A definitive ranking of Carrie Bradshaw's 'Sex And The City' boyfriends

If you tuned into the original episodes of Sex and the City (watch here) when it ran from 1998 to 2004, you’ll recall that Carrie Bradshaw (Sarah Jessica Parker) had some pretty notable—not to mention memorable—boyfriends.

Sure, most of us recall debating Big vs. Aiden, or in later seasons characters like Berger or Petrovsky. But with And Just Like That hitting Crave this week for a brand new batch of episodes (watch now), we took a deeper dive and ranked all 24 of SJP’s love interests: from Bradley Cooper, to Vince Vaughn, to John Slattery and more.

24. Jake (Bradley Cooper)

Back in 1999, Bradley Cooper got his very first onscreen gig when his character, Jake, had a run-in with Carrie on what was maybe one of the worst days of her life. Jake was a fun-loving guy who was in it for the good times, even after Carrie’s cover shoot for New York Magazine went horribly wrong. While it’s fun to go back and see the accomplished actor-director in the role now, at the time, he was one of the skeeziest dudes Carrie's ever been involved with.

23. Kurt Harrington (Bill Sage)

When SATC first debuted, it was the one and only Kurt Harrington who set the tone for what kind of a series the show would first be: women taking back their sexuality in the big city. For a long time, Kurt had strung Carrie along, until she finally decided to have sex "like a man." At first, her gamble appeared to work and Kurt was into it, until Carrie realized no strings was all she’d ever get from this guy. Thankfully, she finally decided to move on.

22. Wade Adams (Cane Peterson)

It’s one thing to be a kid at heart. It’s another to be a man-child pretending to be grown-up while still attached to your mom’s apron strings. That’s the situation Carrie found herself in when she dated comic book store owner Wade back in Season 3. Look, there’s nothing wrong with living with your parents (have you looked at the real estate market lately?), but there’s nothing cool about lying to your girlfriend and then throwing her under the bus. That’s actually the opposite of a superhero, Wade.

21. Keith Travers (Vince Vaughn)

When the crew headed to Los Angeles in Season 3, Carrie proved that she certainly knows how to pick 'em when she fell under the spell of one Keith Travers. The guy pretended to represent Matt Damon and brought Carrie back to his fancy house, only for Carrie to learn that Keith was actually Carrie Fisher’s assistant and he was squatting at her pad. Not cool, Keith. Not cool.

20. Bill Kelley (John Slattery)

Carrie certainly tried to make a go out of this relationship with the politically savvy Bill Kelley back in Season 3, but when he asked her to pee on him during sex, the writing was on the wall. Later, when Carrie revealed she didn’t think she could go through with it, Bill responded by breaking up with her because it wasn’t a good look for him to be dating a sex columnist. Can you say gross?

19. Howie Halberstein (Bryan Callen)

This sixth-season episode is enough to make anyone think twice about getting intimate with a fellow member of a wedding party. When Charlotte and Harry married, Carrie decided hooking up with Howie was a good idea. Unfortunately, not only was the sex so bad that Carrie wound up injured from it, but Howie also used his speech as an opportunity to publicly slam her. Cringe, cringe, and also a side of cringe.

18. Seth (Jon Bon Jovi)

If you ever needed more proof to maybe not date the guy you met at your therapist’s office, this second-season episode is it. In it, Carrie begins dating Seth, and at first, he seems like a normal, nice guy. But before long he lets his true colours fly: his deal is that he loses interest in women after he sleeps with them. Look, we’ve all got our issues, but the fact that he told Carrie this after a romp in bed with her is definitely not a good look. 

17. Patrick Casey (Richard Joseph Paul)

Recovering alcoholic Patrick wasn’t a bad guy per se. But the way the writers tackled his addiction is definitely cringeworthy stuff. So when Carrie broke up with him and he relapsed (naked, on her street), everyone hoped that this storyline would just be over already. And thankfully, it was.

16. Jack Berger (Ron Livinston)

Was Carrie’s fellow writer boyfriend charming? Undoubtedly. He was also cute, smart and good with her friends. Unfortunately, he also couldn’t take dating someone who was more successful than he was, and he definitely couldn’t withstand a little criticism (even if, now, years later, scrunchies are finally making a comeback). But the worst part of all? He broke up with Carrie on a Post-It note. A Post-It note, people! 

15. Ray King (Craig Bierko)

Was jazz-lover Ray the best that Carrie ever had in bed? Oh, she’d probably sing home about that one. Unfortunately, the pair were never able to go deeper than that though, since the character had ADHD. Ray seemed like a nice guy and all, but between the problematic storyline and the fact that it lasted for two Season 4 episodes, we can’t really place him any higher on this list.

14. John McFadden (Dean Winters)

Is dating your friend with benefits ever a good idea? Carrie decided to put this one to the test back in Season 2 when she pushed for more with John. Sure, they had a physical attraction going for them, but as Carrie quickly discovered, that was where it ended. Look, there was nothing wrong with John and he seemed like an okay guy, but when you offer free cell phone minutes on a date as a gift, things can only go downhill from there.

