Despite having a wife in the incomparable Carmela Soprano, The Sopranos protagonist Tony has had a multitude of extramarital affairs — but which Tony Soprano mistress was the best in the series? More than two decades after The Sopranos first debuted, Tony Soprano remains one of the most memorable characters in TV history. The mob boss who suffered from panic attacks was a unique character concept and made for a more nuanced mafioso than the usual clichés populating crime shows at the time. Beyond his rage, greed, insecurities, and commitment to his family, Tony is also a womanizer. He seldom cares about women for who they are.
However, he ends up with some pretty amazing people, with a few becoming the best female characters on The Sopranos. Over the course of six seasons, Tony had seven mistresses in total and a number of casual affairs. Each Tony Soprano mistress was different, with some seeking to gain from their interactions with the don and others simply out for a good time. There’s no question that the multitude of women Tony Soprano had affairs with deeply affected his marriage to Carmela, who was wholly aware of his dalliances. Regardless, each woman had their own special role in the narrative of the series.
13 Dr. Jennifer Melfi
Though not technically a Tony Soprano mistress, Dr. Melfi’s complex and charged relationship with her patient does at least deserve an honorable mention. The relationship between Tony Soprano and his therapist, Dr. Melfi, is one of the central narrative threads woven through the series. Tony fosters feelings for his therapist pretty early on in The Sopranos, and rather than respect the boundaries of a patient-doctor relationship, Tony makes consistent grasps for more of a romantic connection. Tony repeatedly propositions her, offers her gifts, and flirts with her. At one point when Dr. Melfi shoots him down, he grows incredibly irate.
Later, after Tony and his wife Carmela separate, he tries pursuing Melfi seriously, but (as always) she rebuffs him. At several points, Tony obsesses over this strong intelligent woman to who he feels both attracted and connected. Interestingly, at one point, Melfi confides to someone that she is attracted to Tony’s strength and confidence. However, Dr. Melfi is a professional who would never date a patient, and by the end of the series, she begins to believe Tony is a sociopath, and so she distances herself from him. She’s not one of the women Tony Soprano slept with, but the two shared a connection, albeit a toxic one.
12 Miss Reykjavik
When Tony is at a party with some of his lieutenants in The Sopranos season 4, several Icelandic flight attendants are brought in. One of them, known as Miss Reykjavik, ends up being a Tony Soprano mistress, who later appears in season 4, episode 6, “Everybody Hurts.” Tony and his men inevitably end up sleeping with these women, and in one of the few instances where Tony seems okay with same-sex couples, he watches two of the women make love. While this could have easily been a one-off appearance, Tony is revealed to be sleeping with one of the women much later in the same season, implying this is a semi-regular occurrence.
Identified only as Miss Reykjavik, she has a genuine sense of warmth and connection with Tony, laughing playfully with him as they lie together in bed. Unfortunately, they are interrupted when Tony’s friend Artie calls, crying after having just attempted suicide. A short while later, Tony begins a relationship with Valentina La Paz. She makes brief appearances in a total of three episodes and out of all of Tony Soprano’s girlfriends, his relationship with the mysterious Miss Reykjavik seemed to be the most low-key, and for once caused few waves in Tony’s day-to-day.
11 Annalisa Zucca
This Tony Soprano mistress could’ve spelled real trouble for the mafioso had he actually gone through with full deed. When Tony travels to Italy in The Sopranos season 2 to meet with his Neapolitan associates in the Zucca Crime Family, he learns that the boss, Mauro Zucca, is serving a life sentence. Mauro’s wife Annalisa is the acting boss — something Tony chauvinistically admits he has a hard time accepting. However, it’s worth noting that he has no such hesitation fantasizing about Annalisa while on the phone with Carmela. Despite his biases, Annalisa opens up to him, and for his part, Tony becomes smitten with her.
She takes him to the ancient site of Cumae, where beautiful women, known as Sybils, once gave oracular prophecies. In the Sybils’ cave, Annalisa propositions Tony. He confesses to feeling the same way, but refuses, as she is a business associate. At this point, Annalisa’s cunning plan of seduction turns out to be a no-go, and in annoyance, she forces Tony to lower the price of the cars. Interestingly, it is this emotional and sexual chemistry that leads them to conclude a difficult business deal. While he doesn’t technically hook up with her, the connection between them is so strong that it would be a mistake not to include Annalisa when considering Tony Soprano’s relationships.
