All of the Sex and the City Boyfriends, Ranked

The very first episode of Sex and the City premiered 20 years ago next month. To mark this auspicious anniversary, ELLE.com is celebrating some of its most ridiculous, memorable and controversial moments—from the fashion to the flings.

Perhaps no show on television has more exhaustively documented the habits, characteristics and shortcomings of the modern-day boyfriend than Sex and the City. Even though it’s been off the air for more than a decade, it’s tough to think of a pre-Tinder guy problem that the show didn’t tackle—from erectile dysfunction (see: Trey) to emotional dysfunction (see: honestly, most of them).

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Of the 100+ men the ladies dated or boffed over the course of six seasons, only 45 made it beyond the first-date hurdle. We’re rating them here. They’re a largely disappointing bunch, with their most common characteristic being an uncanny ability to ignore all criticism from their girlfriends.

Welcome to the wide world of penile issues and personality disorders, where we find the boyfriends of Sex and the City.

45. Ned: Season 2, Episode 5

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Charlotte met Ned while he was performatively mourning his dead wife in a cemetery. Charlotte was impressed that he’d been married before, and even more impressed that he didn’t still have an ex hanging around to make her feel weird. But it turned out he was treating his wife’s grave like a Bumble account: His grave visits were just a way to get women to hit on him. It doesn’t get much lower than that, which earns Ned the bottom spot on our list.

44. Jack: Season 2, Episode 12

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Jack likes public sex. He is up front with Miranda about his kink, and she starts getting into it herself. But then, he tricks her into having loud sex with him while his parents are nearby in the apartment. As if that weren’t bad enough, his parents walk into the room—and even that doesn’t stop him. He keeps it up until the very end, as his parents stand in the doorway of his room and watch him finish inside Miranda. Horrifying.

43. Jim: Season 3, Episode 16

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Jim is Carrie’s ex, but he pops up again to court Miranda. Any guy who’s overly eager to dip into the same friend pool twice deserves a little extra scrutiny, but his lingering hatred for Carrie really seals his demise. At a three-way lunch date intended to smooth over any awkwardness, he flips out and calls Carrie an asshole. Miranda promptly dumps him, and like a true prize, he says, “Ooh, the fancy lawyer lady’s breaking up with me, like I give a shit.” Totally emotionally abusive and sociopathic. How did he get Miranda or Carrie to even look at him in the first place?

42. Jack: Season 1, Episode 8

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Shortly after Jack (yes, another Jack, he’s one of at least three) and Charlotte make it official, he suggests a threesome. It seems a little early for that, but according to the episode, “threesomes are the blow jobs of the ’90s,” so whatever. Jack successfully maneuvers both Charlotte and a woman they’ve just met into bed with him—and then he completely ignores Charlotte. That’s rude behavior from any sexual partner, let alone one who’s your boyfriend. As Samantha says in this episode, “The only way to do a threesome is to be the guest star.” Truly wise words.

41. Aaron: Season 2, Episode 2

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Aaron wanted Miranda to participate in his dirty talking kink—but only on his terms. When Miranda finally gets into it and dares to say out loud that he liked a finger in his ass, Aaron freaks out and we never hear of him again.

40. Kevin: Season 1, Episode 11

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Charlotte is disappointed that Kevin can’t fully function sexually because he takes Prozac. He seems fine with an orgasm-free life, but Charlotte’s not—and either way, it’s bad boyfriend behavior not to share this with someone before you start sleeping together.

39. Brad: Season 3, Episode 5

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Charlotte dates Brad but has to dump him when he turns out to be irredeemably bad in the kissing department. Gross, but maybe for a fellow sloppy kisser, he’d be the best boyfriend around.

38. Michael Conway: Season 1, Episode 7

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Michael and Charlotte made things official real quick. Then he announced that if she wouldn’t give him blow jobs, he’d find them somewhere else. It’s not the blow job preference that makes Michael a bad boyfriend—it’s the loathsome pushing-Charlotte’s-head-down move and the threat that he’d cheat on her within days of their becoming boyfriend and girlfriend. Can you even imagine?!

37. Vaughn Wysel: Season 2, Episodes 15 and 16

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Played by Justin Theroux, Vaughn’s character has a creepy vibe and a major issue with premature ejaculation. Carrie hangs in there with this dud because of his cool mom, played by Valerie Harper. There’s nothing wrong with prematurely ejaculating, but Vaughn seemed totally unwilling to admit he had a sexual problem, like so many of the other men on this list.

