Sex and the City: Ranking Carrie Bradshaw's Boyfriends

From City Comptroller hopeful Bill Kelley to 20-something Sam, Carrie Bradshaw’s (Sarah Jessica Parker) boyfriends have run the gamut from successful to scrubby, handsome to slightly less handsome, and great loves to crash-and-burn fiascos. See EW’s definitive ranking of the Sex and the City romancers, ahead.

It was the wrong time and the wrong place for Patrick Casey, who was played by Richard Joseph Paul in SATC‘s second season. The recovering alcoholic not only scarred Carrie with his cigarette butt, but embarrassed her in front of her whole block when he stripped in the street and repeatedly yelled about their tryst.

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, Howie not only gives Carrie a night of terrible sex, but calls her out in front of the entire wedding to top off the whole painful experience.

Kurt Harrington (Bill Sage) was a bit of a scumbag, but he gets minor points for being the first man we see Carrie with in the show’s 1999 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.

Dean Winters was hardly mayhem in Carrie Bradshaw’s life as John McFadden, but he sure was mediocrity. He falls short when Carrie tries to turn him from f–k buddy into boyfriend, revealing that he brings little to the table besides calling cards and sex.

If he wasn’t played by Bradley Cooper in his first-ever on-screen appearance, Jake would find himself even lower on the list. The playboy meets Carrie after the publication of her humiliating New York Magazine cover, and not only takes joy in her dubious newfound fame, but refuses to let her out of his car when she asks to leave.

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.

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 about breaks even as Carrie earned souvenirs of a custom-made Carrie comic book and a large stash of pot from their short-lived relationship.

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

When Carrie and the ladies made their way west to L.A., 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’ houses.

Jon Bon Jovi dropped in on SATC‘s second season as Seth, a man who sees the therapist Carrie spends a short time visiting. After flirting in the waiting room and playing a bit of Twister, he reveals his true colors when, in a shared moment of self-awareness, he tells Carrie that he loses interest in women after sleeping with them… while in bed, post-coitus.

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 mental facility was a bit of a roadblock in the former sweethearts’ future.

Twenty-something Sam found his way into Carrie’s circle in the show’s first season. The young, hip suitor is cute, a good kisser, and gets Carrie into all of the right clubs, but his lack of basic essentials like coffee filters or toilet paper are unacceptable.

Bill Kelley was so, so close to being the best, but in the end, was simply the worst. Played by Mad Men‘s John Slattery, he had a strong start with his Staten Island meet cute, jokes about half-points, and politician good looks, but when he slut-shamed Carrie for her sex column after asking her to indulge in his own out-there fantasies, he was out the door.

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, however, as Carrie soon found herself back in the arms of Big.

Eddie Cahill made his on-screen debut as Sex and the City‘s Sean. The bisexual 20-something is honest, kind, and brings all of the right liquid courage to an ice skating rink, but his willingness to make out with both Alanis Morissette and Michael Medico is a little too much for old-fart Carrie.

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.

Played by famed dancer Mikhail Baryshnikov, 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.

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 in one particularly crab-filled weekend. Carrie’s loss, if you ask us.

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.

When he was good, he was great; when he was bad, he was terrible. 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.

No one was more criminally underrated than The New Yankee. Carrie snagged herself MLB player Joe 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.

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 and played by Chris Noth, 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.

Aidan Shaw (John Corbett), was simply the better man. 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.