Tony’s Mistresses And Affairs, Ranked Worst To Best

The Sopranos protagonist Tony has had a multitude of extramarital affairs — and the question of which Tony Soprano mistress/girlfriend was the best in the series is still hotly debated. 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.

Tony Soprano mistreats many of his girlfriends throughout The Sopranos. However, he ends up with some pretty amazing people. Throughout six seasons, Tony had seven mistresses and several 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 Tony slept with had a special role in the narrative of The Sopranos.

13 Dr. Jennifer Melfi (Lorraine Bracco)

Tony Soprano’s Personal Therapist

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 and 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, Dr. Melfi shoots him down and 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 whom 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 (Tone Christensen)

The Icelandic Flight Attendant

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 becoming one of Tony Soprano’s mistresses, 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, Tony is revealed to be sleeping with one of the women much later in the same season, implying this is a semi-regular occurrence. Miss Reykjavik 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 very few waves in Tony’s day-to-day life.

11 Annalisa Zucca (Sofia Milos)

The Boss Of The Zucca Crime Family

This mistress could’ve spelled real trouble for the mafioso had he gone through with the 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.

Annalisa’s plan of seduction turns out to be a no-go, and in annoyance, she forces Tony to lower the price of the cars. 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 very strong.

10 Charmaine Bucco (Kathrine Narducci)

The Wife Of One Of Tony’s Oldest Friends, Artie 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 the two had a past romance in season 1, episode 3, “Denial, Anger, Acceptance.” In the episode, 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 reaches 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 (Jennifer Albano)

A Receptionist At One Of Tony Soprano’s Businesses

Tony Soprano is somehow able to coerce women to bend their morals, and Connie DeSapio was a fling that simply shouldn’t have happened, as she served little narrative purpose other than to prove that Tony is a womanizer. 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. Ultimately, Connie became just a number in the long list of women Tony Soprano had affairs with.

8 Julianna Skiff (Julianna Margulies)

A Realtor Who Worked With Tony Soprano

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, and 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 Christopher.

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 continues 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 (Patti D’Arbanville)

A Loan Shark With The Lupertazzi Crime Family

The Sopranos season 5 saw another rare female mafioso in Lorraine Calluzo. However, their affair isn’t chronicled. Lorraine is a loan shark 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, 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 happen within the confines of the greater “family.”

6 Valentina La Paz (Leslie Bega)

Tony’s Main Mistress While Broken Up From Carmela

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 while they are attending their horse at the stable. Valentina and Tony have a natural chemistry together and hook up despite her also being involved with Ralph. Ultimately, she and Ralph split due to Ralph’s affinity for BDSM which she does not share.

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 this incident, 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 was simply to look at her bald reflection in horror. At least Tony takes care of her medical bills.

5 Irina Peltsin (Oksana Lada)

Tony Soprano’s First Mistress On The Show

Irina is the girlfriend Tony had 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 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 (Drea de Matteo)

Christopher’s Long-Time Girlfriend

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 hooked up. 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 if they had not been interrupted — twice.

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 two o’clock in the morning 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 the FBI forced her to become an informant.

3 Gloria Trillo (Annabella Sciorra)

Gloria Also Saw Dr. Melfi, Tony Soprano’s Therapist

Though their relationship was short-lived, this Gloria was probably the mistress who was most influential on Tony’s psyche. Gloria is a car sales agent who sees Dr. Melfi in The Sopranos season 3. Due to a mix-up, the two met when they were 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, Gloria takes her own life. 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 (Sarah Shahi)

Christopher’s Ex-Girlfriend

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 works as a stripper to pay for her schooling. After Christopher’s death and funeral, Tony goes to Las Vegas in The Sopranos season 6, episode 18, “Kennedy and Heidi,” where he meets Sonya. He informs her of Christopher’s death, although he 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 (Alla Kliouka)

Svetlana Is Responsible For Carmela and Tony’s Separation

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 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 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 is never disappointed. She manages a home care nursing business and acts as caretaker to 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, as 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 Tony tended to only keep one mistress at a time, the 13 shown on The Sopranos are far from the only women he had affairs with. Excluding Carmela, Tony had romantic excursions with 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. Many of these nameless affairs happened in later seasons of the show, with Tony 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.

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. He sleeps with a Plaza escort in season 5, episode 11, and an unnamed young sex worker 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.

Throughout The Sopranos, Tony makes it clear how he little he thinks of, which is ironic considering his blatant attraction towards 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.

Did Any Of These Women Measure Up To Carmela?

Not a single one of Tony Soprano’s mistresses held a candle to Carmela. She was the strongest possible match for Tony, someone who would put up with his deficiencies, stand up to his bullying ways, and help keep their family together even when he does everything in his power to destroy himself. However, if there is one person who rivals Carmela when it comes to the women Tony saw on the side: Dr. Melfi.

From the start of the series, Dr. Melfi is one of the most important characters in Tony’s life, even more so than his mafia family. She was the person who tried to help him keep things together and be the person he needed to be. While he was an evil man, it seemed that Dr. Melfi had the ability to make Tony see a better version of himself, which is something even Carmela wasn’t capable of all the time. Also, the one thing that helped Dr. Melfi stand tall above the others is that she rejected Tony in the end, proving her self-worth.

Many of his mistresses were just trysts who didn’t measure up in any way to Carmela or even Dr. Melfi. Women like Miss Reykjavik and Connie DeSapio were mostly flings. Others were from the past and not as important. There were also the mistresses who were disposable in Tony’s eyes, such as Gloria Trillo and Julianna Skiff, along with women who were great pairings for the mafioso but had too many danger signs. Valentina La Paz was another solid girlfriend, but with her tragic end, it wasn’t enough.

In The Sopranos, only one woman was made for Tony Soprano, and that was Carmela. Dr. Melfi was someone who could have been a great for anyone else, but when it came to Tony, he needed someone willing to accept him no matter how many evil things he did. Carmela was that woman.