10 Charmaine Bucco
The idea that Charmaine was ever a Tony Soprano mistress came as a shock to audiences when the truth came out in The Sopranos season 1. Charmaine Bucco is the wife of Artie Bucco, one of Tony’s oldest friends (and one of his only friends not mixed up in organized crime). By the time the series started, she and Artie had been together for years, and she had nothing but contempt for Tony Soprano and his business affiliates. However, Charmaine reveals that she and Tony had an affair years ago when Tony was dating Carmela.
While there are allusions to her and Tony’s relationship throughout The Sopranos, it’s revealed that the two had a past romance in season 1, episode 3, “Denial, Anger, Acceptance.” In the installment, the Buccos are hired to cater a silent auction fundraiser at the Soprano home, and Carmela ends up treating Charmaine no better than a servant. In a particularly spiteful moment, she tells Carmela this just to inflict pain on her longtime friend after their friendship had reached a crisis point. Charmaine is not a bad person (after all, many of the characters on the show are murderers). However, her vindictive judgmental nature makes her hard to like.
9 Connie DeSapio
Tony Soprano is somehow able to coerce women to bend their morals for a bit of action, as the Tony Soprano mistress Connie DeSapio was a fling that simply shouldn’t have happened, and served little narrative purpose other than to prove that Tony is a ladies man. Connie is a receptionist who works for one of Tony’s main businesses in the waste management industry, and her one appearance is in The Sopranos season 2, episode 11, “House Arrest.” She demonstrates thoughtfulness at her job, something her predecessor lacked.
When Tony comments on her body, he is told she is a born-again Christian who’s not interested in him. Despite this, he later manages to hook up with her, as he has nothing else to do while spending time at a legitimate business. When Tony’s doctor recommends he work on stress management techniques to cope with the strain of office work, the show immediately cuts to Tony and Connie burning off stress together at her desk. His one-off with Connie DeSapio is one of the many things about Tony that haven’t aged well, and she became just a number on the long list of women Tony Soprano had affairs with.
8 Julianna Skiff
The Tony Soprano mistress Julianna Skiff appears a handful of times in The Sopranos season 6 and also fosters a toxic connection with Christopher. Julianna is a realtor who helps Tony sell a piece of property. He initially makes a pass at her, but she declines his advances as she’s engaged and at a good place in her life. However, things between the two come to a head. While signing the paperwork, tension builds between them, and the moment the paperwork is finished, they begin making out, then advance to even more intense activities.
However, Tony stops midway through as he feels guilty when he thinks about Carmela’s devotion to him while taking care of him after he got shot. Later, Julianna attends an AA meeting for help, where she makes a connection with Tony’s cousin, The Sopranos’ Christopher Moltisanti. This proves disastrous for both of them as they enable each other to give in to their worst addictive tendencies, smoking heroin together and spiraling out of control. Tony does continue to pursue her, but she rebuffs him at every turn after his initial rejection. She later pays her respects to Chris at his funeral, where she runs into Tony and Carmela.
7 Lorraine Calluzzo
The Sopranos season 5 saw another rare female mafioso in Lorraine Calluzo, and she’s also a Tony Soprano mistress, however, their affair isn’t chronicled. Lorraine is a loanshark with the Lupertazzi Crime Family who also had a sexual relationship with Little Carmine in the past. When a war begins to rise over issues of succession within the Five Families, Lorraine gets caught up in it. She refuses to make direct payments to Johnny Sack, despite him taking over as head of the family after Carmine Jr. Instead, she sends her payments to Carmine’s son, which greatly insults and disrespects Johnny, ultimately resulting in Phil Leotardo performing a mock execution.
During the negotiations over how to handle the succession issues, Tony reveals he once slept with her. After the mock execution fails to intimidate Calluzo into paying Johnny directly, he sends Joey Peep and Billy after her. Later, she’s executed in her home. While she’s mostly forgettable, her business savvy and gutsy attitude are worth noting. The fact that she’s one of the women Tony Soprano slept with speaks to the oddly incestuous nature of the mafia that The Sopranos presents, as many of Tony’s affairs and relationships happened within the confines of the greater “family.”
