We couldn't help but wonder: Which suitors truly swept Carrie off her Manolos...and which were just footnotes? Ranking Carrie Bradshaw's boyfriends from Sex and

We couldn't help but wonder: Which suitors truly swept Carrie off her Manolos...and which were just footnotes?

Ranking Carrie Bradshaw's boyfriends from Sex and the City, from worst to best

We couldn't help but wonder: Which suitors truly swept Carrie off her Manolos...and which were just footnotes?

By Madeline Boardman

Madeline Boardman

Madeline Boardman is a former digital features director at **. She left EW in 2017.

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and James Mercadante

September 3, 2025 8:30 a.m. ET

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John Corbett as Aidan Shaw on 'Sex and the City'; Chris Noth as Mr. Big on 'Sex and the City'; Bradley Cooper as Jake on 'Sex and the City'. Credit:

Craig Blankenhorn/HBO; HBO (2)

When you think of the great loves of Carrie Bradshaw's (Sarah Jessica Parker) glamorous, jog-walking-through-Manhattan life on *Sex and the City*, the usual suspects come to mind: Aidan (John Corbett), the Russian (Mikhail Baryshnikov), and, of course, Mr. Big (Chris Noth). But for a writer mining her and her friends' sexual rendezvous for her wildly popular titular column, playing the New York City dating game is part of the gig.

Across six seasons on HBO from 1998 to 2004, Carrie cycled through man-children, playboys, potheads, incompatible "f---buddies," and more than enough publish-worthy material before finding that "ridiculous, inconvenient, consuming, can't-live-without-each-other love."

With *And Just Like That* having wrapped up her story for good in August 2025 (and because fans have been debating her endgame since the Clinton administration), we've done our own investigative work to rank every short fling, one-nighter, and legit relationship to see who *really* deserved TV's NYC It Girl. (And no, *AJLT* storylines do not count!)

26. Patrick Casey (Richard Joseph Paul)

Richard Joseph Paul as Patrick Casey on 'Sex and the City'.

It was the wrong time and the wrong place for Patrick Casey, who Richard Joseph Paul played in *SATC*'s second season. The man recovering from his alcohol problem not only scarred Carrie with his cigarette butt, but he also embarrassed her in front of her whole block when he stripped in the street and repeatedly yelled about their tryst. —*Madeline Boardman*

25. Howie Halberstein (Bryan Callen)

Bryan Callen as Howie Halberstein and Sarah Jessica Parker as Carrie Bradshaw on 'Sex and the City'.

Howie Halberstein (Bryan Callen) may have looked like a promising weekend fling when he entered Carrie's life in the show's sixth season, but he quickly took a turn. A friend of Harry's (Evan Handler), Howie not only gave Carrie a night of terrible sex, but also called her out in front of an entire wedding to top off the whole painful experience. —*M.B.*

24. Kurt Harrington (Bill Sage)

Bill Sage as Kurt Harrington on 'Sex and the City'.

Kurt Harrington (Bill Sage) was a bit of a scumbag, but he gets minor points for being the first man we saw Carrie with in the show's 1998 premiere episode. While he was hardly a stand-up gentleman, he gave Carrie what she needed: a lovely afternoon in bed and fodder for her column. —*M.B.*

23. Louis LeRoy (Daniel Sunjata)

Daniel Sunjata as Louis Leroy on 'Sex and the City'.

Season 5 found single Carrie romanticizing the hell out of her single era, but when Fleet Week came around (a.k.a. seven days of military ships docking and sailors flooding Manhattan), a little fling was still on the horizon. And the complimentary and polite Louis LeRoy (Daniel Sunjata) was the perfect guy to woo her.

He might've ranked higher if we'd gotten to know him past a few spins on the dance floor, but her time with Louis was, you know, *fleeting*. We do learn that he's not a fan of the Big Apple's noise and trash, and he leaves Carrie with his belief that everyone gets one great love in a lifetime. For her, that might just be NYC itself...and she "can't have nobody talkin' s--- about my boyfriend." —*James Mercadante*

22. John McFadden (Dean Winters)

Dean Winters as John McFadden on 'Sex and the City'.

Dean Winters was hardly mayhem in Carrie Bradshaw's life as John McFadden, but he sure was mediocrity. He fell short when Carrie tried to turn him from f--- buddy into boyfriend in a season 2 episode, revealing that he brought little to the table besides calling cards and sex. —*M.B.*

21. Jake (Bradley Cooper)

Bradley Cooper as Jake on 'Sex and the City'. HBO

If he weren't played by Bradley Cooper in his first-ever onscreen appearance, Jake would find himself even lower on the list. The playboy met Carrie in season 2 after the publication of her humiliating *New York Magazine* cover, and not only took joy in her dubious newfound fame, but refused to let her out of his car when she asked to leave. —*M.B.*

20. Gilles (Ed Fry)

Ed Fry as Gilles on 'Sex and the City'.

