Almost 30 years after the series aired, I’m deciding to rank the love interests of the four girls from Sex and the City. The show centered around love, sex and dating and showcased good, bad and diabolical men. Although there have been two movie sequels and a spin-off series, I’m only focusing on the men featured in the original show and none of their actions past the finale.
11. Jack Berger
To attain last place on this list, you have to be exceptionally villainous; unluckily for Carrie, Jack Berger was. Berger’s defining quality was his insecurity, which made Carrie’s problem in every scene they shared. Carrie and Berger met because of their shared editor; he initially comes across as very similar to Carrie in their mutual passion for writing and quick wit. Quickly, you realize that his self-deprecating humor isn’t sarcasm, but rather a reflection of his low self-esteem. He and Carrie fought in almost every episode over juvenile things such as her singular minor criticism of his book and her dislike for parsley. His constant judgment of both her and himself made him insufferable. He was incapable of feeling happy for her unless he was succeeding, which is arguably the most toxic trait a man can have. The best thing he ever did was break up with her (even though he did it via sticky note).
Best Moments: “He’s Just Not That Into You” advice to Miranda and banter with Carrie
Worst Moments: Abandoning Carrie at Samantha’s red carpet event for Smith, his inability to take constructive criticism from Carrie about his new book and the post-it note
10. Steve Brady
Steve was the epitome of a man-child with a level of insecurity comparable to Berger. I started off the show loving Miranda; I lost a little bit more respect for her each time she chose to stay with Steve. Steve’s lack of ambition or responsibility contrasted with Miranda’s core qualities; the two had nothing in common, and sure, opposites attract, but they were way too different. Despite lacking any drive, he was always jealous of Miranda’s career success, even refusing to attend a work event for her because he didn’t want to dress nicely or wear a suit that she had bought him. He doesn’t think things through and is a mediocre father at best. Early on in their relationship, he asks Miranda to have a baby with him. When she says she’ll end up being the only one to take care of it, he tries to prove her wrong by getting a dog as a sort of “practice run”. He doesn’t take care of it at all, and for whatever reason, the usually rational Miranda proceeds to have a baby with him in the later seasons. Also, the way he said Miranda’s name was incredibly annoying.
Best Moments: Making Miranda laugh and his commitment to Miranda
Worst Moments: Not taking care of the dog, refusing to watch Brady alone when Miranda wanted to go on her girls’ trip to Atlantic City and punishing Miranda for her success/the suit debacle
9. Mr. Big
Mr. Big was suave, successful and witty. While he and Carrie had consistently great chemistry, his constant fear of commitment to her is the main reason he is so low on this list. While he refuses to commit to Carrie, he almost immediately marries his second wife, Natasha, after his and Carrie’s season one breakup. He proceeds to cheat on Natasha with Carrie, effectively making her the other woman. Most of their relationship consisted of them dating, him leaving, then returning the second she is happy with someone else to ruin her relationship. He was always embarrassed by Carrie; he refused to take her to places where he risked running into people he knew (which he never did with Natasha) and was always reluctant to introduce her to his friends.
Best Moments: Chasing her down in Paris, offering her the money she needed during her financial troubles despite them being exes and showing up to her book signing to apologize for the way he treated her
Worst Moments: Cheating on Natasha with Carrie, moving to Paris without consulting Carrie, checking out other women in front of her and refusing to show her off to any of his friends
8. Richard Wright
Initially, Richard seemed like the perfect match for Samantha; they were both witty, fun-loving, career-focused and loved sex. While most other men that Samantha had dated wanted her to commit, which drove her away, Richard was even more avoidant than she was, which is likely the reason that she wanted to commit to him. His charming and smooth persona made him incredibly likable at first; however, he fell out of my favor when he cheated on her. Although they briefly reconcile, their trip to Atlantic City with the rest of the girls reveals that his betrayal weighed on Samantha too much for her to continue with the relationship, and they break up in that episode.
Best Moments: His vulnerability with Samantha, his ability to bring out her softer side, flying Samantha and all of her friends out to Atlantic City
Worst Moments: Not picking out the gifts he gives Samantha, cheating on her and his control issues
7. Skipper Johnston
There’s not much you can say about Skipper; he was introduced in the first season as Carrie’s friend who pursues Miranda. Skipper was always kind and authentic, but a little boring. He was kind of like Steve, and when Miranda ultimately leaves him for Steve, it gives the impression that she has a type. Despite his sweetness, he often came across as clingy, which was a huge turn-off for the fiercely independent Miranda.
Best Moments: All of the times he is honest and vulnerable with Miranda and his willingness to commit to her
Worst Moments: Pressuring Miranda to be more serious with him and his disappearance after season two
6. Aiden Shaw
Aiden was the next man Carrie dated after her first break-up with Big. He was sort of the antithesis of Mr. Big. He wasn’t some suave Wall Street guy just looking to have fun. He was a down-to-earth carpenter who always wanted to be serious with Carrie. He treated Carrie much better than most of her exes did, despite her cheating on him with Mr. Big very quickly into their relationship. They break up because of this, but rekindle their romance in season four. The two even became engaged, but Carrie was never truly invested in their relationship, at least not as much as he was. Although he was overall a good boyfriend to Carrie, he consistently ignored her feelings and tried to change her.
