Much of Carrie Bradshaw's dating history reads like a rap sheet—lots of regrettable mistakes, failed romances, one-night stands, and obvious red flags that everyone but she could see. But there were also the big loves. Carrie's long-term, life-changing relationships with Mr. Big and Aidan are among the most iconic in TV history.
When I revisited Sex and the City most recently, I was surprised to discover Carrie Bradshaw didn't date nearly as many men as I'd thought. There were 28 guys she went out with and/or slept with, not including men she maybe just kissed once or men she may have referenced dating when talking but that we never actually met during the series. Among these 28, there were a few jerks and weirdos, several just-for-fun flings, a handful of innocent casualties who really did nothing wrong except get caught up in the chaos of Hurricane Carrie,and then, of course, the main players who logged the most screen time and experienced the full roller coaster ride. Scroll down for a refresher on the many men Carrie Bradshaw dated, ranked from worst to best.
It's hard to say which of the guys Carrie dated was the worst of all—there were so many bad ones—but
Vince Vaughn Keith Travers proved himself especially despicable when he lied to Carrie about his connections and being Matt Damon's agent and looking for a fancy new mansion to replace his already super fancy mansion. Her Los Angeles fairytale was quickly dashed when she woke up to Carrie Fisher barking at her hunky Hollywood impostor to no bring hookers over when he's house-sitting. Ouch.
A recovering alcoholic, Patrick Casey started dating Carrie and swiftly fell off the proverbial wagon. His new substance of choice? Carrie Bradshaw. After four dates he told her he loved her, then took offense at her suggestions to the contrary. When she decided they ought to pump the brakes a bit, if for no other reason than the sake of his sobriety, he went into a full downward spiral. When a guy shows up drunk and screaming profanities on your street in the middle of the night, that's probably your cue to end things. The only reason Patrick Casey isn't listed as the worst guy of all is because Carrie did kind of push him into dating before he was ready.
This guy had a bad attitude with a capital B-A-D. After essentially being forced into a set-up with Howie Halberstein, a friend of Harry Goldenblatt's, Carrie endured a painfully unpleasant (literally) sexual encounter that she described as very high school—as in, he had no idea what he was doing and she said nothing. When she politely declined an invitation to round two during Charlotte and Harry's wedding, he proceeded to use his best man speech as a platform to call out Carrie for rejecting him. So not cool.
The worst in a trio of "freaks" Carrie went through in the beginning of Season 2, she dubbed this guy "The Man with Two Faces." He was sweet and funny with her, but then suddenly snapped at the people standing behind them for no good reason. That kind of unpredictable aggression is a big fat red flag. Run away, Carrie, run far away.
PJ was another one of Carrie's freaks. He was an independent film producer who had just received acclaim for his documentary on seagulls. Except he didn't care one bit about the seagulls—they were just his stepping stone to fame and success in the corporate movie world. But... what about the seagulls??
The final of the three freaks was "The Man Who Steals Cheap Used Books for No Reason." So he shoved a book down his pants—there are worse things a guy could do. That said, it's still probably a good thing she didn't pursue things further with this sticky-fingered fellow.
When Carrie was studying women who date like men in the first episode, she turned to Kurt Harrington. He's basically just sex organs on legs, with little desire for anything beyond that level of interaction. Carrie tries to play him at his own game, but it doesn't quite have the effect she was hoping for. The silver lining in all this is she first meets Mr. Big—she runs into him on the street and drops her purse full of condoms—after sleeping with Kurt.
Willie Applegate was a graphic designer Carrie went on a late-afternoon semi-date with, solely as a way to alleviate the pressure she felt about her upcoming first date with Jack Berger. This poor guy... he was so awkward and nervous. He asked if she was staring at his stye, then got balsamic vinegar in his stye, a pigeon landed on his head and he fell out of his chair. It was a disaster, which of course made Carrie feel much more at ease about things with Berger.
Why Carrie didn't learn sooner that she doesn't do well dating younger guys is a mystery to me. Wade Adams worked at a comic book store and lived with his parents, but his real shining moment was when he threw Carrie under the bus and blamed her for bringing marijuana into the house. Carrie's shining moment was when she promptly exited the house with said marijuana in hand.
Jake wasn't so bad, but he wasn't so great either. Carrie was feeling down on herself after that very unflattering New York Magazine cover came out, and Jake, being the insensitive dude that he was, failed to recognize how teasing her for it might not be very nice. Carrie didn't end up going home with him though, so good for her.
So he may have mistakenly thought Carrie was a high-class escort and left an envelope of cash by the bed after their time together—but they had fun and, to be fair, Carrie's friend who introduced them was a high-class escort. Let's chalk it up to an innocent misunderstanding.
