Sex And The City: Carrie Bradshaw’s Top 11 Boyfriends


Television history overflows with central male characters dating woman after woman after woman. Finally, in 1998, Carrie Bradshaw strapped on her Manolo Blahniks and flashed her flamboyant fashions to flip that stereotype on its head in HBO’s hit series Sex and the City. In the very first episode, she and her girlfriends vow to start having sex “like men.” But it was not just about the sex. Carrie was very much an old-fashioned girl, albeit a forward-thinking one, looking for true love and writing a column about it. It took her six seasons, dozens of love interests and two movies to find it, but she did. Here are her top 11 boyfriends.

11. Jack Berger

It’s probably safe to say Berger is the most hated man in the history of the show. But that’s only because he seems so good, but then turns so… cowardly. First appearing in season five, episode five, he seems age-appropriate. He’s an author; he’s tall, dark and handsome; he rides a motorcycle. Unfortunately, when they first meet, he has a girlfriend and he goes away for a while, resurfacing at the end of the season, when he’s unattached. As season six opens, they finally start dating and they have pretty good chemistry – everywhere, but the bedroom. He soon gets cranky when she criticizes his use of scrunchies in his book, and he gets jealous when her book does well and his publisher drops him. Then come the games: he says he wants to take a break, then he wants back in and then, the pièce de résistance, he breaks up with her on a Post-It note. Nice.


10. Aleksandr Petrovsky

This was a close call for all the Big fans out there. There were just nine episodes to go in the series when Carrie met famous Russian artist Aleksandr Petrovsky, an older man, in season six, episode 12. It’s a little more of an old-fashioned romance for Carrie, as they don’t really get together until his second episode. Things do get a little shaky by his third appearance though, when it comes to light that he has a 22-year-old daughter and isn’t into becoming a daddy again at his age. It’s actually a little surprising he lasted so long and that they came so close to really being something, because there were so many other red flags. He’s weirdly open about death; she feels awkward around his friends; his art is his priority; it takes a long time for him to meet her friends; and he wants her to leave her beloved NYC for Paris. Shockingly, she goes. Not shockingly, she doesn’t like it and comes home to Mr. Big.

 9. Howie Halberstein

Charlotte and Harry are finally getting married in season six, episode eight, and Carrie is seriously on the rebound after her “sticky” breakup with Berger. She meets Harry’s best man, Howie, who makes her laugh – and boy did she need a laugh. His name alone is funny. Howie Halberstein. He’s tailor-made for comic relief, both for Carrie and the audience. Unfortunately for Carrie, the comic relief culminates in the bedroom, which was no relief to her. He performs like a rabbit. All speed, no style. This episode is called “The Catch,” and Howie Halberstein is clearly not a catch in Carrie’s book. But he gave her some laughs.

 8. Seth

Remember that brief time in the late-90s/early-2000s when Jon Bon Jovi tried to be an actor? Season two, episode 13 was his first real high-profile acting gig. How well did it go? Well, it led to a 10-episode arc on Ally McBeal and stretching out the old acting chops on The West Wing and 30 Rock to play… Jon Bon Jovi. Here, Carrie can’t stop whining about her breakup with Mr. Big. Her friends convince her to seek therapy, where she’s told she picks the wrong men, and it’s there that she runs into Mr. You Give Love a Bad Name. That can’t bode well. And it doesn’t. They play Twister; they do the deed; and he tells her the reason he’s in therapy is he loses interest in women after the deed is done. But at least Carrie had her rebound fling.

7. Bill Kelley

Before John Slattery was “silver-haired rich guy with a penchant for younger women” Roger Sterling on Mad Men, he had a fun little arc as “silver-haired rich guy with a penchant for younger women” Bill Kelley during the third season of Sex and the City. Bill is a politician on the campaign trail and Carrie is committed to be by his side through it all. Publicly, everything’s cool. Privately, very privately, things are less than cool. In fact, they’re warm, wet and uncomfortable. Bill is what has become a bit of a stereotype in the real world: the kinky politician. He likes to be peed on. Carrie, needless to say, doesn’t want to pee on him. It leads to Carrie’s great line, “It’s practically a fairy tale: the princess and the pee.” But the relationship wasn’t a fairy tale and after three episodes it was flushed down the toilet.