Best Moments: Forgiving Carrie for her infidelity, buying Carrie her apartment,and doing construction to open up space for the two of them
Worst Moments: Trust issues after she cheated, asking her to get rid of her clothes and refusing to accept her for who she actually was
5. Aleksandr Petrovsky
This may be controversial, but Aleksandr was one of my favorite love interests on the show. He was an artist and a romantic who loved and accepted Carrie despite her flaws. He wrote her poems and songs, treated her to romantic date nights, jewelry and clothes, and, unlike Mr. Big, invited her to move with him to Paris. He was proud to be with Carrie; he introduced her to his friends quickly and always treated her like she was the prize. Many of Carrie’s friends disliked him because they found him pretentious; however, he never acted like he was above any of them and made an effort to get to know the group. Once they move to Paris, the relationship starts to go downhill. He prioritizes his work over her and ignores the fact that she feels isolated after their move. When Carrie finds French fans who want to throw her a party, he guilts her into skipping it so she can support him through his anxiety during his showcase. He ignores her while they’re there, and the two fight when they arrive home. During the fight, he accidentally hits Carrie because of muscle spasms caused by his anxiety. Although he apologizes, Carrie storms out and ends up reuniting with Big, who, as a romantic gesture of sorts, attempts to “teach him a lesson”. While the incident wasn’t intentional, it understandably turned a lot of fans off from his character.
Best Moments: “The Carrie necklace”, defending Carrie’s article to his friends and the romantic date to the Opera
Worth Moments: Persuading her to abandon her “Carrie Bradshaw Party,” neglecting her in Paris and their fight in the finale
4. Trey MacDougal
Trey was Charlotte’s first husband. He was always a gentleman and was eager to marry her, always acknowledging her worth. While Trey may have seemed bland and had “intimacy issues,” he was always good to Charlotte, and when compared to all the other men on this list, he was a breath of fresh air. While he could be emotionally distant at times, Trey’s biggest fault was his much too close relationship with his mother, who constantly picked fights with Charlotte. They ultimately divorced over him not wanting children; however, even if they were on the same page about kids, they likely wouldn’t have lasted due to the frequent conflicts between Charlotte and Mrs. Macdougal.
Best Moments: Proposing to Charlotte outside of Tiffany’s and going against his mother to give Charlotte their apartment in the divorce
Worst Moments: The cardboard baby and every time he showcased his inability to set boundaries with his mother
3. Harry Goldenblatt
Charlotte had arguably the best taste in men due to her high standards. Harry was Charlotte’s divorce lawyer and the exact opposite of who Charlotte imagined she’d be with; he was goofy, out of shape and had hair everywhere but his head. However, Harry charmed Charlotte with his kindness and skills in bed. He always treated Charlotte as the prize and truly loved her. He, unlike Trey, was just as eager as Charlotte to be a parent and was supportive of Charlotte throughout her fertility struggles. He wasn’t without his faults. The two did briefly break up after he got mad at Charlotte for not letting him watch a baseball game during the dinner she had prepared to show her dedication to Judaism after converting for him. In the argument, Charlotte implies that she’s out of his league, which upsets him, as he knew everyone else thought she was, but he never thought Charlotte did. Ultimately, the two work things out and get married and finish the show with the strongest relationship throughout the entire series.
Best Moments: Him confessing his love for Charlotte, changing his messy habits to please her and his proposal
Worst Moments: Their break-up and forcing her conversion to Judaism
2. Dr. Robert Leeds
The fact that Miranda ends up with Steve and not Robert physically pains me. He seemed like Miranda’s perfect match. The two are neighbors whose friendship quickly turns romantic. Robert is kind, charming and smart. He is supportive of Miranda and not intimidated by her success; he helped out with Brady (Miranda’s son from Steve) and was emotionally available. While their relationship did move somewhat fast, it was very healthy, especially compared to her previous ones. They unfortunately broke up because of Miranda’s lingering feelings for Steve; her decision to leave him is likely the biggest fumble in all of TV history.
Best Moments: The “I love you Chocolates,” interactions with Brady and inviting Miranda to the game
Worst Moments: None.
1. Jerry ‘Smith’ Jerrod
Smith is one of Samantha’s only long-term relationships throughout the show; their relationship starts off as purely sexual until both catch feelings for one another. Samantha becomes Smith’s publicist and helps him get his career off the ground. Shortly after they officially get together, Samantha is diagnosed with breast cancer, and he is incredibly supportive and remains loyal to her despite her lack of sex drive as a result of chemotherapy. At his first big red carpet event, he shaves his head to make Samantha feel better about losing her hair, which is, in my opinion, the most romantic gesture shown in the series. He was sweet, charismatic and intoxicatingly attractive, which earned him the number one spot on this list.
Best Moments: Shaving his head for Samantha, his public declaration of love for her in an interview and helping Samantha work through her fears of commitment.
Worst Moments: Also none, he was perfect.