10 Best Love Interests in ‘Sex and the City,’ Ranked

The four women at the center of Sex and the City were always having dating adventures, from the most romantic to the most atrocious. Although its sequel series, And Just Like That, has not quite hit the mark of the original, Sex and the City is still a fun show that people love to watch and rewatch. There are so many iconic things from the show, like Samantha Jones’ witty innuendos, and the roller-coaster relationships that the women had, as well as the funny dynamic within the group.

Perhaps the most widely-discussed relationship is Carrie and Big, and most fans generally agree that he was a terrible boyfriend to her. Among the four women: Carrie Bradshaw (Sarah Jessica Parker), Samantha Jones (Kim Catrall), Miranda Hobbes (Cynthia Nixon), and Charlotte York (Kristin Davis), they all dated some really great people, and some really awful ones. Some of the more memorable bad dates are Vaughn, who lost it at brunch when his mom didn’t order scallion cream cheese, and Jack Berger, of the horrible insecurities and the infamous post-it note breakup. There are 10 love interests who can be remembered above the rest.

10 Sean

Played by Eddie Cahill

Sean (Eddie Cahill) is probably best remembered for how badly Sex and the City handled his bisexuality, but he was also a really great character and one of Carrie’s better boyfriends. Sean was sweet, warm, funny, and very open with Carrie. From the start, he told her all about his past relationships. Additionally, he adored her. He was always complimenting her and telling her how great and beautiful she was. Sean also introduced Carrie to his friends very early on. He was clearly very proud of her, and of his relationship with her.

The main reason their relationship did not work, was that Carrie was very close-minded about Sean’s sexuality. Additionally, she was uncomfortable with their age gap. As far as Carrie’s one-episode relationships go, though, Sean was one of the better ones. He did not cause any drama, and was just fun and kind and clearly very interested in Carrie.

9 Ben

Played by Ian Kahn

Carrie met Ben (Ian Kahn) at a time when she was wary of dating, and skeptical of the men of New York City. They initially really connected, but agreed to go out on a non-date so as not to risk anything, before soon getting together. Ben was great. He was very funny and genuine, and he valued Carrie. He was a good listener on their date, and he seemed to be interested in pursuing a real relationship with her. Ben even had a Tweety Bird tattoo with a great story behind it.

Eventually, Carrie was so worried that Ben had some dirty secret, that she went snooping around about his things. She was still reeling from many other weird dates and bad relationships, which caused her to become the very thing that she was trying to avoid. Ben walked in on Carrie doing this, which led him to break up with her right away. This was unfortunate for Carrie, but further proof of sound judgment on Ben’s part.

8 Maria Diega Reyes

Played by Sônia Braga

When Samantha Jones first met Maria Diega Reyes (Sônia Braga) at the start of Season 4, the relationship had a lot of potential. They had a strong connection, and Maria really valued Samantha as a person. They had great conversations, and Maria pushed Samantha to open up and try a relationship for the first time since James. They had many great conversations, and they were always making each other laugh. Additionally, Maria appreciated Samantha’s strength after seeing her stand up to Big on Carrie’s behalf.

The show’s writing wasn’t the best when it came to Maria’s character, or to Samantha’s friends’ reactions to this relationship, but Maria was a good girlfriend to Samantha in the beginning. Unfortunately, Maria became controlling and judgmental, and the relationship fell apart. They realized that they wanted different things, had a brutal fight, and eventually ended on more amicable terms. Before that, though, there was a lot of good in their relationship. Maria was one of Samantha’s better love interests, and she really cared about Samantha.

7 Trey MacDougal

Played by Kyle MacLachlan

When Charlotte met Trey MacDougal (Kyle MacLachlan), it started out as the fairytale romance of her dreams. In Season 3, Charlotte was more desperate than ever to get married, and this finally resulted in her trying to get a married friend to set her up with someone. This backfired when the friend showed interest in her, leading Charlotte to run into traffic and nearly get hit by Trey’s limo. It was love at first sight, on the most surface level. Trey and Charlotte had a sweet courtship, and he really did seem to love her.

Unfortunately, once they got married, the problems came to light. There were the bedroom problems first, then the issue of how Trey only saw Charlotte a certain way. Then, once they split up and got back together, things were looking promising, except for the fact that Trey could never put his foot down with his mother, Bunny MacDougal. Then came their struggles to get pregnant, and Trey realizing that he did not want kids. Trey could sometimes be infuriating, like with that truly awful cardboard baby that he gave to Charlotte, but it was understandable why she married him. He was sweet to her and really loved her, and they both really did try to make it work. The relationship may have never been meant to last, but Trey was a good first husband for Charlotte.

6 Jeremy

Played by David Duchovny

Jeremy (David Duchovny) was introduced in Season 6 as Carrie’s high school boyfriend, whom Carrie had broken up with before graduating, in order to see if there were better guys out there. Upon reuniting, they reconnected instantly over dinner. Carrie and Jeremy had a similar sense of humor, and he was very funny. He matched her wit very well, and their history was obvious. He mentioned her book, and he had clearly kept up with what she had been doing. He was kind and thoughtful, and he really cared about Carrie, even decades after they had first dated.