There's an unwritten rule in dating: don't try to turn your f*ck buddy into your boyfriend. To be clear, a f*ck buddy is not the same thing as a friend with benefits, because there is no underlying friendship. Carrie discovered this when she attempted to shift hers into something more serious, only to find he was boring and bland and they had nothing in common. Result? She still had no boyfriend, and now no f*ck buddy either.
Rebounding is a problem area for Carrie. After seeking out a therapist at the behest of her friends, Carrie met Seth in the waiting room at her psychiatrist's office. He inadvertently helped her make a breakthrough when he explained he had issues with using women for sex, thereby confirming what her doctor had suggested—that she does indeed pick the wrong men.
Every girl needs a guy that's just there for a good time when she's feeling down. Jeremiah, a performance artist/cater waiter, was the perfect man for the job when Carrie ran into him after Mr. Big was being a jerk at a fancy white-food-only party. They had a few pitchers of margaritas and Jeremiah came home with her. The next morning, while he was still in Carrie's bed, Big called and told her he loved her.
Carrie had a phase with younger men, Sean being one of them. She soon discovered he was bisexual, which left her a little stunned. It was a party with his friends that created the tipping point—she couldn't handle their progressive mentality about gender fluidity and a game of spin the bottle pushed her over the edge. It was more her problem than his, though.
A rare encounter in Manhattan, this guy just was not in the same place as Carrie when it came to marriage and the desire to settle down. She was overwhelmed by his commitment and momentum, he was upset by her lack thereof. He was passed off to Charlotte briefly, too, before she decided their tastes in china patterns was entirely incompatible.
Sam was young. Sam was fun. Sam was just what Carrie needed. They enjoyed a few carefree nights out together before Carrie was hit with the reality of just how young he was when she woke up in his messy, toilet-paperless apartment.
Per usual, Mr. Big showed up and snuffed out any chance of things working with Carrie and her new guy/star baseball player. They ran into Big while at a party and then Carrie ended up crying in the Yankee's mouth when he kissed her. Game over.
This guy seemed promising. He even provided a sanctuary for Carrie in the Hamptons when Charlotte got an unfortunate case of crabs. But then she ran into Big and Natasha at a party and all thoughts of Dr. Meego promptly exited her mind.
He was a suave, handsome, successful politician and he pursued Carrie with an intensity that still felt playful and fun. Things stopped being fun when he passive aggressively ended things with Carrie, citing her column as too sexual for him to be associated with. We all know he was just pissed she wouldn't agree to pee on him.
Ah, high school sweethearts. So romantic! And David Duchovny is a charmer for sure. Too bad he was a patient at a mental institute.
It's always great when you get along with your boyfriend's family. It's not so great when you get along with them better than with your boyfriend. Plus, Vaughn Wysel had performance issues in the bedroom that he refused to acknowledge or talk about with Carrie.
After dating a string of freaks, Carrie met Ben in Central Park and they hit it off. He actually seemed like a nice guy—it was Carrie who turned out to be the weird one when he caught her rummaging through his stuff in search of "something freaky."
There were sparks at first sight with Jazz musician Ray King, no matter how much Mr. Big tried to interfere with their flirtations. The relationship seemed fun enough, and they definitely had physical chemistry—but their lack of things in common and his emotional ADD left them with little more than that.
Berger was a funny and witty writer—a very insecure funny, witty writer. In the end, his own feelings of inadequacy, especially compared to Carrie's success, were too much for him to overcome. He had a logged a lot of screen time, so he's up there on the list, but he broke up with her via Post-It note, so not too up there.
Aleksandr Petrovsky may have put his art before his relationship, but he never really purported to be anything other than what he was. It was a similar scenario to Carrie's relationship with Big, where she expected a set-in-his-ways older man to suddenly change for her. That said, the Russian was significantly more romantic and expressive than Big ; he swept Carrie off her feet in a way that few, if any, of her other boyfriends ever had.
As a loyal fan of Team Aidan (now you know who #1 in this ranking is), I could never fully wrap my head around why Carrie kept hanging onto Mr. Big—he caused her so much misery and heartache on so many occasions. The only explanation I can conceive is that they were both damaged and difficult, so when they each went off to be with more stable, steady partners, it never worked because it only magnified their individual issues. However, despite all the drama and rampant insecurities he set off in her, Carrie and Mr. Big had an undeniable chemistry and magnetism that kept bringing them back together and wiping the slate clean. And ultimately, our leading lady became Mrs. John James Preston—all's well that end's well, right?
Ah, Aidan. Perfect Aidan. (Especially perfect after he ditched the boho hippie vibes and transformed into a handsome, rugged, all-American hunk.) No one cared for Carrie or tolerated more of her B.S. than this man. He was selfless, loving, and forgiving to a fault. He's the boyfriend we all wish we had, and Carrie took him for granted. To be honest, it's probably a good thing he and Carrie didn't end up together, because he definitely deserved better. He will always be #1 in our book.