Gilles (Ed Fry) had foreign sophistication, a dreamy accent, and a lavish hotel room, but he disappeared without leaving a number in *SATC*'s first season. Carrie did get $1,000 and a date to remember out of the whole experience, and Gilles gains points for being a charming European architect and for buying Carrie's friends breakfast the next morning. —*M.B.*

19. Wade (Cane Peterson)

Sarah Jessica Parker as Carrie Bradshaw and Cane Peterson as Wade on 'Sex and the City'.

Wade (Cane Peterson) was a bit of reckless fun for Carrie in *Sex and the City*'s third season. The overgrown man-child still lived with his parents and blamed Carrie for the weed in his house when his mom showed up, but he almost broke even as Carrie earned souvenirs of a custom-made Carrie comic book and a large stash of pot from their short-lived relationship. —*M.B.*

18. Derek "The Bone" (Andrea Boccaletti)

Andrea Boccaletti as Derek 'The Bone' on 'Sex and the City'.

With a nickname like "the Bone," it's only natural to assume Stanley's (Willie Garson) drop-dead-gorgeous, most important client — Derek (Andrea Boccaletti), the world's biggest underwear model who goes through life "like he travels with his own personal lighting director" — would be the perfect one-night stand.

And while he was *technically* a one-nighter, it wasn't in the way you'd think. In the series' second episode, Carrie and Derek spend the night in her bed talking about insecurities, loneliness, future goals, and trading sweet compliments, proving to her that someone *that hot* can be down to earth, too. —*J.M.*

17. Ray King (Craig Bierko)

Chris Noth as Mr. Big, Craig Bierko as Ray King, and Sarah Jessica Parker Carrie Bradshaw on 'Sex and the City'.

Played by Craig Bierko in season 4, Ray King was a love-him-or-hate-him type fellow — Carrie loved him (at first) and Mr. Big hated him (always). The musician introduced Carrie to jazz, chic downtown bars, and his hip way of life, but also brought his hyperactivity and his lack of boyfriend material into the picture. —*M.B.*

16. Keith Travers (Vince Vaughn)

Vince Vaughn as Keith Travers on 'Sex and the City'.

When Carrie and the ladies made their way west to L.A. in season 3, they met Keith Travers (Vince Vaughn), a man who "represented" Matt Damon. He and Carrie spent a couple of dreamy days partying in V.I.P. rooms and scouting out stunning California real estate, but with the surprise arrival of Carrie Fisher, it was soon revealed that he was nothing more than an assistant squatting in his boss' house. —*M.B.*

15. Seth (Jon Bon Jovi)

Sarah Jessica Parker as Carrie Bradshaw and Jon Bon Jovi as Seth on 'Sex and the City'.

Jon Bon Jovi dropped in on *SATC*'s second season as Seth, a man who saw the therapist Carrie spent a short time visiting. After flirting in the waiting room and playing a bit of Twister, he revealed his true colors when, in a shared moment of self-awareness, he told Carrie that he loses interest in women after sleeping with them...while in bed, post-coitus. —*M.B.*

14. Jeremy (David Duchovny)

David Duchovny as Jeremy and Sarah Jessica Parker as Carrie Bradshaw on 'Sex and the City'.

Carrie found herself falling for her high school boyfriend, Jeremy (David Duchovny), once more in *SATC*'s sixth season. While he proved he wasn't a loser and they finally rounded the bases, Jeremy's place of residence in a Connecticut facility that provided mental health services was a bit of a roadblock in the former sweethearts' future. —*M.B.*

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13. Sam (Timothy Olyphant)

Sarah Jessica Parker as Carrie Bradshaw and Timothy Olyphant as Sam on 'Sex and the City'.

Twentysomething Sam (Timothy Olyphant) found his way into Carrie's circle in the show's first season. The young, hip suitor was cute, a good kisser, and got Carrie into all of the right clubs, but his lack of basic essentials like coffee filters or toilet paper was unacceptable. —*M.B.*

12. Bill Kelley (John Slattery)

John Slattery as Bill Kelley and Sarah Jessica Parker as Carrie Bradshaw on 'Sex and the City'.

Craig Blankenhorn/HBO

Bill Kelley was so, so close to being the best, but in the end, was one of the worst. Played by *Mad Men*'s John Slattery in the first two episodes of season 3, Bill had a strong start with his Staten Island meet-cute, jokes about half-points, and politician good looks, but when he shamed Carrie for her sex column after asking her to indulge in his own out-there fantasies, he was out the door. —*M.B.*

11. Jeremiah (Sam Ball)

Sam Ball as Jeremiah on 'Sex and the City'.

Jeremiah (Sam Ball) had potential: He was an acclaimed performance artist, he had cool tattoos, he still managed to pay the bills with his side hustle as a cater waiter, and he could do a mean rendition of Three Dog Night's "Joy to the World." He never got his full due in season 2, however, as Carrie soon found herself back in the arms of Big. —*M.B.*

10. Sean (Eddie Cahill)

Eddie Cahill as Sean on 'Sex and the City'.

