5 Of Samantha’s Boyfriends We’d Love To Date (& 5 We Wouldn’t)

Known for her clothes, self-confidence, and sexually liberated attitude, the moments with Samantha Jones’ boyfriends were often the highlights from an episode of Sex and the City. She slept with 35 men (and one woman) throughout the HBO hit series Sex and the City, taking them to bed and breaking their hearts regularly. However, some of these relationships turned into something more, or at least they lasted more than one episode. Some offered hot sex but were emotionally toxic, while others were more chaste but offered security.

Everything changed when she met Smith in season 6 and Samantha finally found someone that she connected with on more than a physical level. It seemed that she finally found the man who allowed her to settle down into a real relationship for the first time since her toxic ending with Richard Wright. She even ended up choosing him over Richard when her former lover returned, and that proved to fans once and for all that Smith was the perfect man to force Samantha to settle down, something no one else could accomplish.

Samantha Jones’s Best Boyfriends

Smith Jerrod

The bashful New York City bartender turned Hollywood sensation was Samantha’s longest-running boyfriend on the series when a determined one-night stand blossomed into something more meaningful. Despite his callow youth and easygoing personality, Smith was more devoted and mature than Sam gave him credit for. Smith was the whole package; with model looks and a killer set of abs, he was also kind, approachable, and never let his fame get to his head.

Samantha almost left Smith when Richard came back into her life, but after dumping Smith and sleeping with Richard again, she felt terrible about her decision. She left Richard’s room and found Smith by the elevator, saying he wanted to make sure she got home okay, which proved to Samantha that he was the perfect man for her. He remained a steadfast companion to Samantha all through her breast cancer battle and recovery, proving he was more than a pretty face looking for the same.

Mr. Cocky

In the Sex and the City episode, “Ex and the City,” Samantha ran out of a Prada store and into a good-looking guy on the street who ended up being christened as Mr. Cocky. He seemed a perfect option for one of Samantha Jones’ boyfriends in season 2. Mr. Cocky gave her his number and said they could meet up for a drink. This led to the bed, and that was when Samantha learned something that makes it even better for her – Mr. Cocky is also well-endowed and warned her ahead of time that others have complained about it.

It seemed too good to be true, but there was just one big problem; he was even too much for Samantha to handle, despite all the various downers she took before their lovemaking. Unfortunately, it had to come between them because he otherwise proved fun-loving and charismatic. They even offered to remain friends, but he never showed up on Sex and the City again after this episode.

Chivon Williams

A successful music mogul who specialized in hip hop, Chivon Williams was an eligible New York City bachelor whom Samantha met and hooked up with in season 3. Unfortunately, his sister Adeena had a problem with her brother dating a white woman. Ultimately, Sam is forced to let Chivon go, even though they had amazing chemistry, and she seemed to be having fun while dating him. Chivon was a great match for Samantha, even if his sister was over-protective and made the entire relationship difficult.

However, there were also a few problems that pulled this relationship down – and none of them had to do with Chivon. Samantha seemed insensitive throughout their relationship, dressing in hip-hop clothing and even implementing some African American culture into her speech. This really showed Adeena’s reason not to want Samantha with her brother. When Samantha said “I don’t see color, I only see conquests,” she proved Chivon deserved better.

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James

Unlike the other men Samantha dated, James seemed to bring out her softer side right from the beginning. After they met at an uptown jazz club, she was swept up by his old-school romantic charm. He wanted to wait to have sex with her so that it would be special. When the big night finally arrived, Sam found out that he might have been worth the wait, but that wasn’t the case sexually. She tried to make their relationship work and even went to a sex therapist with him.

Sam ultimately dumped him over his lack of size which was the opposite of her problems with Mr. Cocky. While Samantha seemed unable to deal with Mr. Cocky, and it caused her to have to back out, this time around, she chose to shame James and dealt with him in a very poor manner. It was one of the worst things that Samantha did to anyone on Sex and the City, and James deserved much better, especially when Samantha kept telling her friends about how small he was.

Maria Diega Reyes

Technically, Maria wasn’t one of Samantha Jones’ boyfriends, but she was one of the longest-lasting partners Samantha had in the series. Arriving in season 4, she helped Sam get more emotionally in touch with herself, even if she didn’t want to admit it. Samantha, who called herself a “try-sexual” on the show, meaning she would try anything, ended up finding more than she expected in her relationship with Maria. Maria was passionate and fiery, yet for all her volatility, she could be surprisingly nurturing and demure.

