15 Sex And The City Couples Ranked From Worst To Best

Published on September 6, 2016. Updated August 18, 2017

Sex and the City was one of the most successful shows on television during the ’90s and early 2000s. Even though it’s been off the air for over 10 years, it still grows in popularity. The HBO American romantic comedy spun from a novel by Candace Bushnell was on the air from 1998 to 2004 and created mega-stars out of the four leading actresses, Sarah Jessica Parker, Kim Cattrall, Kristin Davis and Cynthia Nixon. As the first of its kind, SATC pushed the boundaries of television by covering racy or controversial topics as it followed the lives of four successful women living in New York City and their various relationships with men while looking for ‘the one.’ Viewers saw a lot of relationships come and go over the course of six seasons so we’ve decided to take a look at all the couples who have come and gone throughout the series and rank them from worst to best. It’s impossible to cover them all, but here are the 15 most popular!

15. Carrie and Berger

After all the bickering played out between these two on-screen, it’s hard to remember how Jack Berger and Carrie fell in love. Carrie met Berger during season 5 after she was reeling from her second break up with Aiden. At first he seemed like just what she needed — he had a great sense of humor, was a writer and their witty banter back and forth was pretty cute. But Berger and Carrie land as the worst couple on this list because they only seemed happy for about a hot second. Once things started getting serious between them, it was one problem after another with these two. First they couldn’t seem to connect in the bedroom; red flags came up when he showed abnormally harsh feelings towards his ex-girlfriend; then Carrie couldn’t get used to sleeping around his sound machine. It was just one thing after another. It all came to a head when Carrie started experiencing success while Jack’s book deal got dropped. He became really whiny and couldn’t seem to be happy for Carrie. All in all, we can’t think of one good reason why these two got together in the first place. We’re sorry, we can’t. Don’t hate us.

14. Miranda and Skipper

Poor Skipper Johnston, he just can’t seem to find happiness. Skipper and Miranda dated on and off during season 1 of SATC. She met him through Carrie and, even though they dated briefly, Miranda never seemed that interested in him. She was more annoyed with him than anything else. It didn’t take long for her to break things off. Skipper is the perfect example of that awkward guy who’s really nice, but there’s just no attraction. Moral of the story: the nice guys never win in the end. Thankfully he moved on from Miranda and began dating someone else, but when he heard from Miranda, he broke up with her at the drop of a hat. Of course, the second go around didn’t work out either. Miranda was simply using him because she saw him with someone else and got nervous that she had made the wrong decision by breaking up with him. This relationship lands as the second worst because it was never going to work out and it was clear Miranda was simply using him.

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13. Carrie and Petrovsky

Carrie and the Russian, aka Aleksandr Petrovsky, met during season 6. It was nice to see Carrie dating someone mature, especially after her relationship with Jack Berger, but Petrovsky was a little too mature for Carrie. He was extremely comfortable and confident in himself and his career, which meant that he wasn’t open to comprising in their relationship. When things started heating up between the two, Carrie felt uncomfortable with his romantic ways. She was extremely critical of his old fashioned courting tactics and when it came time to introduce him to her friends, he didn’t mesh well with her life. He was a good fling to have for a minute, but when it carried on for longer, it seemed extremely forced. It became clear that Carrie just wanted to settle down. Things got even more when Carrie then abandoned her entire life to move to Paris to be with him. Once she got there she quickly realized he wasn’t willing to do the same for her. This entire relationship changed the character of Carrie, as she was beginning to look a little desperate. Thankfully Big came to the rescue and swept her off her feet once and for all.

12. Samantha and Richard

Samantha started dating Richard Wright in season 4 after he hired her to work for him. Although these two seem like the perfect match on paper, Samantha needed a man who was a little more grounded. They were similar in the sense that Richard was extremely confident, successful and liked to play the field. He had a hard time settling down with just one partner. Typically, Samantha would be the same, but she ended up really falling for Richard after they started sleeping together. She knows what she’s getting into when she gets involved with him, but she doesn’t anticipate falling for him. Eventually, Richard feels the same and they both try to commit to a monogamous relationship, but Richard can’t seem to follow through and ends up cheating on Samantha. The entire relationship is dysfunctional as Samantha becomes completely paranoid about him cheating and drives herself crazy. In the end her hunches were right when she catches him in bed with another woman. She ends up heartbroken, but after making him gravel for a while, she ends up getting back together with him in season 5. The second attempt at their relationship is short lived as Samantha realizes she’ll never be able to trust him and ends up breaking things off once and for all.

11. Carrie and Sean

Carrie is starting over after her second break up with Big and begins dating again, slowly. One of her first relationships after Mr. Big is first with a politician and then a twenty-something-year-old bi-sexual named Sean. It’s pretty clear from the get-go that this relationship isn’t meant to be serious or long, he’s just a rebound for Carrie to have fun with after her Big breakup. Even though we know he’s not meant to be the one, he’s definitely not in Carrie’s league and it seems odd that she would date him in the first place. She went from dating an older, successful business man to dating an immature boyish twenty-year-old. The only cool thing about this relationship was when Alanis Morissette makes a guest appearance in the episode and Carrie kisses her during a game of spin the bottle.