Eddie Cahill made his onscreen debut as *Sex and the City*'s Sean in season 3. The bisexual twentysomething was honest, kind, and brought all of the right liquid courage to an ice skating rink, but his willingness to make out with both Alanis Morissette (as Dawn) and Michael Medico (as Mark) was a little too much for Carrie. —*M.B.*

9. Sean (Scott Rabinowitz)

Scott Rabinowitz as Sean on 'Sex and the City'.

Sean (Scott Rabinowitz) had all of his ducks in a row — maybe a little too neatly. The investment firm owner Carrie's married friends sprung on her in season 1 was husband material on paper: well-off, brand new Upper West Side apartment, already dreaming of kids (he even bought a crib mobile).

But as Carrie put it, he's a "flesh-and-blood equivalent of a DKNY dress. You know it's not your style, but it's right there, so you try it on anyway." One try-on later, she knew he didn't fit, but Charlotte was happy to take him for a whirl...at least until she saw his taste in China patterns. —*J.M.*

8. Vaughn Wysel (Justin Theroux)

Justin Theroux as Vaughn Wysel and Sarah Jessica Parker as Carrie Bradshaw on 'Sex and the City'. HBO

Season 2's Vaughn Wysel (Justin Theroux) had a lot going for him: He was a celebrated short story writer who was cute enough to earn a spread in *GQ*; he was charming and funny; and he had an amazing family led by matriarch Wallis Wysel (impeccably portrayed by Valerie Harper).

The only thing not working with him was his body, which failed both Vaughn and Carrie in the bedroom. His unwillingness to face the issue at hand was simply the nail in the disappointing coffin. —*M.B.*

7. Aleksandr Petrovsky (Mikhail Baryshnikov)

Sarah Jessica Parker as Carrie Bradshaw and Mikhail Baryshnikov as Aleksandr Petrovsky on 'Sex and the City'.

Craig Blankenhorn/HBO

Played by famed dancer Mikhail Baryshnikov in season 6, Aleksandr Petrovsky came very close to being one of Carrie's great loves. The Russian artist literally swept her off her feet, but, when it came down to it, his work was his ultimate *lov-ah* and he was unwilling to have more children. We couldn't help but wonder, would that be enough for Carrie? No, the answer is no. —*M.B.*

6. Dr. Bradley Meego (Patrick Breen)

Patrick Breen as Dr. Bradley Meego on 'Sex and the City'.

Bradley Meego was actually a little bit of a dream date: He was a doctor with a house in the Hamptons, for crying out loud! If that wasn't enough, he was cute and kind and came to Carrie's rescue on one particularly crab-filled weekend during season 2. Carrie's loss, if you ask us. —*M.B.*

5. Ben (Ian Kahn)

Ian Kahn as Ben on 'Sex and the City'.

In a rare moment of romantic ineptitude, Carrie completely blew her chances with Ben (Ian Kahn). She was the "freak" in question in season 2's "The Freak Show," when she let her past tribulations get the best of her and went on a tear, snooping through all of Ben's stuff.

While we didn't learn much about the political magazine editor, his thoughtful demeanor, Cub Scout values, and even temper in dealing with Carrie were enough to give him a second look. —*M.B.*

4. Jack Berger (Ron Livingston)

Ron Livingston as Jack Berger on 'Sex and the City'.

When he was good, he was great; when he was bad, he was *terrible*. During his season 5–6 arc, Jack Berger (Ron Livingston) had a lot in common with Carrie, from his profession as a writer to his flair for the dramatic. While his floppy hair, impressive intelligence, and boyish charm were all assets for the brooding creative, his ex-girlfriend baggage, jealous streak, and authorship of the world's most biting Post-it knock him down a few pegs. —*M.B.*

3. Joe (Mark Devine)

Mark Devine as Joe on 'Sex and the City'.

No one was more criminally underrated than the new Yankee. Carrie snagged herself MLB player Joe (Mark Devine) in *SATC*'s season 2 premiere, but, just like always, her roller-coaster relationship with Mr. Big got in the way. The athlete could've been perfect for Carrie with his dashing good looks, sense of humor, and coveted place in society, but after Carrie cried in his mouth, the end was near. —*M.B.*

2. John James Preston, a.k.a. Mr. Big (Chris Noth)

Chris Noth as John James Preston, a.k.a. Mr. Big, and Sarah Jessica Parker as Carrie Bradshaw on 'Sex and the City'.

Craig Blankenhorn/HBO

In the storied race of Carrie's great loves, there's only one winner, and it isn't Mr. Big. Finally revealed to be John James Preston, the businessman who was first introduced in the pilot won Carrie's heart in the end — but he isn't quite the best contender. Big was selfish, emotionally distant, and always looking for his next piece of arm candy...but then again, so was Carrie. —*M.B.*

1. Aidan Shaw (John Corbett)

John Corbett as Aidan Shaw on 'Sex and the City'.

Craig Blankenhorn/HBO

Aidan Shaw was simply the better man. First showing up in season 3, the gorgeous furniture designer (come on, he made his *own* furniture!) loved Carrie above all else, and he made her a better person through the relationship. The greatest man, he even had a dog, a country house, and more values and morals than Big could fit in his sprawling Manhattan apartment. —*M.B.*

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