The Sopranos and Mad Men are often considered two of the greatest TV shows ever made. Though tackling unrelated storylines, both shows are known for their slower pace and solid character development. This isn’t surprising, considering that renowned screenwriter Matt Weiner worked on both projects.
Both shows also delve deeply into the complicated love lives of the characters. Unlike soap operas, no one is the perfect lover. They all keep making mistakes and trying again, and that makes everyone so relatable. If both worlds merged, there are obvious characters that would make a perfect match, but others won’t even be saved by Tony’s therapist.
Would Work: Adriana & Don Draper
A known womanizer, SCDP Creative Director Don Draper always prefers to go after the prettiest of women. When his eye scans through the female characters of The Sopranos, he would quickly settle on Adriana La Cerva. Thanks to her good looks, Adriana has even been the object of admiration for federal agents.
Adriana prefers “bad boys.” Her fiance, Chris, happens to be an unpredictable man and she likes that about him. She’d be more than willing to spend some quality time with Don Draper and maybe even marry him.
Wouldn’t Work: Jennifer Melfi & Roger Sterling
Just as she did with Tony, Melfi is more likely to keep Roger in the patient-zone, rather than see him as a potential romantic partner. She just doesn’t believe in mixing work with pleasure, especially when the men in question are narcissistic womanizers. Roger would surely need professional help from her, though, since he not only has addiction issues, but also chronic conditions, like Tony.
The psychiatrist knows how to rebuff the flirty types, no matter how many pickup lines and favors they throw her way. Roger is just this type of man who would probably try and sleep with her. Unfortunately for him, he’ll have no chance and she’ll turn him down politely and respectfully.
Would Work: Tony Soprano & Joan Holloway
Like Don Draper, Tony always wants the best woman for himself. He is attracted to confident, flirty, and attractive women. Sterling Cooper’s office manager, Joan Holloway, definitely fits the mold. Thanks to her amazing fashion sense and general good looks, she is often admired by both her male colleagues and her clients.
Joan is also attracted to strong, alpha types and Tony proves to be this way for the entirety of the series. She also has no problem dating married men, so the fact that Tony’s wife, Carmela, is in the picture won’t be a problem to her.
Wouldn’t Work: Carmela & Pete Campbell
Pete Campbell is manipulative and untrustworthy. He mistreats his wife, Trudy, throughout the series and goes on to cheat on her a number of times. Despite the fact that he always believes in himself, he has proven to not be as capable in life and his career as he thinks he is.
Carmela would never tolerate Pete’s antics. The major problem she has with Tony is his infidelity, hence it’s unlikely that she’ll tolerate it from a less intimidating man. Given Skyler’s strong personality, she’d have a hard time co-existing with Pete. She wouldn’t even dare do the kind of petty favors Pete asked Trudy to do for him.
Would Work: AJ & Sally Draper
Both AJ and Sally had chaotic journeys from childhood on their way to adulthood. They are both seen as disappointments by their parents, thanks to their laziness and penchant for getting into trouble. Sally starts smoking cigarettes at a young age, while AJ goes as far as to smoke marijuana during his church confirmation.
Sally happens to be very fond of her brother Bobby, while AJ is also very fond of his sister, Meadow. Both of them have also had near-fight experiences with their parents. Once they are both adults, they’d be able to relate to and bond with each other in more ways than one.
Wouldn’t Work: Bobby Baccala & Peggy Olson
Bobby has kids that he loves very much. He requires his romantic partners to love his children and that’s why he was attracted to Janice. Though she was only pretending, she did do a good job of making it seem like she cared about the kids. Peggy, on the other hand, isn’t the biggest fan of children.
When she got pregnant with Pete’s baby, Peggy gave up the baby for adoption because she felt it would be a distraction to her career, not to mention she had a lack of financial or emotional support to raise the baby on her own. Bobby is also a nice person by nature, while Peggy has proven to not be fond of nice guys. The two would definitely not agree on numerous things, leading to their separation.
Would Work: Meadow & Ken Cosgrove
Unlike her brother, Meadow is very focused and hardworking. She is attracted to career men who exhibit similar traits as her own. That’s why she dates Noah (a film school student) and Finn DeTrolio (a dental school student) before getting engaged to Patrick Parisi (a lawyer).
Account Executive Ken Cosgrove would definitely appeal to an adult Meadow. He is not only in the ad world, but also the writing world, having published books. Since Tony wants his daughter to date a good man who isn’t in organized crime, he’d definitely approve of Meadow and Ken’s relationship. After all, the events in the HBO series proved that Tony’s approval is very important.
Wouldn’t Work: Christopher & Trudy
Trudy is a good woman and Chris would definitely be attracted to her because of this. However, she has extremely annoying and controlling parents and this is something Chris would have a problem with. The DiMeo crime family capo doesn’t respond too well to being bossed around.
After becoming a made man, he was supposed to report to Paulie, but he ended up clashing with him on a regular basis. He was also willing to fight off his senior friends and associates when they tried to force him to go to rehab. Chris is guaranteed to have numerous fights with Trudy’s dad, Tom Vogel, leading to him quitting the relationship or maybe even whacking Tom.
Would Work: Silvio & Betty
Betty just wants a strong man who is faithful to her and treats her respectfully. Her marital problems stem from the fact that Don is always cheating and he dismisses her needs and feelings too.
A man like Silvio would be good for her since, unlike his fellow mobsters, he is rarely seen with a mistress. He places more focus on his work as the DiMeo family’s consigliere. Silvio is happily married to his wife, Gabriella, and the two are rarely seen arguing. He and Betty would be a match made in heaven.
Wouldn’t Work: Vito & Sal Romano
Vito and Sal are both Italian-American members of the LGBTQ+ community who are both still in the closet. But, of course, this isn’t reason enough for the two to be a good match.
Sadly, Vito is difficult and unreliable. When he goes into hiding in New Hampshire after being spotted at a gay bar by a Lupertazzi henchman, he finds love in a chef named Jim. A loving Jim even gets him a job, but Vito just wakes up one day and leaves for New Jersey without saying goodbye. He values the mob life rather than his own life and this would be no different if he was with Sal.