All 28 of Carrie Bradshaw's boyfriends in 'Sex and the City,' ranked

Erin McDowell
·16 min read
sex and the city
Aleksandr Petrovsky is a widely debated character among "Sex and the City" fans. Mark Mainz/Getty Images

Jim was Carrie's ex before he began dating Miranda.

jim sex and the city
Jim. HBO

Appeared in: Season 3, episode 16

While Jim initially came across as a decent enough guy, it was soon revealed that Carrie broke up with him for a good reason — he's awful. Carrie repeatedly warned Miranda he was not a good guy and that they ended on bad terms. However, Miranda tried to convince Carrie that maybe he'd changed and that they should all get together.

While the three grabbed drinks, Jim began hurling digs at Carrie, saying she "walked all over him" while they were in a relationship, among other pointed insults.

As a result, Miranda swiftly ended things with him.

Kurt Harrington was described as the "loathe of [Carrie's] life."

sex and the city kurt harrington
Kurt Harrington. HBO

Appeared in: Season 1, episode 1

Carrie slept with Kurt Harrington in the first episode of the series to prove that women can "have sex like men" without emotional attachment. It's clear they'd been sleeping together on and off for years, but no relationship had ever formed.

He doesn't seem like a bad guy, he's just not boyfriend material.

Willie Applegate went on one "sim-u-date" with Carrie before she started dating Jack Berger.

willie sex and the city
Carrie Bradshaw and Willie Applegate. HBO

Appeared in: Season 6, episode 1

Aw, Willie. I'm sure he was a sweet guy, but that date couldn't have gone worse. Between the horrible pick of a date spot, knocking the table over, and going on and on about his stye, it's not surprising that he and Carrie didn't go any further than the first date.

Howie Halberstein, the best man at Harry and Charlotte's wedding, injured Carrie during a night of bad intercourse.

howie sex and the city
Howie Halberstein. HBO

Appeared in: Season 6, episode 8

Howie Halberstein initially came across as funny, charming, and good-looking. However, Carrie was only looking for a "fling" while he was in town for Harry and Charlotte's wedding, and he apparently was looking for more.

After a night of horrible sex, causing Carrie to be hunched over in pain the next day, she told him she was just looking for a bit of fun. He completely lost his head, drunkenly called her a b---- in his best man's speech, and said she "used him for sex" in front of everyone at the wedding.

Wade Adams owned a comic book store on St. Mark's and lived with his parents.

wade adams sex and the city
Wade Adams. HBO

Appeared in: Season 3, episode 15

Wade made Carrie feel like she was in high school again, between his old Styx albums and his affinity for a Razor scooter. However, he was also completely immature. He put the blame on Carrie when they were caught smoking weed in his parents' apartment — after which, we never saw him again.

"Twenty-something" Sam had perhaps the most disgusting apartment imaginable - and in New York City, that's saying something.

sam sex and the city
Sam. HBO

Appeared in: Season 1, episode 4

Sam was just your average 20-something-year-old guy with a tongue ring who didn't have a clue. His apartment was littered with garbage, pizza boxes, and other gross knick-knacks. He also didn't have coffee filters or toilet paper, which is simply unacceptable.

While he was a good kisser and always up for a night out on the town, he definitely wasn't mature enough for a woman like Carrie Bradshaw.

Jeremiah, a performance-artist-turned-cater-waiter, showed Carrie a nefariously placed tattoo while she was at a party with Mr. Big.

jeremiah sex and the city
Jeremiah. HBO

Appeared in: Season 2, episode 10

Carrie told Mr. Big she loved him but didn't get a real response for days. One night, she was snubbed by Mr. Big at a stuffy Upper East Side party where no brown food or drink was allowed. She then ran into Jeremiah, with whom she said she had "engaged in a mild flirtation for years," out on the balcony.

Angry and a little heartbroken, Carrie slept with Jeremiah. Mr. Big called the next day to tell her he did love her, he just needed to do things in his own time — while she was still in bed with Jeremiah.

Carrie reasoned with herself that it's not cheating until both parties say "I love you," but we really think that Jeremiah was just a distraction from her true feelings for Mr. Big.