13. Gilles (Ed Fry)

Everything seemed to be coming up Carrie when she met Gilles back in Season 1. The Frenchman charmed her, wined her and dined her, and gave her one of the most romantic weekends of her life. He also unexpectedly left her alone in a hotel room with an envelope full of cash, leading Carrie to wonder if he thought she was an escort, or just in need of a handout. Ugh.

12. Aleksandr Petrovsky (Mikhail Baryshnikov)

Ah, the Russian. Sure, there was something charming about the guy, which is why Carrie dated him in the first place. He was the “man” she’d been looking for all this time. But at his core, Petrovsky only liked the idea of Carrie, and he didn’t really accept her for who she was. That was never clearer than when the pair moved to Paris, but luckily Carrie wised up… eventually.

11. Jeremiah (Sam Ball)

This poor cater waiter never really stood a chance when Carrie met him back in Season 2. Sure, he was cute, charming, and had a strategically placed tattoo, but by that point, Carrie had already fallen for Mr. Big and his charms. In the end, we never really got to know Jeremiah since shortly after he and Carrie slept together, Big finally came around, but to this day we kind of wish he’d stuck around longer.

10. Sean (Eddie Cahill)

If ever there were a case to be made for not being too thirsty, Sean, a.k.a. “the marrying kind” was it. He was a nice, respectable guy and all, but in the end, he really wanted to find “the one” while Carrie was only “trying him on for size.” It was definitely not a fit, and Carrie quickly pointed him towards Charlotte, only for them to later fizzle out over China patterns.

9. Sam (Timothy Olyphant)

Oh, Sam. Remember the pretty young thing with the completely disgusting apartment? He was a sweet kid with a big heart, but he was definitely years behind where Carrie was when the two briefly got together in Season 1. Also, as much as we still have his impromptu “Unicorn Woman” song stuck in our heads, we’ll never forgive him for believing that toilet paper and coffee filters are interchangeable. 

8. Willie Applegate (Wallace Langham)

Poor Willie just couldn’t catch a break. Not only did he show up for his Season 6 date with Carrie with a stye in his eye, but he knocked over the table. Add in the fact that he was just a “simu-date” for Carrie, who was really interested in Berger, and we couldn’t help but feel for the guy.

7. Dr. Bradley Meego (Patrick Breen)

Ever wonder what happened to the “good on paper” doctor from the Hamptons that Carrie dated back in Season 2? It’s okay if you haven’t—not many fans remember the character at all. Sure, Dr. Meego was cute and successful, but Carrie also forgot about the guy shortly after she ran into Big and his new girlfriend Natasha following the pair’s return from Paris.

6. Vaughn Wysel (Justin Theroux, in his second of two different appearances)

This writer and his amazing family seemed to fit Carrie like a glove… until they got into the bedroom that is. Even though Carrie was willing to work with Vaughn and figure out his… shortcomings, Vaughn’s inability to open up solidified the end. We don’t know whose hearts were hurt worse by it all: ours, Carrie’s, Vaughn’s, or Vaughn’s amazing mother (played by Valerie Harper).

5. Jeremy (David Duchovny)

Sometimes the past is better left in the past. Carrie discovered this the hard way when she tried to reconnect with her high school boyfriend, Jeremy. At first, things seemed like they were going to pick right back up where they left off, but then Jeremy revealed he had checked himself into a psychiatric facility. Good on him for taking care of his mental health, but that’s clearly not the right time to be starting a new (or rekindled) relationship with anyone. 

4. Joe Stark (Mark Devine)

A professional athlete who’s nice, funny and into you? It seems like a dream come true, until you realize you’re not fully over your ex, after all. Big had done a number on Carrie by the Season 2 premiere, which meant her relationship with this Yankee was never going to last. Still, he seemed like a stand-up guy, and we wish he’d had a swinging chance.

3. Ben (Ian Kahn)

Oh Ben, how we barely knew thee. This Season 2 character was probably the one normal guy that Carrie dated back in the earlier years of the show. But when she started going through his apartment looking for some kind of inner freak (because obviously, it seemed too good to be true), Ben took matters into his own hands and broke up with Carrie. Can you blame him?

2. Mr. Big (Chris Noth)

Considering Big was “the one” for Carrie in the end, we couldn’t really rationalize putting him any lower on this list. Still, he doesn’t earn our top spot for the simple reason that he treated our gal like hot garbage on more than one occasion. Sure, the heart wants what it wants and in the end, if Carrie was happy, so are we (kind of). For now, let’s just say there’s lots more to unpack in And Just Like That... for multiple reasons #IfYouKnowYouKnow. 

1. Aidan Shaw (John Corbett)

Was there anything not to love about Aidan Shaw? He was nice, he treated Carrie and her friends like gold, he was besties with Steve, he had a dog, and he even made his own furniture. There were more than a few fans who felt like Carrie threw away the best thing that ever happened to her when she cheated on this guy, but the good news is that, in the end, at least we know Aidan got the happy ending (and family) he always deserved.

Catch the latest episodes of And Just Like That, streaming now on Crave. 

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