36: Roger Cobb: Season 2, Episode 15

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Roger Cobb gets way too much sympathy from the SATC-watching public. Sure, he’s a caring dad, but he introduces his kid to Miranda way too early. It’s weird. Plus, he seriously needs to re-examine his stance on banging while his son’s home. One morning, Roger’s son barges in on a naked, post-coital Miranda. She slams the door on the kid, accidentally hurting him, and he starts wailing. Of course his dad takes his side, kicking Miranda to the curb in the process. But it’s not Miranda’s fault someone else’s kid almost walked in on her naked. Roger should have foreseen the potential for a traumatic post-sex run-in between his kid and his girlfriend, and taken preventative measures.

35. Don: Season 2, Episode 13

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Don seemed like a gregarious and fun guy, but he couldn’t have sex with Samantha unless his favorite sports team won. I’m sorry, what?! We’ve all met guys who can only express emotion through sports fandom, but this is ridiculous. He didn’t seem like Samantha’s type, anyway.

34. Ted: Season 1, Episode 6

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Ted and Miranda are getting serious fast, but then she ransacks his apartment and finds spanking porn. To gauge his actual interest in spanking, she brings it up in passing after a date. He freaks out, ghosts her, and switches gyms so that he never has to see her again. If Ted’s really that ashamed of his own kink, then he’s got some serious issues and it’s good that he bounced.

33. Josh: Season 2, Episode 4

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During a squad-wide moment of desperation after Carrie’s thirty-shaming “Single and Fabulous?” magazine cover, Miranda tries to force a relationship with Josh. He can’t make her orgasm, and when she tells him she’s been faking it, he assumes she has “like a physical problem or something.” Despite this, she agrees to tutor Josh. But when hours of lessons don’t do the trick, she fakes it one last time and then ghosts him.

32. Arthur: Season 3, Episode 1

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Arthur was another of Charlotte’s strong-jawed WASPs with a major flaw: He loved punching people in the face over tiny infractions. Charlotte wisely skedaddles after he reveals his penchant for assaulting strangers: Violence is never the solution, especially not when the problem is as small as a waiter informing your date that he can’t alter the menu.

31. Bram Walker: Season 2, Episode 16

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Bram is the guy who falls asleep having sex with Charlotte. In the canon of bizarre things men can surprise you with during sex, sleep is definitely one of the better options. Still, that doesn’t make it okay. Bram clearly needs to take care of himself before he can take care of anyone else.

30. Alexander Lindley: Season 3, Episode 6

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Alexander Lindley is the boyfriend whose orgasmic refrain of “you fucking bitch, you fucking whore” you can probably still hear in your head. He was unable to stop insulting Charlotte every time he came. When Charlotte spoke up, he acted like it was NBD. Charlotte hung in there way longer than this dude deserved.

29. Thomas John Anderson: Season 1, Episode 12

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Thomas John Anderson is a playwright Miranda dates, who has to shower after sex. Like, immediately after sex, every single time, apparently because he’s Catholic (Sex and the City always was so culturally sensitive). When Miranda presses him on the shower thing, he flips out and issues a monologue that later makes it into one of his plays. He needs more help than any girlfriend can give him, and should at least stop dating until he can figure out a way not to make the women he sleeps with feel dirty. But perhaps more pressing is this: What did this angsty whiner really bring to the table in the first place?

28. Ethan Watson: Season 2, Episode 6

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Ethan Watson was Miranda’s boyfriend who needed porn to get in the mood. So do a lot of people, right? Well, this was back when people watched porn on VHS and DVD. Imagine how much effort it required to become a porn addict back then! Look, there’s nothing wrong with liking porn, but Ethan had an unhealthy relationship with it and, more importantly, ignored the fact that his girlfriend wasn’t down. Next.

27. Doug: Season 4, Episode 3

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Doug is played by the comic Jim Gaffigan. He seems sweet, but after just a few weeks of dating, he decides he’s comfortable enough with Miranda to literally poop in front of her while she’s in the bathroom. Not only is this completely disgusting, it also reveals some potential issues around boundaries. While there might be a lady out there who’s craving a free and wild pooper like Doug, dropping a deuce in front of your new partner is objectively bad boyfriend behavior, sorry.