Seth, played by Jon Bon Jovi, met Carrie in their therapist's waiting room.

seth jon bon jovi sex and the city
Seth, played by Jon Bon Jovi. HBO

Appeared in: Season 2, episode 13

After meeting in their therapists' waiting room, Carrie ended up dating and sleeping with Seth. He revealed to her that he's in therapy because he completely loses interest in the women he dates after sleeping with them. Horrified, Carrie said she's in therapy because she picks the wrong men to be with.

Whatever his issues are, that seems like information Seth should have revealed before sleeping with Carrie.

Jake, played by a young Bradley Cooper, barely had a storyline, other than that he was young and hot.

bradley cooper jake sex and the city
Jake, played by Bradley Cooper. HBO

Appeared in: Season 2, episode 4

However, when you're Bradley Cooper, you don't need much else. I only wish we had gotten more than just a few scenes.

Ray King owned a jazz club and wouldn't let us ever forget it.

ray king sex and the city
Ray King. HBO

Appeared in: Season 4, episodes 3 and 4

Ray King, aptly nicknamed Pork Pie by Mr. Big, was overall a ridiculous character. Despite being the best in bed that Carrie's ever had, she broke up with him after realizing he had ADHD and was unable to hold a conversation with her.

While that's undeniably problematic and stigmatizing — "Sex and the City" isn't without its problems — the bigger issue was that Ray's entire personality centered around his obsession with jazz. It's shocking that he was in more than one episode.

John McFadden, Carrie's "f--- buddy," was a decent guy but was clearly too vanilla for Carrie to consider actually dating him.

john mcfadden sex and the city
John McFadden. HBO

Appeared in: Season 2, episode 14

John and Carrie's relationship was obviously purely physical, despite Carrie trying to make it into something more. He offered Carrie free phone minutes as a gift on the date and had nothing to say when she was talking about how lucky she felt to live in New York.

Overall, he's not a bad guy — he's just clearly not on Carrie's emotional or intellectual level.

Patrick Casey was a recovering alcoholic who ended up getting addicted to Carrie.

patrick casey sex and the city
Patrick Casey. HBO

Appeared in: Season 2, episode 16

Patrick Casey and Carrie met on the street and immediately got off to a rough start. He told her he was in Alcoholics Anonymous and that his sponsor had told him not to date anyone until he'd been sober for a full year. However, they began dating anyway.

Carrie soon realized that Patrick had become addicted to having sex, which he'd never done without alcohol. After Carrie said she wanted to take a break from their relationship, he relapsed and stripped in the street outside her apartment, calling out her name in the middle of the night. He's not a bad guy, but he clearly wasn't ready to enter a relationship.

Paul Denai was a famous fashion photographer who couldn't refrain from snapping photos of Carrie, even after she fell on the runway during a fashion show.

paul sex and the city
Paul Denai. HBO

Appeared in: Season 4, episode 2

Carrie and Paul engaged in a mild flirtation throughout the episode after she revealed she was a huge fan of his fashion photography. They drank wine and looked through his photos while he piled on the compliments.

However, after Carrie tripped on the runway while walking in a fashion show, he took photos of her during the embarrassing incident. If it were us, we'd never speak to this guy ever again either.

Keith Travers, played by Vince Vaughn, pretended to be a big-time Hollywood agent to woo Carrie but was actually just Carrie Fisher's assistant.

keith travers sex and the city
Keith Travers, played by Vince Vaughn. HBO

Appeared in: Season 3, episode 14

Despite being played by the tall and attractive actor Vince Vaughn, Keith Travers was no catch. While visiting Los Angeles, Carrie and Travers met at a Hollywood premiere after-party. He lied to Carrie about his job, his income, and his entire life.

At the end of the episode, they were caught in bed at actress Carrie Fisher's house, which Travers had claimed to be his own. Carrie left in a hurry and never saw him again.

Jack Berger was the definition of an insecure man-child and broke up with Carrie on a Post-it note.

jack berger sex and the city
Jack Berger. HBO

Appeared in: Season 5, episode 5, 8; season 6, episodes 1-6

Jack Berger had a lot of things going for him. He had a good sense of humor, possessed boyish good looks, and was a writer, just like Carrie. However, he was also passive-aggressive, insecure, had issues with his ex-girlfriend, and was extremely jealous of Carrie's success.

