A Definitive Ranking of Every Guy Carrie Bradshaw Dated

All 28 of them.

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.

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28. Keith Travers

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.

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27. Patrick Casey

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. 

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26. Howie Halberstein

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. 

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25. The Man with Two Faces

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. 

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24. PJ aka The Man with No Soul

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?? 

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23. The Man Who Steals Cheap Used Books for No Reason

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. 

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22. Kurt Harrington

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.

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21. Willie Applegate

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. 

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20. Wade Adams aka Superboy

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. 

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19. Jake

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. 

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