Mad Men: 10 Short-Term Love Interests Who Deserved More

Mad Men was all about testing the limits and crossing the lines, and the love stories in the show were no exception. The show didn’t adopt the usual utopia-like romances you see on TV. Everything was real and every character was allowed to follow their heart, even when it hurt another character. It is hard to tell which of the characters were really in love with their primary partners, but some of their short-term interests definitely deserved a real shot.

Love and loss don’t get any sweeter than in Mad Men, where the line between love and a mess is so slim. From Don, a drunkard and a womanizer with countless lies to his name, to Pete, a lonely man struggling to be accepted both at home and in the office, Mad Men simply had the best combination of complicated relationships, some deserving a few more tries than they got.

10 Don & Midge

Midge Daniels ended the show badly, hooked on heroin and struggling to make ends meet, which was the exact opposite of the Midge that fans met in the first season who was all over Don Draper. She was mature and realistic and probably the only person that offered Don a way out of his messed life in New York. What she and Don had was more real than most of Don’s other mistresses.

Neither Don nor Midge were willing to give up their other relationships for what they felt for each other, though, leading to the relationship’s death. Midge didn’t love Don for his money. She was also the only person that understood his struggles and would have probably made a better partner when things got tough for him.

9 Don & Sylvia

Sally loved and respected Don until the day she walked in on him in bed with Sylvia, which was shameful, but that doesn’t mean the relationship was all bad. Sylvia breaking up the affair was the right decision at the time because both were married, and their partners were friends, but it was sad to watch them break up. For the first time in Don’s history of womanizing, Don was heartbroken.

While it seemed like just another short-lived romance at first, Don was no longer in love with his wife, and he may have truly loved Sylvia. He even went out of his way to pull off the perfect trick to get Sylvia back in bed with him. It was not like Don to make sacrifices for women he didn’t love, and it was obvious that Sylvia loved him, too.

8 Duck & Peggy

Herman “Duck” Philips was hired mostly to put Pete in his place, but it only served to sweep Peggy off her feet. Or Duck, depending on how you look at it. The two had one of the most natural chemistries of any couple in the show, but their relationship never had a chance. They were both ambitious and working in a toxic environment where love couldn’t thrive.

Duck’s problems also caught up with him before he could explore his feelings for Peggy, further leaving him to sink into depression and alcoholism. When Duck returned to Peggy, she was already gone, and Duck was in no position to date anyone. However, if they explored it earlier while they were both into each other, it would have been perfect.

7 Pete & Peggy

Pete and Peggy were the perfect couple that fell in love at the wrong time. Pete was just getting married and Peggy couldn’t do anything about that. Pete was also a proud guy in season one who didn’t want to be seen dancing with Peggy and who would rather please his family and the boys rather than confess his feelings.

He later dropped his pride and confessed his feelings to Peggy, but she was no longer the timid secretary that could be intimidated, and so the scores were even. If they met earlier, or Pete dropped his pride earlier than he did, they would have made a great couple.

6 Roger & Joan

Roger and Joan were a mature couple that knew they liked each other but that taking the next step would ruin their work and family lives. They were both go-getters who knew how to have their cake and eat it too, although it wasn’t all good.

Joan settled for an unhappy marriage with Greg, while Roger left his family to marry Jane, but the two always found each other whenever they needed to feel something real. If Roger married Joan, he would have had a happier second marriage, and Joan wouldn’t have had to live with a rapist, all in the name of being married.

5 Roger & Jane

Roger got married to Jane, but their relationship failed before it even started. Jane made Roger feel like a free-spirited teenager and so he decided to marry her, despite the opposition from everyone, including his daughter. Jane was also happy to be married to a man that understood her needs, and of course, had the money she wanted.

Too much work meant that Roger became an absentee husband, the last thing Jane could tolerate, and their marriage ended up failing. If Roger had gotten Joan out of his head and concentrated on SCDP and his marriage to Jane, the Roger-Jane marriage maybe would have worked.

4 Pete & Beth

Beth Dawes was one of the best characters in Mad Men that never got sufficient screentime. She was the only woman that managed to bring out some good in Pete. They met while she was dealing with a cheating chauvinistic husband and Pete was also having a hard time with Trudy at home and at work. The affair seemed like a simple one-time mistake at first, but it wasn’t.

Pete was actually in love with Beth and wanted to keep the affair they had going. Beth also needed Pete at the time. The two would have probably saved one another from the hells they were going through if Beth let Pete in, although that would have hurt Trudy immensely.

3 Stan & Peggy

Just when it seemed like Peggy was done making mistakes with men, Stan came along, and she went right back to where she began. Peggy hated Stan at first because she thought he would steal her job, but the two found common ground and learned to get along. It was unlike Peggy to hook up with an egoistic guy like Stan after Pete’s messed her life, but she later saw Stan in a new light.

Their romance was distant, at first, and no one saw it coming until the show ended with Stan giving Peggy a massage as they shared a kiss. The show never gave the viewers the chance to see how the love story ended, but it was great to see Peggy happy for once – it should have lasted longer than it did, though.

2 Don & Rachel

Rachel Menken, the only woman that wouldn’t run away with Don Draper, was also the only woman that didn’t judge Don for cheating on his wife. She was a realist who understood that Don loved his family and that she was only a perfect opportunity he happened to land.

Don also cared for her deeply enough to miss her when they broke up and even got sad when she told him that she was married to Tilden Katz. When Betty and Don divorced, Rachel was the most likely fallback plan for Don. However, the day he dreamed of her is the same day he got news about her death. It was a sad end for the only woman that brought Don Draper back to his senses.

1 Don & Faye

After all that womanizing before his divorce and the tough time getting over Betty, Faye seemed like the perfect person for Don to finally settle with. She was a strong independent woman that Don respected enough to open up to about his messy history and his identity theft.

Faye was also invested in Don emotionally, which is why their relationship deserved a real shot. However, Don went back to his old self and chose Megan over Faye breaking up with her over a phone call. It was one of the saddest breakups that Don ever had and a sad end to the only relationship that Don would have entered without lying.

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