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10. Samantha and Maria

This relationship was all wrong from the beginning. Maria basically pushed Samantha into a relationship after they became friends because she developed feelings for Samantha. Maria gave her an ultimatum — they either date or she cannot continue being friends with her. There was also the fact that Samantha doesn’t typically gravitate towards relationships, especially one with a woman! She is constantly proclaiming her love for men so it seemed odd for her to not only hop in bed with a woman, but to become monogamous with one. Although the relationship was surprising, it does help to show just how open Samantha is with her sexuality and that she’s willing to try all avenues. As their relationship continues, Maria becomes increasingly jealous of Sam’s past when they continue to run into men she’s slept with. Maria doesn’t accept Samantha for who she is and constantly judges her for not only the number of men she’s slept with, but the unattached relationships she has with them. On the other hand, Samantha doesn’t seem to truly care about Maria, rather she likes the idea of learning how to please a woman. This relationship ends in disaster (literally, she smashes all of Samantha’s plates) and thankfully doesn’t last long either. Samantha soon becomes bored with the relationship and Maria ultimately can’t get past her jealousy.

Source: E!

9. Samantha and James

Samantha’s relationship with James lasted longer than most expected. She meets James at a Jazz bar near the end of season 1 and the two date into season 2. She takes a page from Charlotte’s book when she prolongs getting intimate with him because she feels as though he is the kind of man she could end up with one day. In the brief moments viewers are able to get to know James outside of the bedroom, he’s incredibly sweet and caring. After falling in love with him, Samantha finally sleeps with him, but it isn’t all it’s cracked up to be. She soon finds out that James is seriously under-endowed. Despite being clearly unhappy, she tries to get past it and even goes to couples counselling, but in the end it was a deal breaker. Funny enough, his name comes up again at the end of season 2 when Samantha meets a man who is so well-endowed she can’t sleep with him. When the ladies are sitting around having cocktails in the season 2 finale episode she announces that she misses James, but thankfully he never makes a comeback.

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8. Charlotte and Trey

When Charlotte met Trey MacDougal in season 3, it was a whirlwind romance. The two began dating after she was nearly run down by his cab in the street. After a few weeks together they got engaged, but it was all wrong considering Charlotte had to manipulate Trey into proposing to her. Trey was perfect on paper, but he was a little moody when it came to his bedroom problems. He was everything Charlotte wanted in a husband. She did her due diligence and took things slow in the bedroom (that was the only part of their relationship that moved slowly). Unfortunately, it wasn’t until the night before their wedding that she found out Trey had difficulties “getting it up.” Charlotte brushed it off as wedding jitters and followed through with their nuptials anyways. From then on their relationship was a constant struggle, beginning with Trey’s mother, to problems in the bedroom and then infertility. These two just couldn’t seem to make it work. Trey wasn’t a bad guy, but the circumstances of their relationship made it impossible to be a good couple.

7. Anthony and Stanford

It took a long time for Anthony, Charlotte’s wedding-planner-turned-best-friend, and Carrie’s bestie, Stanford Blatch, to get together. The women tried to set them up in season 3, but things didn’t exactly work out according to plan. The hot-headed and overly confident Anthony blew Stanford off with one glance. He was extremely superficial and didn’t want to settle for someone like Standford before trying to get to know him. However, down the road Anthony and Stanford got together and by the second Sex and the City movie the two were getting married! In their vows, Anthony said, “It wasn’t love at first sight, but it turns out it was love. You are the first man to accept me for the man that I actually am.” How sweet!

©New Line Cinema/courtesy Everett Collection

6. Miranda and Robert

Dr. Robert Leeds was an absolute catch! He was almost a little bit out of Miranda’s league and somehow it was Miranda who ended up breaking his heart. He bounced back well, but there were definitely some hard feelings afterwards. Miranda met the hunky doctor after a complicated relationship with Steve. Their relationship started in season 6 after Miranda was settled into her role as Brady’s mom, but not quite comfortable with the idea of Steve moving on with someone else. Unfortunately, timing was never really her thing and she didn’t realize she was in love with Steve until she was already knee deep into a relationship with Robert. Robert was the perfect boyfriend. He was great with Brady, successful, handsome and was head over heels for Miranda. He treated her really well. We weren’t all that sad when they broke up because, let’s face it, Miranda was meant to be with Steve, but if Steve wasn’t in the picture, they would have made a great couple in the long run.