Jeremy then revealed to Carrie that he was currently under residential treatment for his mental health. Carrie was initially a bit insensitive to this, but she came around, and they spent the night together. When Jeremy said that he needed to wait until he was out of treatment in 8–10 months, though, he and Carrie parted ways. Although he was only in one episode, Jeremy was a great love interest for Carrie. He was kind, honest and straightforward, and he clearly really cared about Carrie and valued her. Perhaps he would have made an appearance on The Carrie Diarieshad it not been canceled, but sadly, this was the last that viewers saw of Jeremy.

5 Dr. Robert Leeds

Played by Blair Underwood

Miranda meets Dr. Robert Leeds (Blair Underwood) when he moves into her building in Season 6. They had instant chemistry. They both loved baseball, they got along really well, and they had a natural, easy banter with one another. Even when they barely knew each other, Robert took care of Miranda when she had the chicken pox. Additionally, he asked her out shortly after, and he was always clear about what he wanted. Robert was also a natural with Brady.

The timing of this relationship was unfortunate for Robert, as Miranda had already realized that she was in love with Steve shortly before she met him. She tries to deny her feelings for Steve, but Miranda and Robert eventually break up so that she can get back together with him. Robert may not have been Miranda’s best love interest, but he was a great boyfriend to her, and the two of them were very well-matched. He was sweet, smart, caring, and very mature.

4 Aidan Shaw

Played by John Corbett

Carrie met Aidan Shaw (John Corbett) at his furniture shop, and he was so charming that she bought a chair from him right then and there. This was the start of their first relationship, and it was pretty solid, until Carrie started cheating on him with Big. Until then, they were both very serious about one another. Carrie even gave up smoking for Aidan, and he really loved her. He made an effort to get along with her friends, and he did repairs around her apartment.

Carrie and Aida broke up when he found out about her cheating. They eventually reconciled, but their second relationship was just not the same. Essentially, Carrie was Aidan’s Big, and it was all too apparent the second time around. She pursued him relentlessly, but once she got him back, she was annoyed at him all the time. Aidan was still a great boyfriend the second time around, but his faults became apparent as well. He kept trying to change Carrie, and he was never able to forgive her or trust her again (although who could blame him, especially when she brought Big to his country house?).

3 Smith Jerrod

Played by Jason Lewis

Smith Jerrod (Jason Lewis) was initially introduced as Jerry, an attractive waiter at a terrible raw food restaurant, with whom Samantha had a fling. Samantha and Smith kept seeing each other, though, and she even became his PR representative and helped him make it as an actor through the Absolut Hunk ads. Although Samantha was initially hesitant to open up to Smith and commit to him, they became a great couple. He really and truly loved her, and he was totally committed to Samantha and to their relationship.

Smith was an amazing boyfriend. He was kind and sweet, and he totally doted on Samantha. They got along really well, and they loved to spend time together. In spite of their age gap and external differences, Smith and Samantha really clicked. He was perfect for her, and he never played mind games with her. He just loved her. Smith was totally open and was completely himself, and he supported Samantha when she got sick. He was truly wonderful, and one of the best love interests on the show.

2 Steve Brady

Played by David Eigenberg

As Sex and the City love interests go, Steve Brady (David Eigenberg) was truly one of the greats. From his very first interaction with Miranda, he challenged her, and she in turn challenged him. They were a great couple. Steve definitely had his faults; he was very insecure about Miranda’s success during their first relationship, and he could be very childlike and make Miranda take on all the responsibility. Additionally, there was that terrible but out-of-character cheating plotline in the Sex and the City movie. That being said, though, Steve was a phenomenal love interest, and a great fit for Miranda.

Steve really loved Miranda for who she was, from the start of their first relationship in Season 2, to their reunion and wedding in Season 6. They got along so well that they stayed friends even while they were broken up. Steve was a great dad to Brady, and he was really supportive of Miranda. Steve loved her always, which was apparent when they met up at the restaurant that used to be their spot at the end of Season 3, and he backed her up during her big fight with Carrie. Steve just “got” Miranda, and he was the perfect partner for her.

1 Harry Goldenblatt

Played by Evan Handler

After her perfect-on-paper marriage to Trey fell apart, in reality, Charlotte York grew a lot as a person. She realized that what she had always wanted was not what was right for her, and she ended up opening herself up to newer and better options. Charlotte was not interested in her divorce lawyer, Harry Goldenblatt, at first, when they met in Season 5, Episode 6, “Critical Condition.” However, Harry won Charlotte over with his charm, wit, and utter devotion to her. Initially, Charlotte was hesitant about their relationship, because he was completely different from everything that she thought she wanted. She quickly fell in love with him, though, and the two soon became the greatest relationship on Sex and the City.

Harry was a truly amazing partner for Charlotte. He was smart and loving and honest, and so good to her. He really adored Charlotte, and he made a real effort with her friends. Additionally, Harry was always willing to communicate with Charlotte and to compromise with her. He was mature and thoughtful, and he was also just very funny. He was a great father to Lily and Rose, and the best love interest in Sex and the City.

Sex and the City is available to stream on Netflix in the U.S.

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