6. Vaughn Wysel

Writers, right? As we saw with Berger at the top of the list, two writers in love can lead to some rocky waters. Sometimes one is more like oil in the other’s water and the whole thing just doesn’t mix. Well, here, in season two, episode 15, our intrepid columnist has hooked up with another writer played by Justin Theroux. He’s big on family and takes Carrie to meet his. They love her, she loves them. After lunch, Carrie and Vaughn are feeling randy and get down to business. But Vaughn’s boys… leave the business meeting a little early. If you catch our drift. Later, they try again. And again the train leaves the station before there are even any passengers aboard. Obviously, this creates some tension and this relationship… ends prematurely.

 5. Keith Travers

Sometimes it’s the guest star that makes the love interest memorable. And few actors steal scenes like Vince Vaughan. In season three, episode 14, Carrie has left her true love, New York City, for Los Angeles discuss the possibility of turning her column into a movie. There, she meets Keith, all smooth-talking, six-foot-five of him. Part of his smooth talk is that he’s a high-powered Hollywood agent; a superstar movie star schmoozer. Turns out, all it is is smooth talk – it’s all lies. Carrie finds this out in the midst of some hot and heavy times with Keith in a fancy Hollywood home, which happens to be owned by another great Carrie, Carrie Fisher, who walks in on them. Keith was fun, but a fraud.

 4. Wade Adams

Carrie is nothing if not trend-savvy. In season three, episode 15, Carrie anticipates the current “geek chic” trend by dating against type when she meets Wade, a comic-book store clerk. Although he’s more good looking than she might have expected a comics-obsessed guy to be, he does fall into stereotype mode on most other fronts. He’s a kid at heart, and Carrie enjoys the change of pace at first, but he also lives with his mother. And that kind of gets in the way of the “sex” part of Sex and the City.

 3. Jeremy

In season six, episode 10, Carrie bumps into Fox Mulder – er, Jeremy, her high school sweetheart, played by Mr. X-Files himself, David Duchovny. She finds him at their high school reunion and is pleasantly surprised that he’s turned into a strapping, paranoid FBI agent – er, seemingly well-adjusted dude, who’s been living in Denver. They kiss. Carrie later tells Samantha she only broke up with him in high school because she thought there had to be better guys out there. But, she feels, it’s starting to seem like there aren’t. Whether or not there were better guys out there remained to be seen, but the truth was definitely out there. Carrie invites Jeremy over to “watch a movie” (aka, seduce him), when he comes clean: he’s headed to a mental institution. Ultimately, she’s okay with that and they go all the way. But he still had to go away.

 2. Aidan Shaw

TV viewers already knew John Corbett as the immensely likable “Chris in the Morning” on Northern Exposure. So when he brought his unassuming confidence and sensitive manliness into Carrie’s world, we were ready for something good. But was he too good? He’s anti-smoking, he doesn’t want to jump right into the sack, he makes beautiful furniture for Charlotte’s wedding gift, he’s just a nice guy. And what does Carrie do? She sleeps with Big. Her conscience gets the better of her and she confesses, but that’s it for Aidan. This may have been the one instance where even die-hard fans were angry with Carrie. Aidan was just so dang likeable.

 1. Mr. Big (aka John James Preston)

Obviously, Big was “the one.” From the very first episode, she couldn’t quit him. They were on-again, off-again, like so many great TV couples. He’d been divorced, married another woman and she had her relationships and flings. They had that affair while she was with Aidan. He often seems non-committal or distracted, and he moves away from her twice, but he clearly cares for her. He’s immensely charming and their chemistry is undeniable. In the end, he finds her in Paris and declares his love – and we finally learn his first name. Carrie has two great loves in this series that she just can’t live without: Big and New York City. And she proves that in the final episode when she leaves Aleksandr and Paris for Big and the Big Apple.