He also broke up with her in perhaps the worst way possible, on a Post-it note, with three sentences: "I'm sorry. I can't. Don't hate me."

Speaking for "Sex and the City" fans everywhere, we do hate you, Berger.

Bill Kelley, a politician, shamed Carrie for being a sex columnist but had his own kinks behind closed doors.

bill kelly sex and the city
Bill Kelley. HBO

Appeared in: Season 3, episodes 1 and 2

Carrie's relationship with city comptroller candidate Bill Kelley was promising at first. He persistently pursued her after her "bad breakup" with Mr. Big in the first season, and he quickly included her in his life. She became the perfect politician's girlfriend, sporting vintage Halston and attending campaign events.

However, their relationship hit the rocks after he asked her to indulge an out-of-the-box sexual preference. She declined, and he later shamed her for being a sex columnist, saying it was bad for his career. They not so shockingly broke up.

Gilles, a visiting French architect, wined and dined Carrie for a few days before leaving her $1,000 on his nightstand.

gilles sex and the city
Gilles. HBO

Appeared in: Season 1, episode 5

Gilles was handsome, charming, successful, and had an endearing French accent. After spending a wonderfully romantic weekend with Carrie, he left her an envelope filled with money after they slept together the night before his departure from New York.

Carrie, rightfully so, was offended, but it's possible he just wanted to help her out financially — she did complain about not making much money — and thank her for a nice time.

Dr. Bradley Meego was "good on paper," but really, really boring.

dr meego sex and the city
Dr. Bradley Meego. HBO

Appeared in: Season 2, episode 17

Carrie met Dr. Bradley Meego while attending a book party in the city. The meet-cute soon turned into a Hamptons summer romance, but Carrie wasn't sure if she actually liked him or if he was just "good on paper."

Carrie inevitably forgot all about Dr. Meego after running into Mr. Big and his new girlfriend, Natasha, after they returned from Paris. That's a great way to sum up Meego as a whole: completely forgettable.

Sean, "the marrying guy," was keen to tie Carrie down.

sean sex and the city
Carrie Bradshaw and Sean. HBO

Appeared in: Season 1, episode 3

Sean and Carrie went on a few nice dates after being set up by mutual friends. He then invited her, Miranda, and Samantha to a housewarming party at his beautiful new apartment. Carrie inevitably realized that he was eager to find a wife but that she didn't see a future with him, despite him being every single woman's dream.

Carrie set him up with Charlotte, who was also anxious to get married, but they also broke up after realizing they had different tastes in place settings.

Vaughn Wysel had an incredible family, but he also had problems in the bedroom.

vaughn sex and the city
Carrie Bradshaw and Vaughn Wysel. HBO

Appeared in: Season 2, episode 15

The successful short-story writer seemed perfect for Carrie. He was smart, cute, and had a wonderful family helmed by his mother, played by "The Mary Tyler Moore Show" actress Valerie Harper. However, he also had problems in the bedroom that led to the demise of his and Carrie's relationship.

In the end, Carrie realized she had a better connection with his mother than she ever did with him. However, aside from his shortcomings, he was a put-together guy with a lot going for him.

Jeremy was Carrie's high school boyfriend who ended up checking himself into a psychiatric facility.

jeremy sex and the city
Jeremy. HBO

Appeared in: Season 6, episode 10

Jeremy was all the things a good boyfriend should be. He was funny, kind, romantic, and he and Carrie shared an adorable history. However, the two ended up parting ways after he revealed he had checked himself into a psychiatric facility in Connecticut.

While they tried to continue dating — Carrie even visited him at the center at one point — they both knew they couldn't make it work long-term. Some good things are simply better off left in the past.

Sean was a younger, bisexual guy whom Carrie dated briefly.

sean sex and the city
Sean. HBO

Appeared in: Season 3, episode 4

Carrie repeatedly pestered Sean about whether he was attracted to men or women more and cringingly asked if she "kissed better than a guy." Carrie ended up leaving him at a party after a game of all-gendered spin the bottle, where she described herself as an "old fart."

Honestly, Sean deserved someone who would both validate and support his sexuality, not shame it.

