entire series is Joan’s relationship with Greg as it makes absolutely no sense at all. While everything on the surface makes them seem like a perfect couple, with Joan portraying that they are the ideal couple on the outside, on the inside everyone knows it is a horrible relationship.
Joan is normally in control of every situation and doesn’t allow herself to be taken advantage of. Yet, in this relationship, she stays with a monster who manipulates her, rapes her, and treats her terribly, which is why it makes absolutely zero sense. The fact that they end up taking their relationship as far as marriage makes it even worse. With Greg taking his failing medical career out on her, the only good moment here is when Joan smashes him around the head with a vase.