Inevitably, the fact that she didn’t have a man’s equipment made Samantha break up with her. For a show like Sex and the City, this was one of the more sex-positive moments but that has not aged well when it comes to dealing with LGTBQ+ issues. However, it also resulted in a dysfunctional relationship where Maria wanted to talk about their feelings and Samantha avoided that at all costs.

Samantha Jones’s Worst Boyfriends

Richard Wright

High-powered hotel magnate Richard Wright seemed exactly the sort of man Samantha should be paired with when he showed up in season 4. However, they ended up being so similar that their love life was doomed from the start. Like Samantha, Richard tended to sleep around. Normally, this would never bother Samantha, but she ended up having true feelings for him, and she wanted a monogamous relationship for the first time.

However, Richard wasn’t interested in this. He chose to ignore her feelings of true love, and Richard cheated on Samantha. She ended things to maintain her self-respect. This turned most people against Richard, who they believed broke Samantha’s heart. With this said, Samantha did cheat on Smith when Richard showed back up, but she realized she had made a mistake. Richard never seemed to think he had made a mistake and just said he was as unfamiliar with commitment as Samantha was before she met him.

Adam Ball

In season 3’s “Easy Come, Easy Go,” Samantha took the appropriately named Adam Ball as her lover, who happened to love oral sex. She was happy to oblige until she found out that Adam had “funky tasting spunk,” as she explained to all her friends. She told her friends that no amount of “wheat-grass smoothies” that she fed him to fix the problem had made things any better. Her comments even offended Charlotte, who had to leave the conversation.

To add insult to injury, when Samantha told Adan about her concerns, he felt defensive and believed she was attacking him. His selfishness and immaturity were a clear sign that his semen wasn’t the only thing that was off about him. However, it ended up in a memorable moment where Samantha told him that if he could handle the taste of it, she would too, which created one of the funniest moments on Sex and the City​​​​​​. Adam Ball never showed up on the series again after that.

Harvey Terkell

In “The Caste System,” Harvey Terkell seemed right up Samantha’s alley – he was a wealthy real estate agent who had a penthouse and an actual servant. Sam enjoyed the perks of being the pampered woman of the house, right up until she realized that Harvey’s loyalty was to his maid Sum. Sum was all smiles when Harvey was around, but the moment he left for work, she made it her job to turn Samantha’s stay in Harvey’s apartment into a living nightmare.

He wouldn’t even entertain the notion that Sum could be up to no good and chose her side of the story over Samantha’s. While Samantha loved the money and wealth she could enjoy while with Harvey, the fact that he refused to take her concerns seriously and ignored all her revelations about how Sum treated her means that this is one of Samantha Jones’ boyfriends who didn’t know how to treat the women that he is dating. One might wonder if it is Sum he would rather be with.

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Ed

Samantha didn’t let numbers get in the way of her love life, and to prove that age was nothing but a number, one of Samantha Jones’ boyfriends in season 2 was Ed. A millionaire tycoon who was personal friends with Donald Trump, he offered her everything she could ever want, including diamond jewelry and trips in private jets. Unfortunately, though Ed claimed to have the energy of a man in his 40s, he had the body of a man in his ’70s, and Samantha simply couldn’t overlook it.

While Ed had the money that Samantha often looked for in boyfriends, and he lavished her with presents and gifts, she couldn’t get past the idea that he didn’t look like she wanted from one of her sexual partners. It was funny how the relationship ended, as she felt she had to part ways with Ed before he had a heart attack from taking too much Viagra just to keep up with her.

Dominic

Though Samantha didn’t start dating Dominic until season 2, the girls had known about Dominic for some time. An infamous New York City Lothario, he was an aspiring Richard Wright before Richard’s appearance in season 4. Dominic had already broken Sam’s heart once before, and he had no qualms about toying with her heart again. Samantha told herself she wasn’t going to let him manipulate her so easily again, but Dominic proved too much for her to handle the second time around.

When it comes to all of Samantha Jones’ boyfriends in Sex and the City, there are reasons why people shouldn’t date some of them. Richard cheated on her, and that was bad, but it was also something that Samantha herself did to other people. Other men didn’t match up to what she expected from a boyfriend. However, when it came to Dominic, he seemed to set out to break her heart – and he was the only person to do so more than once when he dumped her the second time for an Icelandic supermodel.