Joe Stark, "the new Yankee," was nice, successful, and really good-looking.

joe sex and the city
Joe Stark. HBO

Appeared in: Season 2, episode 1

As the first love interest introduced in the second season, "new Yankee" Joe Stark certainly came out swinging. He and Carrie immediately hit it off, and they even ended up on Page Six together.

However, despite him being the perfect rebound guy, Carrie broke it off after she realized she still had feelings for Mr. Big. We're sure whoever Stark ended up with was a lucky girl, indeed.

Louis Leroy was a charming, handsome Navy sailor who Carrie met during New York City's Fleet Week. She broke up with him after he dissed the city.

louis leroy sex and the city
Louis Leroy. HBO

Appeared in: Season 5, episode 1

Louis Leroy was a short-lived fling of Carrie's but certainly made an impression in our minds. He was a simple guy with simple tastes and didn't enjoy the "garbage" and "noise" of New York City.

While that may have been a deal-breaker for Carrie, his winning smile, Navy uniform, and Louisiana accent were undeniably swoon-worthy.

Ben, the one normal guy Carrie dated after a series of bad dates in the first season, broke up with her after she ransacked his apartment looking for something freaky.

ben sex and the city
Ben. HBO

Appeared in: Season 2, episode 3

One of the few guys in the series who actually broke up with Carrie first, Ben was the editor of a "hip political magazine" who seemed to really like her — that is, before she tore his apartment apart looking for evidence that he was secretly weird.

While he was only featured in one episode, we can't help but think this was a missed opportunity for Carrie to be with someone really great.

Aleksandr Petrovsky was smart and successful, but he also never allowed Carrie to be her true self.

aleksandr petrovsky sex and the city
Aleksandr Petrovsky. HBO

Appeared in: Season 6, episode 12-20

Carrie's entire relationship with Aleksandr Petrovsky seemed like something out of a romance novel — up until the moment she realized she had changed every part of herself to fit into his world.

After abandoning her friends and career in New York City, Carrie moved to Paris to be with Petrovsky, an acclaimed artist. However, she soon realized that he wasn't her one true love after finding herself constantly alone and wondering what it would have been like to be in the city of lights with her old flame, Mr. Big.

He ranks high on this list because of the length of their relationship, but Petrovsky is a widely debated character in the "Sex and the City" universe. Many argue he was too old for Carrie, while some say he was worldly, sophisticated, and mature. In our opinion, his cynicism and cold personality were just totally wrong for Carrie, who is a fun-loving romantic at heart.

Mr. Big - love him or hate him - is Carrie's soul mate. However, he's also emotionally unavailable throughout most of the series.

mr big
Mr. Big. HBO

Appeared in: Seasons 1-6

Carrie and Mr. Big were arguably destined to be together from the very first episode. Despite all the breakups, drama, scandals, and fights, they finally ended up together at the end of the series.

Mr. Big had a lot to be criticized for. He was emotionally unavailable, manipulative at times, and didn't give Carrie what she truly wanted or needed until the finale of the series.

However, he was also undeniably charming with his goofy sense of humor and the endearing banter he and Carrie shared in practically every scene they had together. At the root of it all, Carrie and Mr. Big were friends — the cornerstone of any good relationship. Love him or hate him, Carrie ended up with the right guy for her.

Aidan Shaw was by far the sweetest guy Carrie dated throughout the show.

aidan shaw sex and the city
Aidan Shaw. HBO

Appeared in: Seasons 3-6

Mr. Big might have been the right guy for Carrie, but Aidan was the perfect guy, period. Introduced in the third season as an all-American furniture designer with an adorable dog and floppy hair, Aidan was immediately portrayed as the antithesis of aloof businessman Mr. Big.

Aidan was warm, loving, and ready for a serious commitment. However, this proved to be the downfall of his relationship with Carrie throughout the series. After she had an affair with Mr. Big the first time she and Aidan dated, they got back together only to break up again when she admitted she wasn't ready to marry him.

Aidan's storyline was both heartbreaking and swoon-worthy for many "Sex and the City" fans, and many still insist she should have ended up with him. However, it wasn't written in the stars, and he went on to start a family with another furniture designer. If that isn't totally adorable, we don't know what is.

Read the original article on Insider