SATC: Ranking Samantha’s 15 Love Interests

Sex and the City goes down in history as one of the best television shows of all time. The HBO series aired for six seasons from 1998 to 2004, starring four leading ladies: Kim Cattrall, Sarah Jessica Parker, Kristin Davis and Cynthia Nixon. The show followed four best friends who lived in New York City as they navigated life in their thirties. A huge part of the show centered around their relationships with men, and for Samantha, there was never any shortage of men in her life! While it’s impossible to include them all, we’ve got the most important — here’s a definitive ranking of Samantha’s 15 love interests on Sex and the City!

15. Richard Wright

In a perfect world these two would have worked out, but unfortunately, they were far too similar in all the worst ways. Samantha always seemed very nonchalant and understanding when discussing the topic of cheating with the other women, but once she was in a relationship, she became completely paranoid about it (for good reason). There’s no denying Richard and Samantha had chemistry, but once she caught him cheating on her, she knew she couldn’t trust him and she didn’t want to spend the rest of her life anticipating it would happen again. She was forced to dump him because, although she loved him, she loved herself more.

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14. Dominic

Viewers met Dominic in season 2, but we quickly learned he’d been around much longer than that. He was the first man Samantha ever had feelings for, and we all know that doesn’t happen often! Similarly, he was the first man that ever broke her heart, so when she ran into him again, she was determined to do to him what he did to her. Unfortunately, her plan backfired because, even though she went into it with the intent of breaking his heart, he beat her to the punch…again. We’re pretty sure she learned her lesson, but he remains the second worst love interest for her!

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13. “We” William

William was the perfect example of a man who knew how to sweet talk a woman. He would tell Samantha everything she wanted to hear, but at the end of the day, he was all talk, no action. He won her over by using the phrase “we” when talking to her and making her believe they were going to spend the summer together in the Hamptons. She found out the hard way that he’d just been saying all those things so that he could sleep with her after he stood her up at a restaurant.

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12. Harvey Terkel

Mr. Harvey was a real estate investor who’d made it big after he’d turned Chelsea sweatshops into luxury co-ops, but what’s strange about him was that he had an actual “servant” named Sum who lived in his home. Samantha was okay with it at first, until she realized that his servant was in love with him, but conveniently only seemed to show her true colors when Harvey wasn’t looking. Harvey thought she was the sweetest lady in the whole world, but once he left the house, Sum would kick Samantha out of bed and call her names. Then one day when Samantha stood up to her, Sum pretended Samantha hit her! Harvey ended up believing Sum over Samantha which was a definite deal breaker.

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11. Brad the Taxi Thief

These two got off to the wrong start when Brad stole Samantha’s taxi right from under her nose. Unbeknownst to him, he stole from the wrong lady because Samantha was not about to let him get away with it! She hopped in the taxi right beside him. They ended up having a brief fling, but just as he was a jerk on the streets of Manhattan, he was also a jerk in the bedroom when he told Samantha she was due for a wax!

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10. Warren the Baby Talker

Samantha is open to a lot of things in the bedroom, but baby talk is not one of them. In season 4 she headed out for a night on the town wearing fake nipples as a little experiment to see if it attracted men. Unfortunately, all she attracted was a man-child named Warren who started talking to her like a baby once they hopped into bed. Safe to say, Samantha was not into it.

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9. Chivon Williams

In season 3 Samatha began dating a record executive named Chivon Williams. Samantha assumed that if race wasn’t an issue with her, it wouldn’t be an issue with anyone else. She was sadly mistaken! Chivon seemed like he was really, really into Samantha, but his sister’s opinion meant more to him than his own, and she did not like the idea of her only brother dating a white woman. Despite all of this, we’re guessing that even if Chivon’s sister liked her, it probably wouldn’t have lasted because, even though they had chemistry, they didn’t  have a lot in common. As hard as she tried, Samantha didn’t fit into his world.