6 Valentina La Paz
The Tony Soprano mistress for seasons 4 and 5 was Valentina La Paz, a Cuban-Italian who is also dating Ralph Cifaretto. Tony is first introduced to Valentina by Ralph Cifaretto while they are attending their horse at the stable. Valentina and Tony have a natural chemistry together and end up hooking up despite her also being involved with Ralph. Ultimately, she and Ralph split due to Ralph’s affinity for BDSM, making them incompatible. Things between Valentina and Tony go well for a while, but one of her fake nails falls into his pocket and Carmela finds it while she’s doing the laundry.
When Tony is going through his divorce from Carmela, Valentina is Tony’s primary lover. He tries to imagine Valentina as a wife, but finds it increasingly difficult as time goes on, and he finds himself missing Carmela. One day, Valentina is cooking for Tony and talking about how they should take a vacation and sets her robe on fire. After she sets herself on fire while cooking dinner, she finds herself in the hospital with all of her hair burned off, and the relationship ends when Tony says he’s going back to his wife. Valentina’s response is simply to look at her bald reflection in horror. At least Tony takes care of her medical bills.
5 Irina Peltsin
Introduced as the very first Tony Soprano mistress, Irina is the girlfriend Tony has at the start of The Sopranos and remained his main Goomah for the first two seasons. A Russian immigrant who moved to the US, Irina has dealt with a lot, not least of all Tony’s rages and abusive tendencies. Irina works in a department store, and the two have some wild fights during their dating arc, making audiences question if this affair is really worth it. Eventually, guilt worms its way into Tony’s head and he breaks things off with Irina in season 2.
She became suicidal and Tony tried to get her help, but ultimately ended up having Silvio pay her off to get out of his life for good. By the time she and Tony break things off, it seems he is more concerned about her in an almost paternalistic way. Later, Irina dates one of Tony’s associates, Ronald Zellman. Tony claims he is fine with this, then later attacks Zellman at his own home, violently assaulting the man for his relationship, which leads to Zellman breaking up with Irina. In retaliation, Irina causes further trouble when she outs Tony to Carmela for dating her cousin Svetlana, who was Livia’s caretaker.
4 Adriana La Cerva
Another Tony Soprano mistress that brings the almost incestuous nature of The Sopranos into question is the tryst that never was with Adriana La Cerva. Adriana and Tony never technically hook up, which is the only reason she doesn’t rank higher among Tony’s romantic interests. However, unlike some other women who reject Tony’s advances (such as Dr. Melfi), Adriana and Tony absolutely would have become entangled with one another except they were interrupted — twice. Given their chemistry, it only seems fair to include her. Tony mentions to Dr. Melfi that he’s attracted to Adriana, and despite his misogyny, this is one more shred of proof of his attraction toward intelligent and driven women.
Adriana is Christopher Moltisanti’s lover throughout most of the series. Due to this fact, any tryst she and Tony might have had would have inevitably caused trouble. Rumors are ablaze about a potential affair between Tony and Adriana in The Sopranos after the season 5 installment “Irregular Around The Margins.” The episode saw the two hanging out until 2 am and taking a joyride to go grab cocaine that ended in a car accident. Being together at that time of night and nowhere near their respective homes got the rumor mill churning. Tragically, Adriana is killed after she reveals she has been working as an informant to avoid arrest.
3 Gloria Trillo
Though their relationship was shortlived, this Tony Soprano mistress was probably one of the most influential on the mafioso’s psyche. Gloria is a car saleswoman who sees the same therapist as Tony, Dr. Melfi in The Sopranos season 3. Due to a mix-up, the two meet when they are both scheduled to have appointments at the same time. Tony overhears where she works when she’s talking on the phone, and he goes to Globe Motors under the pretense of buying a car. After they test drive a car together, they go to Tony’s boat, where their relationship starts properly. The pair begin a torrid romance and Gloria falls hard for Tony.
