The Sopranos is mostly characterized by crime and violence, but it never hesitates to dive into sentimentalism and romance from time to time. Most of the main characters get paired with a person or two during their time on the series, with mob boss Tony Soprano topping the dating charts thanks to his numerous mistresses.
Even though the existing pairings are satisfactory, it’s hard not to imagine some of the key characters with different people. There are a couple of alternative pairings that make a lot of sense because the characters have similar mannerisms and views or because the circumstances are ideal for them to become an item
Livia Soprano & Junior Soprano
Livia appears in the first 2 seasons as Tony’s overbearing mother before succumbing to a stroke. Junior, on other hand, serves as the DiMeo crime family boss for a brief period before he is forced to take a back seat due to complications from dementia.
Both Junior and Livia harbor a deep hatred for Tony despite being his blood relatives. They even plot to kill him in the first season, a plan that fails. There’s no doubt that by combining their evil minds, the two could grow into a power couple. Moreover, Junior has a reason to woo Livia because he was always envious of her husband Jonny Boy, who also happened to be his brother.
Rosalie Aprile & Bobby Baccala
After her husband’s death. Rosalie tries dating Ralph, as well as a French gigolo but it doesn’t work. Elsewhere, Bobby ends up with Janice, who he is clearly unhappy with.
As two people who know the pain of losing spouses, Rosalie and Bobby can be good together. There are both two of the nicest characters on the show as none of them is ever seen engaging in any form of malevolence. Most importantly, they both understand the mob culture very well, hence they wont clash over anything.
Dr. Melfi & Tony Soprano
Dr. Melfi spends her time in the series behind closed doors as she helps Tony deal with his personal problems. Meanwhile, Tony has an adventurous life as the boss of the DiMeo crime family.
Dr. Melfi is the only person that Tony trusts enough to tell everything. She is also the only person capable of giving Tony a dressing down without any consequences. And she’s never afraid of him, even during moments when he loses his temper. Over the course of the series, the two appear a strong liking for each other too, with Tony always coming back even when he’s gotten better and Melfi continuing to attend to him, even when it becomes dangerous for her to do so.
Carmela Soprano & Furio Gunta
As one of the best mob wives in The Sopranos, Carmela is content with enjoying her husband’s proceeds of crime. As for Furio, he serves Tony diligently after being poached from Sicily but is forced to go on the run after Carmela opens up about her love for him.
Of the couples that ought to have dated, Carmela and Furio come closest to doing so. Though she hesitates, Carmela has a justifiable reason to engage in an affair with Furio because she is aware Tony is a serial cheater. On his part, Furio owes no allegiance to Tony because he hasn’t known him his whole life like the other New Jersey mobsters. Flirting is as far as they go and sadly, Furio’s career gets ruined because of that. It would make more sense for him to flee after engaging in a proper affair with Carmela.
Deborah Ciccerone-Waldrup & Christopher Moltisanti
Working undercover as a socialite named Danielle Ciccolella, Agent Deborah attempts to get information about the New Jersey mob by getting close to Adriana. As for Christopher, he has a great run in the mob before Tony is forced to kill him due to his carelessness.
Christopher appears interested in cheating on Adriana with Deborah at some point. This could have given the undercover FBI agent the opportunity to get close to an actual mobster. A story involving an undercover agent growing to be an influential mob wife or mistress would definitely be an interesting one.
Angie Bonpensiero & Artie Bucco
Big Pussy’s widow, Angie, becomes a successful entrepreneur after her husband’s death. She gets to run a profitable garage and also sets up a shylocking business. As for Artie, he runs the Vesuvio restaurant while maintaining a close relationship with Tony.
Angie and Artie are birds of a feather because of their business acumen. They both understand what it takes to run a successful business hence they’ll always bond over profits and losses. Their association with mobsters doesn’t define who they are either. The two remain focused and keep making their own independent decisions.
Janice Soprano & Phil Leotardo
Tony’s sister Janice has a relationship with thre different mobsters over the course of the series. Interestingly, all of them die. On his part, Phil marshals his New York outfit and engages in a war with New Jersey until he gets killed.
Like her mother, Janice is sadistic and cruel. She is attracted to the men who bear such traits too. That’s why she dates two of the best Sopranos villains, Richie and Ralph. Phil is barbarous too, which makes him the perfect man for Janice. Moreover, as the boss of the Lupertazzi family, he has power, something Janice deeply desires. It’s the reason she tries to influence Richie to pull off a coup de tat against Tony. Her thirst for power coupled with her hatred for Tony makes a pairing with Phil perfect.
Vito Spatafore & Paulie Walnuts
Vito has a great run as a leader of the Aprile crew but is forced to go on the run when details about his sexuality emerge. Paulie, on the other hand, remains part of Tony’s inner circle for most of the series.
Vito’s story is a tragic one as is subjected to one of the saddest Sopranos deaths after other mobsters learn he is a member of the LBGTQ+ community. As for Paulie, he has no relationship arc throughout the series, which feels like a waste, considering how much screen time he gets. He and Vito are both formidable and there are many places and there are many directions an LGBTQ+ storyline between them could go.
Adriana La Cerva & Little Carmine
Adriana starts out as Christopher’s girlfriend but then ends up as an FBI informant before getting killed. Carmine has an easier life as the sign of Lupertazzi crime family founder, Carmine Lupertazzi.
Both Adriana and Carmine enjoy the finer things in life, therefore, they’d have lots of fun together. Carmine is also a nicer version of Christopher. He is eager to get into the movie industry just like the young New Jersey mobsters and is more of a gentleman, something Adriana craves in Christopher but can’t seem to find. A relationship between the two could also help dilute the bad blood between the DiMeo and Lupertazzi crime families.
Tracee & Silvio Dante
Tracee has a stint as a bouncer at the Bada Bing before she is brutally murdered by Ralph. Sylvio, on his part, serves as the DiMeo family’s consigliere until he gets shot by Lupertazzi hitmen.
Both Sylvio and Tracee like the industry they are a part of. As the operations manager of the Bada Bing, Sylvio does his best to ensure everything runs smoothly. He is particularly keen on seeing Tracee succeed since he even goes to her house to get her when she’s late. And since she’s very interested in dating mobsters, a relationship between the two could work.