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Sex and the City’s original six-season run followed a group of thirtysomething besties looking for love in New York City. Most notably, the series followed the love life of Carrie Bradshaw (Sarah Jessica Parker), who narrated the series via her newspaper column.
Carrie’s dating history featured everything from one-night stands to failed romances to fun flings to big, long-term loves. There were 28 different men throughout the series that Carrie dated and/or slept with, and among them were a few gems and a few jerks. As the new series And Just Like That premieres on HBO Max, here’s our list of Carrie Bradshaw’s five best and five worst boyfriends.
5. Bill Kelley aka ‘The Politician’
Played by Mad Men star John Slattery, Bill Kelley was a handsome, successful politician who was running for city comptroller. His relationship with Carrie seemed promising, with a strong start at their Staten Island meet cute. At campaign events, she played the role of a politician’s girlfriend perfectly wearing vintage Halston.
But after Carrie turned down his request to indulge in his sexual kink, he slut-shamed her for her sex column — saying it was bad for his career. This relationship went from one of Carrie’s best to one of her worst in the blink of an eye.
4. Ray King
Carrie definitely had physical chemistry with jazz musician Ray King (Craig Bierko), nicknamed Pork Pie by Mr. Big. He introduced her to his musical genre, complete with chic downtown bars and a hip way of life. Carrie also bragged that Ray was the absolute best she’d ever had in bed.
But Ray was a love him or hate him type of guy. His entire character centered around his jazz obsession, and he never let anyone forget that he owned his own club. Ultimately, their lack of things in common and his hyperactivity associated with his ADHD made it clear to Carrie that Ray wasn’t boyfriend material.
3. Vaughn Wysel
In season 2 of Sex and the City, Carrie met someone who appeared to be her perfect match. Vaughn Wysel — played by Justin Theroux — was a celebrated, handsome short-story writer who was both charming and funny. He was also part of an amazing family — who Carrie got along famously with — led by matriarch Wallis Wysel (Valerie Harper).
The only negatives when it came to Vaughn were his performance issues in the bedroom. He refused to acknowledge them — much less talk about them — with Carrie. Ultimately, she realized she had a better relationship with Wallis, and she and Vaughn broke up.
2. Keith Travers
When Carrie headed out to California in season 3, she met Keith Travers (Vince Vaughn) at a Hollywood premiere after-party. The tall and handsome Keith told Carrie he was a big-time Hollywood agent who “represented” Matt Damon.
But as it turned out, everything that came out Keith’s mouth was a lie — his job, his income, his entire life. After their hookup, Carrie and Keith were caught in bed at Carrie Fisher’s house — a place Keith had claimed was his own. But the truth was he was Fisher’s assistant, so Carrie left in a hurry and never saw Keith again.
1. Mr. Big
We are going to ruffle some serious feathers here, but when it comes to boyfriends Mr. Big (Chris Noth) was the worst. Also known as John James Preston, Mr. Big was THE relationship in Carrie’s life throughout Sex and the City’s six seasons. He was introduced in the pilot, and ultimately won Carrie’s heart in the finale.
But they were off and on constantly, he was selfish and emotionally distant, and she wanted something that he couldn’t give her. He was also married at one point and Carrie was the other woman!
Yes, Mr. Big was funny and charming. And his banter with Carrie made it clear that they were friends who cared about each other. But why did Carrie keep hanging on to this guy? He caused her so much misery and heartache, but she kept going back to him. And, he informed every one of her other relationships.
Yes, Carrie ultimately became Mrs. John James Preston. But if the rumors about And Just Like That are true, she will soon be just another ex-wife.
5. Aleksandr Petrovsky
Let’s be honest, Carrie’s relationship with Aleksandr Petrovsky (Mikhail Baryshnikov) was never going to last. He put his art before everything else in his life, and he was an older man set in his ways. Carrie was never going to change him. So instead, she changed every part of her life to fit into his world. Which is never a good idea.
What made Aleksandr so great, though, was that he was always very straightforward with Carrie about who and what he was. He was a romantic who swept her off her feet, but he wasn’t interested in a wedding and having more children. Still, Aleksandr is one of the best boyfriends Carrie ever had because he was so honest with her.
After a series of bad dates in season 1, Carrie found herself a nice and normal guy named Ben at the beginning of season 2 of Sex and the City. He was the editor of a “hip political magazine” who appeared to be genuinely interested in Carrie and really liked her.
But ultimately, Ben was a missed opportunity for Carrie and she ended up being the crazy one in this relationship. Ben dumped Carrie after catching her tearing apart his apartment while looking for proof that he was secretly freaky and weird.
3. Joe Stark
Just before she met Ben, Carrie had a brief relationship with New York Yankee Joe Stark. The duo immediately hit it off, and they even ended up on Page Six together. But Carrie still had feelings for Mr. Big, and of course, he showed up to squash any chance of things working out with the star baseball player.
After Joe and Carrie ran into Big at a party, she ended up crying in the Yankee’s mouth when he kissed her. And that was that.
2. Jack Berger
Some Sex and the City fans probably think that I’ve made a serious error with number two on the best boyfriend list. Many will argue that Jack Berger (Ron Livingston) should be number one on the worst list and Mr. Big should be number two on the best list. It’s almost as if we accidentally switched them. But, we didn’t!
Berger was a funny, charming, and witty writer who had a lot in common with Carrie. He also dished out amazing advice to her friends — Miranda needed to hear that “he’s just not that into you.”
But his feelings of inadequacy compared to Carrie’s success were too much for him to handle. He also had issues with jealousy and had ex-girlfriend baggage. He was a good guy, but not the right boyfriend for Carrie. And breaking up via Post-It note was not his best look.
1. Aidan Shaw
Every Sex and the City fan had to know this was coming. By far, without a doubt, the best Carrie Bradshaw boyfriend was the perfect Aidan Shaw (John Corbett). Especially when he ditched his hippy, furniture maker look for the rugged, handsome entrepreneur vibe. He was warm, loving, and ready for a serious commitment.
But as perfect as Aidan was, he was way too good for Carrie and she didn’t deserve him. This man put up with Carrie’s B.S. like no other. He was kind, selfless, and forgiving — and Carrie took it all for granted.
Aidan made Carrie a better person, and he was the boyfriend every girl wishes they had. But instead of choosing Aidan and his country house, dog, and never-ending values and morals, Carrie opted for Mr. Big.
Fans will see how that relationship ultimately worked out in And Just Like That, the Sex and the City reboot which is now playing on HBO Max.
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