5. Carrie and Aiden

Carrie started dating Aiden Shaw in season 3 and he was perfect — too perfect. A lot of fans thought she should have ended up with Aiden because he was everything she wanted in a guy, except for the fact that he wasn’t Big. He was sweet and caring, masculine and successful, but when Big started showing interest in Carrie, she jumped right back into his arms and cheated on Aiden in the process. It was absolutely heartbreaking when they broke up! This was probably one of the most frustrating episodes of the entire series because Carrie was blatantly sabotaging the best relationship she’d ever had with a man. She truly seemed happy when she was with Aiden, aside from when she wasn’t doubting how perfect their relationship was. They ended up giving their relationship another go in season 4 and things seemed like they might work out once and for all. Aiden had forgiven her for cheating on him and Carrie seemed like she was past her whole infatuation with Big. But when Aiden wanted to push their relationship forward she still wasn’t ready. It seemed like she wanted him to be the guy for her, but for some reason he just wasn’t. Regardless, they made a really cute couple and he was so popular with fans that he even made an appearance in the second Sex and the City film!

4. Samantha and Smith

Smith Jerrod was the 28-year-old aspiring actor working as a waiter who Samantha met while out for dinner at a trendy restaurant with the girls. When she first starts sleeping with him she tries to make it fun and light, nothing too serious. However, Smith isn’t just another notch on the bedpost and he is adamant about getting to know Samantha instead of just sleeping with her. When Samantha learns that he’s a struggling actor, she uses her PR skills to turn him into a mega model and movie star. Much to Samantha’s dismay, she starts falling for him. When Smith goes off to film on location, she realizes that she actually misses him. She tries to do all of these things to sabotage the relationship, like telling him to sleep with other women and then telling him to tell people he’s single during interviews. She even cheats on him with Richard! In the end, Smith stays by her side. Ironically it ends up being one of the most stable and healthy relationships she’s been in. These two even had to endure Samantha’s cancer diagnosis in season 6 where he shaves his hair, one of his most valuable assets as a model, to make her feel more comfortable. Their relationship lasts for a long time, even into the first movie four years later. However, to many fans dismay, by the end of the movie, she breaks up with him to focus on herself.

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3. Miranda and Steve

Miranda meets Steve Brady during season 2 at a time when she is most cynical about men. She meets him while she’s at a bar waiting for Carrie. When Carrie doesn’t show up, Miranda goes home with Steve. She initially sees him as just a one night stand, but once he convinces her to give him a shot she really falls for him. Things don’t work out when it becomes clear that Miranda makes more money than Steve and he feels like he doesn’t fit into her lifestyle. Throughout the series they have an on-again-off-again relationship and are able to maintain a friendly relationship even when they aren’t dating. He’s perfect for Miranda, not only because he puts up with her bossy and often judgmental attitude, but because he’s naturally optimistic while she’s inherently cynical. They just seem to work well together and have the basis of a strong friendship underneath their relationship which is the perfect foundation. In season 4 Miranda unexpectedly gets pregnant after sleeping with Steve on one random occasion. This binds them for the rest of the series and eventually, in season 6, they get back together once and for all. The two get married in a very low key wedding ceremony and are the first to start a family. Although these two have their bumps in the road, aside from Carrie and Big, these two have the longest history together and are consistently there for one another.

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2. Carrie and Mr. Big

This relationship was the be all end all for Sex and the City. There was no way the show could end without these two being together. As the series moved forward it became clear that Carrie and Big were meant to be together and that their relationship was something special. She was never able to find anyone that made her feel the way she did with him and she never even came close to being as infatuated with anyone else as she was with him. It’s true their relationship was tumultuous with many ups and downs, but at the end of the day they loved each other and had something that was different than all of her other relationships. She knew at the end of the day, he would always be there for her and that’s what mattered. In the first few seasons it was especially rocky, but they always managed to maintain a friendship, especially after season 3. Finally Mr. Big, John Preston, ends up making his grand gesture to Carrie in the series finale when he goes to Paris to win her over and commit to being in a serious relationship with her once and for all. It took these two a long time to find their way to one another and there was a lot of hurt along the way, but when they finally got together it was the best note to end the series on.

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1. Charlotte and Harry

Charlotte definitely deserved to find her happily ever after, but when she found her prince charming, he wasn’t exactly what she expected! Charlotte is introduced to Harry Goldenblatt in season 5 when she hires him as her divorce lawyer. He pursues her, but she isn’t interested. He’s hairy, bald, sweaty and overall not very physically attractive. However, when she finally sleeps with him she realizes he’s the best she’s ever had. Appearances aren’t everything! After trying to change him, Charlotte learns the important lesson of accepting Harry for who he is because at the end of the day he loves her. Their relationship is adorable and he treats Charlotte like the princess she is. Their relationship has a brief hiccup when Charlotte tries to move too fast with Harry by pushing him to propose, but they find their way back to one another. Charlotte even converts to Judaism for him. Even though these two are faced with the same fertility struggles that tore apart Charlotte and Trey, Harry and Charlotte are able to survive it all and even end up adopting a little Chinese baby.

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