Mad Men gets great mileage out of the subplots involving romantic couplings that should and (mostly) should not be happening. Don Draper, being the show’s centerpiece and a privileged man of means, has more than his fair share of dalliances. The results are almost never pleasant. His affairs ultimately lead to the breakdown of his marriage, awkward situations at the office, and a growing disgust with himself over his hedonistic lifestyle.
While his actions are often the catalyst for unhealthy relationships with women, they do make for good drama. It also opens up the debate over who is the best person for Don and who he should never have touched with a ten-foot pole. Here are Don’s Major Love Interests, Ranked.
10 Aimee Swenson
Aimee does not get much time in the grand scheme, yet she is an important figure in Don’s life. In a way, she is responsible for opening him up to a world of free sex. She is a prostitute at the brothel run by his stepmother, Abigail.
One night, Aimee sneaks into an adolescent Don’s room and takes his virginity. The act would fall under statutory rape — not good, not good at all. His memories of his first time stay with him and make up an important storyline late in the series’ run.
9 Bobbie Barrett
Don’s most destructive relationship is with Bobbie Barrett. She is married to Jimmy Barrett, a comedian who Don must keep in line to save the Utz chips account, and manages his career. She also has two adult children. Bobbie is far from the ideal person to be romantically involved with. Even worse, she sought him out based on a recommendation from a friend, as if he were a gigolo.
Upon discovering this information, he cuts off their relationship, but Jimmy finds out and tells Don’s wife, Betty. That marked the beginning of the end for Don and Betty.
8 Sylvia Rosen
Despite settling into what appears to be a happy second marriage with Megan Calvet (more on her later), Don steps back into his old habits soon enough. He engages in an affair with a neighbor’s wife, Sylvia Rosen. Sylvia is also a close friend of Megan’s. Neither spouse discovers what happens between the two, but his daughter, Sally, walks in on them. He rushes after Sally and that is the end of their affair.
Sally’s attitude towards her father, however, changes significantly after this event. She does not respect him as much as she did before and hates him for having to hide his indiscretion.
Calling Allison, Don’s secretary, a major love interest is a stretch, but she is important in explaining Don’s destructive side. Where his affair with Bobbie Barrett was more self-destructive, as her husband had been cuckolded many times before, his one-night stand with Allison hurts her more than it does him.
He takes advantage of her kindness and sleeps with her. The next day, she has wrapped his Christmas gifts for his family, and he hands her $100 to repay her. The money does not send the right message. She goes from seeing him as a possible romance to being crushed and leaving the firm. Nice work, Don.
6 Midge Daniels
Midge is the first woman in Don’s life the audience gets to see. She is an artist living in Greenwich Village and true to the stereotype, she is a beatnik, a precursor to a hippie. He visits her often when he is in the city and the affair never reaches Betty.
Regardless, the show makes it abundantly clear that Midge is not right for Don. She smokes weed, is in love with another man and, as we see in a later encounter between the two, willing to sell her body in order to satiate a drug habit.
5 Rachel Menken
Rachel comes into Don’s life when it feels like it is unraveling for him. His wife is unhappy and seeing a therapist, and his affair with Midge Daniels does not satisfy him, not to mention the toxic environment at the office.
After treating her in an obnoxious, sexist fashion during their first business meeting, the two hit it off and start seeing each other. She is a strong and capable woman who wants to restore her family’s business to its past glory. Don never truly sees her. He wants her as an escape, a way out of his empty life, and she rightly refuses him.
4 Megan Calvet
Megan’s relationship with Don fails to last in a healthy fashion beyond the initial honeymoon phase. She wants something out of the marriage beyond mutual love and respect, namely a career in front of the screen, and he is unable to care for his wife in the way a husband should.
The moment she starts her career is the moment he starts sleeping around. That means he was not interested in Megan the person as he was in her looks and in a superficial attachment to her. He eventually hands her a massive divorce settlement, which she claims ruins her chances of being taken seriously as an actress.
3 Suzanne Ferrell
A massive red flag, aside from infidelity, surrounds Don’s relationship with Suzanne. She is Sally’s elementary school teacher. That has the makings of a huge neighborhood scandal, the kind where all involved parties would leave for places where no one knew who they were.
That said, Suzanne seems to be good for Don in ways other women are not. Her idealistic streak attracts him, provides him with a healthy reprieve from the materialistic pessimism he sees in the advertising industry. She also genuinely cares about him, to the point where she asks how he is doing when he calls off their affair. Don finds the statement so unusual that he compliments her on it.
2 Faye Miller
Dr. Faye Miller enters the picture as a consumer research consultant hired by Sterling Cooper Draper Pryce to help improve their sales. She is a confident and capable woman, who is also able to keep the secret of Don’s true identity, something even Betty is incapable of doing.
Their relationship is steamy and pleasant. She understands him, the good parts and after he rebuffs her for Megan, the bad parts. Her warning to Megan about Don’s ability to lose interest quickly proves to be prophetic.
1 Betty Draper
Don’s first wife, Betty, remains his strongest romantic partner. She gave him over 10 years of her life and three children. Though his womanizing, distant attitude, and his secrets, along with her interest in Henry Francis, ultimately lead to divorce, Betty knows Don better than anyone. Distance later allows her to see what makes him tick.
Also, as the flashbacks show, no one had ever made him happier or feel better about himself at the start. It is one of the few times the audience sees him in an idealistic mode. Too bad he ruined it.