For his part, Tony is immediately influenced by her love of Zen and begins citing Eastern philosophy after their discussions. Gloria begins to show her jealous tendencies, certainly not a trait Tony wants in a Goomah, and her growing rage creates a downward spiral in their dynamic. When Gloria grows jealous of Tony’s wife and threatens him, they have a violent breakup. Tony has his henchmen threaten her life if she does not stay away. Not long after, she commits suicide. Out of all the Tony Soprano girlfriends, Gloria’s fate affects him the most as he continues to dream of her long after her death.
2 Sonya Aragon
Yet another Tony Soprano mistress that The Sopranos uses to “keep it in the family” Sonya Aragon is one of Christopher Moltinsanti’s exes, a woman who strips to pay her way through school. After Christopher’s death and funeral, Tony goes out to Las Vegas in The Sopranos season 6, episode 18, “Kennedy and Heidi,” where he meets Sonya. He informs her of Christopher’s passing, though omits the part about being the one to murder Christopher. They hook up and a little while later, they do buttons of peyote together.
This leads to the two wandering through a casino in an almost shamanistic experience where Tony–a button man (as the mafia call killers)–tries his luck gambling, accompanied by Sonya, who is a companion to him as he confronts the nature of fate while staring at a roulette wheel contemplating Christopher’s death. Sonya is only in one episode, but she is an unforgettable character. She also seeks to represent a less savory facet of Tony’s morality. Not only was he the one to kill Christopher, but then he lied to his ex about it and slept with her.
1 Svetlana Kirilenko
Out of all the women Tony Soprano slept with, Svetlana is the Tony Soprano mistress who caused the most complications in his professional and personal life. Svetlana is a one-legged Russian immigrant and Irina’s first cousin. She is probably the most uncompromising stable woman Tony has ever hooked up with. Despite all she has been through, she is possessed of stoic wry confidence. When Tony comments on this, she explains that while Americans expect nothing bad to happen to them, the rest of the world expects bad things and so are never disappointed. She manages a home care nursing business and acts as caretaker to both Junior and Livia.
At one point in the series, Svetlana gets into an argument with Tony’s sister Janice, who steals Svetlana’s prosthetic leg. Rather than be daunted by someone from an organized crime family taking her legs out from under her, Svetlana just goes to the Russian Mafia for help, cool and resourceful as ever. Irina’s affair with Tony is also revealed to Carmela by Irina after Tony attacks Zellman. This is the straw that breaks the camel’s back, resulting in Tony and Carmela’s separation. Svetlana is pragmatic, confident, competent, and able to see the horrors of the world without being burdened by them.
These Are Far From The Only Romantic Encounters Tony Soprano Had
While there was usually only one Tony Soprano mistress at a time when it came to his main Goomahs, the thirteen listed above are far from the full amount of women Tony Soprano had affairs with over the course of The Sopranos‘ six successful seasons. Excluding Carmela, Tony had romantic excursions with a whopping 17 women on The Sopranos, and a lot of his one-night-stands weren’t given names in the series, while some of them were mentioned rather than shown. A lot of these nameless affairs happened in later seasons of the show, with Tony really ramping up his amorous activities in season 4 and beyond.
Two of the women Tony Soprano slept with were mentioned in The Sopranos season 4, episode 13, “Whitecaps.” In the episode, it’s mentioned that Tony had affairs with a weightlifter and a preschool assistant. There are other affairs that Tony had that were implied in The Sopranos. Season 5, episode 10, “Cold Cuts,” implies that Tony slept with an employee at the dermatology office where he got his cancerous mole removed in a prior installment. Additionally, it’s implied that he sleeps with an unnamed woman in season 6, episode 12. Tony also receives oral sex from two unnamed Bing strippers in season 3, episode 6, and season 6, episode 11.
Tony sleeps with a Plaza escort in season 5, episode 11, and an unnamed young prostitute in season 6, episode 15. The women that Tony almost sleeps with are nearly just as detrimental to his psyche and marriage as his concrete affairs. Over the course of The Sopranos, Tony made it clear how he views women, which is ironic considering his blatant attraction toward women who are intelligent and driven like Dr. Melfi or Adriana. All the Tony Soprano girlfriends are different, but each fling starts with the intention of stroking Tony’s ego. However, none of the affairs seem to end with Tony’s ego fully intact in The Sopranos.