Over the course of Sex and the City’s six seasons, protagonist Carrie Bradshaw had her fair share of eye-opening dates. She learned a lot about love and relationships between the pilot episode and the series finale (even though she ended up with the guy that was always emotionally unavailable, but we’ll let that slide). The boyfriends that she had were sometimes good, sometimes terrible, mostly hilarious, and always fascinating. Some of them still hold a place in our hearts.
Keep reading to see our ranking of Carrie Bradshaw’s most prolific boyfriends and dates. Find out who was absolutely adorable and who was just awful.
10 Totally Awful: Bill Kelley
The worst of Carrie’s boyfriends over the entire series has to be Bill Kelley, the politician that wanted Carrie to do things that made her uncomfortable in the bedroom. Reasons why we hate Bill: he wasn’t understanding of Carrie’s feelings, he had a tantrum when she wouldn’t comply with his wishes, and after everything, he tried to make it seem as if she were the one in the relationship who was inappropriate.
We’re so glad that she used him for inspiration for an article. At least she got something out of their time together!
9 Howie Halberstein
You can’t really call Howie Halberstein a boyfriend. He was more of a bad date that just wouldn’t end. Carrie was set up with him when he came into town for Charlotte and Harry’s wedding, and what could have been a fun fling turned into a nightmare.
As it turned out, Howie had no idea what he was doing and Carrie didn’t correct him. Very high school, as Carrie put it. To make matters worse, he got his knickers in a twist because she didn’t want to spend any more time with him after their bad date.
8 Jack Berger
Carrie spent quite a bit of time with Jack Berger, compared to how much time she spent with some of the other men on this list. But that doesn’t mean he was a good boyfriend. Sure, he could be funny and they had a lot in common. That’s where his good qualities end, though.
The bottom line is Jack Berger couldn’t handle Carrie’s success. We understand it would suck to have your book be a total flop and watch your girlfriend turn into a superstar author, but deal with your emotions in a healthy way. Don’t nearly kill her on your bike and then dump her via post-it.
7 Aleksandr Petrovsky
When Carrie met Aleksandr Petrovsky, he swept her off her feet like she’d always wanted. He showered her with affection the way that Big never did. He came with all the glitz and glamour that she later got angry with Big for not providing after they were married. He even read her poetry and wrote her songs, for goodness’ sake.
If it weren't for the way he slapped her in Paris on their final night together, we definitely would have ranked him higher. We don't hold the workaholic thing against him: he was always straight with her about how important his career was to him. But whether it was an accident or not, the slap wasn't cool.
6 Sean
Sean was one of the better men that Carrie dated, and not just because he was actually Tag from Friends. He was fun, interesting, and different from all her other boyfriends. We’re sure that there would have been something wrong with him eventually, but Carrie didn’t stick around long enough to find out. She was completely uncomfortable with his being bisexual.
What really made Carrie decide that she wasn’t cut out for being with Sean was the party that she attended with his friends. Who knew a game of spin the bottle could be so impactful?
5 Ben
Ben appeared early on in the series, and while we never found out enough about him to judge whether he was serious boyfriend material or not, he seemed like a really decent guy. He was friendly and polite, generous, and down to earth. Carrie might have had a happily ever after with him, had she not messed it up by searching through his personal belongings.
She went rummaging through his property because she was sure that there had to be something freaky about him, and she was determined to find out what that was. Too bad it was Carrie who was actually the freaky one in this situation.
4 Dr. Bradley Meego
Another potential catch that Carrie chose not to pursue was Dr. Bradley Meego, the guy she met when she visited the Hamptons with the girls. As far as boyfriend material criteria goes, the doctor ticked a lot of boxes. Good job? Tick. House in the Hamptons? Tick. Single and interested? Tick. Handsome? Tick.
Unfortunately, Carrie wasn’t in the frame of mind to meet anyone new. While in the Hamptons, Carrie ran into Big and found out that he was back from Paris with a new 20-something girl on his arm.
3 Ray King
We know that Carrie couldn’t have ended up with Ray King. He just had too much energy and an attention span that was far too short. But there’s so much that we loved about him that we wish they could have found a way to make it work.
Ray was talented, interesting, charming, and had intense chemistry with Carrie. He was also attractive and things in the bedroom were 10 out of 10. How often does that all happen at once? If only his mind wasn’t quite so overactive, they could have lived happily ever after.
2 Mr. Big
Mr. Big was never perfect for Carrie, and if his character had been more consistent, he probably wouldn’t have ended up with her. But in the end, he came around and realized that she was important to him and he did want to commit himself fully to her. For that, and his noble trip to rescue her in Paris, we can’t help but rate him highly.
For most of the series, Big is one of Carrie’s worst boyfriends, despite his charm and sense of humor. It’s his actions at the end (no matter how unrealistic they were) that won us over.
1 Adorable: Aidan Shaw
One word comes to mind when we think of Aidan Shaw: adorable. He spent most of his relationship with Carrie doting on her, caring for her, treating her friends well, and being there for her when she needed him. He turned into a bit of an impatient jerk at the end of their time together, but we like to think that’s because she messed him around so much.
Carrie cheated on him, never loved him as much as she loved Big, snapped at him all the time, and only wanted him when she couldn’t have him. If the tables were turned, we’d be calling for his head.
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