The Sopranos

The Sopranos: The 10 Most Questionable Dating Choices

characters on The Sopranos often made bad decisions but these romantic choices are some of the most questionable of the entire series.

If you take out the mafia plot, HBO’s critically acclaimed series The Sopranos easily qualifies as a soap opera. The majority of the other story arcs revolved around love and family. Every character in the show was in a relationship, marriage, or fling. In Tony’s case, he was in all of those, thanks to his inability to stay faithful.

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For a TV show to be near-perfect, the characters need to be flawed. While it was hard to find flaws in the manner in which the key characters conducted their business (Tony never got arrested, for example), their dating lives were characterized by poor decisions. The choices below left viewers gasping in disbelief.

Gloria Trillo Threatened Tony In Order To Keep Him

Tony and his mistress Gloria Trillo kiss inside her apartment in The Sopranos

Gloria was Tony’s most influential mistress. Even after her death, he kept seeing her in his dreams. Tony met her at Dr. Melfi’s office when they were accidentally given the same time slot. He was kind enough to let her take the session after which he went to her workplace and began courting her.

The mobster was fond of Gloria because she was independent. But her dark side soon emerged. She became jealous and controlling. This made Tony back off. Gloria had the option to just dump him when she discovered he had a family. Instead, she began blackmailing him, suggesting he should stay with her or else she’d tell his family. Tony sent his guys to threaten her and warn her to stay away from him. Devastated, Gloria committed suicide.

Vito Left His Lover Without A Goodbye

Vito flirts with Jim in The Sopranos

When two Lupertazzi henchmen saw Vito at a gay bar, he knew his days were numbered. Members of the mob were known to be highly homophobic. Afraid of his life, Vito packed a bag and went on the run. He settled in New Hampshire where he assumed a new identity and tried to forget his former life.

A chef named Jim tried to kiss him but Vito rebuffed him. He later apologized and they began dating. Jim loved Vito very much, even getting him a job as a handyman. Sadly, the mobster grew tired of living a normal life and decided to go back to New Jersey without telling Jim goodbye. Leaving the peaceful life with Jim was a wrong move. Vito got whacked as soon as he returned home.

Christopher Told Tony About Adriana’s Involvement With The FBI

Adriana leaves the Bada Bing with Christopher

Adriana and Christopher started out as an adorable couple. Whenever they argued, they would quickly make up. Christopher also loved her enough to not hook up with other women frequently like other mobsters.

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Unfornutaly, the FBI targeted Adriana, threatened her, and made her an informant. She refrained from giving them any meaningful information. She even let Christopher know what was happening. Instead, he told Tony, who tasked Silvio with eliminating her. As her lover, he should have understood what was happening and tried to protect her.

Janice Pressured Richie To Take Over Power

Janice argues with RIchie about his son's passion for dancing in The Sopranos

Janice and Richie Aprille’s relationship was never a stable one. Both were toxic lovers, though Janice sinned the most. Since she wanted to become the wife of a boss, she began corrupting her husband Richie Aprille’s mind so that he could stage a coup-de-tat against Tony. She even let out the infamous “Oh baby, you’re the boss… it should be you” line in bed.

She was doing this despite the fact that Tony was her brother. Isn’t it better to have a brother who is boss than a husband who is boss? A husband can divorce you. A brother will always be a brother. Anyway, Richie began undermining Tony to the point where the DiMeo crime family boss ordered a hit on him. However, it was Janice who eventually killed Richie after a domestic quarrel.

Bobbi Decided To Kiss And Tell

Junior and Bobbo in The Sopranos

Junior Soprano loved Bobbi a lot. She was the only person who made him smile. Their sex life was great, with Junior making a habit of performing oral sex on her. Since Junior knew that his fellow mobsters had traditional views, he requested Bobbi to never tell anyone about their sex life.

Bobbi did the opposite and began telling everyone about the things Junior did to her. The information reached other mobsters, including Tony, who began mocking Junior. Angry, Junior fired Bobbi and broke up with her. She could have just kept the information to herself.

Carmela Used A.J’s Guidance Counsellor

Carmela cheats on Tony with Robert

When Tony’s affairs piled up, Carmela kicked him out. She then went on a dinner date with A.J’s guidance counselor Robert Wegler. The two kissed in the car but Carmela felt guilty and went to Father Phil for a confession. Despite Phil warning her to stop the affair, she went ahead and slept with Wegler.

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Carmela figured that she could use Wegler to improve A.J’s grades. She also saw him as the perfect tool to use while exacting revenge on her husband. This was selfish of her because Tony would have whacked Wegler if he found out. Luckily, he never did.

Janice Schemed Her Way Into Bobby’s Heart By Scaring His Children

Janice and Bobby argue during a family dinner in The Sopranos.

Janice loved dating mobsters and when Bobby’s wife died, she figured she could take over the wifely duties. She began cooking for him and cleaning his house but he refused to commit.

Frustrated, she began sending his children scary instant messages, pretending to be a ghost. She would refer to things in their room, which she saw from her time in the house. Janice would then play hero by showing up to comfort them. This way, she earned favor with Bobby and he married her. But there was never true love. When Bobby died, she was only interested in the inheritance.

Tony’s Father Never Left Livia

Livia Soprano looking upwards in The Sopranos.

Livia was not a mother, wife, or employer anyone would love to have. She wanted to see her own son dead and couldn’t even coexist well with her caregiver, forcing her to quit. In Season 1’s “Denial, Anger, Acceptance” Tony had a sitdown with Dr. Mefli where he told her that his father Johny Boy Soprano was a tough man but Livia wore him down to the point of depression.

“A guy like that, and my mother wore him down to a little nub,” Tony said. Livia even stopped Johnny from running a club in Nevada. The man who took the job instead of him became a millionaire. Given Livia’s nature, it’s a surprise that Johnny never left him for his own well-being.

Tony Broke Up With Irina Then Assaulted Her Boyfriend

Tony confronts Zellman after he began dating Irina

Irina was seeing Tony at the beginning of the series. She wanted him to commit but he couldn’t because he had a wife. He also didn’t like the fact that she was an exotic dancer, so he ordered her to seek a different career path. He then dumped her unceremoniously.

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In Season 4, Irina began dating Tony’s associate, Assemblyman Ronald Zellman. Tony pretended to not be jealous at first but he couldn’t take it more. He went to Zellman’s house and assaulted him with a belt in front of Irina. Angry, Irina told Carmela about Tony’s affair with her cousin, Svetlana Kirilenko. This led to Carmela leaving Tony.

Furio Fell For The Don’s Wife

Furio and Carmela in The Sopranos

Soon after he came to New Jersey, Furio became Tony’s most ruthless enforcer. Despite his tough persona, he was charming. Most of the people in Tony’s life grew to like him, with Carmela even falling for him.

In Season 4, Carmela and Furio began meeting frequently. To prevent herself from sleeping with him, she would bring A.J. to their meetings. Furio even considered whacking Tony in order to be with Carmela after being advised to do so by a relative. Carmela would later confess her feelings for Furio during an argument with Tony. An angry Tony ordered a hit and Furio was never seen again.

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