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8. Garth

When Carrie went through her bad break-up with Aiden in season 3, she invited all the women to go to L.A. with her. A small Hollywood production company showed interest in making her columns into a movie, so even though she wasn’t too keen on the idea, she saw it as a much-needed free vacation. While in L.A., Samantha met a male model who worked in the adult entertainment industry. While Garth ended up being a very emotional and sentimental person, their relationship never would have worked because not only was that not what Samantha was looking for, but she was more attracted to his career (and body) than his personality.

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7. Don from the Sports Bar

In relationships, Samantha expects sex to trump everything, but this wasn’t the case with Don. She met him during season two when the ladies moved their weekend pick-up game to a sports bar so they could increase their odds of meeting men. It didn’t take long for Samantha to find Don and she lured him in by pretending to be interested in sports, but he wasn’t the right guy for her because she quickly learned that she only scored in the bedroom if Don’s New York teams scored in the game. When his team went through a losing streak, she’d had enough of this relationship.

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6. James

Poor James. The relationship between these two went on a lot longer than we expected, especially since Samantha was so unsatisfied with him in the bedroom. She constantly complained about his inadequacies in the bedroom, but she stuck with the relationship because she loved him and truly thought he was a good man. Samantha even went to counselling with him when he began to realize she wasn’t happy! This is not the Samantha we got to know later on in the series. They dated briefly at the beginning of season 1 and even got back together at one point, but at the end of the day, he couldn’t give her what she needed.

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5. Dr. Mark Raskin

This relationship was hot and heavy but didn’t really venture outside of the bedroom. We only got to meet Dr. Mark Raskin in one episode during season 3, but he managed to hold Samantha’s interest for more than one date. It might’ve had something to do with the fact that he introduced her to a little magic pill. Sadly, he had to dump her because she began getting obsessed and slightly addicted to their drug-fueled escapades!

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4. Maria

When Samantha started dating Maria in season 4 it took us all by surprise. She definitely wasn’t a fan favorite because, while Samantha enjoyed their relationship at first, it quickly became clear that the two were extremely different in many ways. Maria kept trying to change Samantha into something that she wasn’t, and was jealous of her extensive past with men. She didn’t seem to accept the fact that Samantha was not a lesbian, but rather bisexual (or simply experimenting). We put them higher up on the list simply because Maria wasn’t a bad person or partner, it was just that they weren’t exactly the perfect pair.

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3. Ricky the Fireman

Ricky was just the sweetest man ever, plus, he’s a firefighter which is pretty hot! Samantha met Ricky in season 3 when she and the girls took a ferry to Staten Island so that Carrie could judge the New York Fire Department’s annual male calendar. Samantha and Ricky hit it off right away, but their relationship didn’t really go past physical appearances. They were definitely attracted to each other but didn’t have much to talk about. She basically dated him so that she could live out her fantasy which later backfired when she was left butt-naked in the fire station after her man rushed off to put out an actual fire!

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2. Jeff Fenton

Many people will be surprised to see Jeff Fenton so high up on this list because not only was his relationship with Samantha short-lived (pun intended), he wasn’t exactly her type. When she first met him in a bar, they hit it off right away. He was extremely witty, intelligent, and successful. Not many men can return Samantha’s banter right back to her, but Jeff could! Unfortunately, when he got up off the stool she’d realized she just agreed to go on a date with a very, very short man. While their chemistry was good, and he was able to keep her satisfied in the bedroom, she couldn’t get over the fact that he was so short. They dated for a little while but eventually broke up for good.

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1. Smith Jared

These two were hands down one of the best couples within the entire series! Fans were truly heartbroken when in the spin-off movies they broke up — especially after everything they’d been through! She’d finally found a man that could give her everything that she needed, inside the bedroom and out. To top it all off, he loved her unconditionally. He stuck with her as she battled cancer and even when she cheated on him. He seemed to understand her better than she even understood herself. These two were perfect for one another, if there was any hope for a third movie, we would hope they would get back together!