26. Justin Anderson III: Season 5, Episode 5

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In Charlotte’s haste to find an impressive rebound plus-one for Carrie’s book launch, she apparently forgets to tell Justin Anderson III that she’s still married. Before he knows it, he wakes up in Char’s apartment as Bunny, her mother-in-law, drops by for some quick slut-shaming. When he finds out Charlotte’s actually separated and not divorced, he scowls and walks away, and we never hear from him again. While you have to sympathize with Charlotte for wanting to bring a perfect date to Carrie’s party mid-divorce, you can’t blame Justin for getting the hell out of that mess.

25. Adam Ball: Season 3, Episode 9

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You’ll remember the ridiculously named Adam Ball as the guy with the funkiest-tasting spunk. Samantha tries feeding him wheatgrass shots and a ginger melon smoothie to cure his affliction, but it doesn’t work. When she breaks the news to him, he calls her “one of them two-blow-job chicks.” Gross. Sam asks him to drink his own semen so that he’ll know how it tastes. Despite fears that this might be “gay” of him, he does it, but he lies and says he’s “fine with” the taste. Samantha shrugs and goes down on him. We never see him again on SATC, so it’s safe to say that was his last beej from Sam.

24. Bill Kelley: Season 3, Episode 1

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City comptroller candidate Bill Kelley is a huge disappointment. He seems like Carrie’s perfect match in the witty banter department—and the politician-plus-sex-columnist pairing is just so New York. But after he asks her to pee on him and she demurs like the kinkless sex expert she is, he dumps her. This wouldn’t be the biggest deal, but he pretends it’s because her career as a sex columnist is too “seamy” and could cost him the election. Some guys just want a woman who’s totally sweet and innocent, except when it comes to his very specific kinks.

23. Kurt Harrington: Season 1, Episode 1

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Kurt’s introduced in the pilot as Carrie’s ex, referred to by Stanford as the “love of [her] life.” She calls him a mistake—and then asks him out on a date in the name of “research.” Okay, girl. She tries to “have sex like a man” with him (read: without commitment or feelings). It works, and Kurt tells her he’s totally cool with this arrangement. This leaves Carrie thrown. She apparently thought he’d fall in love with her after she withheld a single blow job. Kurt’s painted as a player, but all he did was agree to some casual sex. Carrie’s actions are way more bizarre. The red flags in this storyline come from her, not Kurt.

22. Brian: Season 1, Episode 4

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Brian has Charlotte’s big three: “Looks, manners, money.” But he also has a hankering for booty sex, and Char’s just not down. This leads to a memorable group meltdown in the back of a cab. Charlotte decides she can’t be “Mrs. Up the Butt,” and Brian is never heard from again. Sucks for Charlotte, but hey, the heart wants what the heart wants.

21. Chivon Williams: Season 3, Episode 5

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Chivon is at the center of a rather problematic storyline which culminates in Samantha yelling at his sister in a club, “Get your big black ass out of my face.” Yikes. Chivon himself is hot and nice, but also let his sister meddle in his dating life. Still, it’s for the best that this relationship didn’t work out, since Samantha has issues she needs to work on.

20. Stephan: Season 2, Episode 11

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Charlotte’s boyfriend Stephan opens the definitely not politically correct debate: can a guy who “seems” gay be straight? Stephan himself says yes: “I’m a 35-year-old pastry chef who lives in Chelsea,” he tells Charlotte. “If I were gay, I’d be gay.” Charlotte attests that he seems super straight in bed, and that might be enough for her. But when he flips out over a mouse in his kitchen, she decides she can’t deal with a relationship where neither party has an evolved “masculine side.” Another very yikes SATC moment.

19. Wade: Season 3, Episode 15

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Carrie meets Wade, alias Power Lad, in a comic book shop. He lives at home with his parents, which is a red flag, but Carrie goes along with it. He also considers staying in with fried chicken and weed to be a date—which is subpar for Ms. Bradshaw’s standards. (Although, for today’s post-recession, student-debt-laden NYC daters, it might be considered a pretty typical second or third date.) Their fling ends when Wade’s mom catches them smoking, and Wade blames it on Carrie. She retaliates by taking the Mary J with her when she leaves. Everything happens for a reason!

18. Mike: Season 2, Episode 9

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Poor, uncircumcised Mike definitely deserved better than what the SATC gods had in store for him. After dating for just a short while, Charlotte persuaded Mike to undergo circumcision surgery. Why? Because Charlotte was weirded out by his foreskin. It’s bizarre that this storyline and Charlotte’s request were treated as normal. If the genders were reversed on this, the gals would’ve been rightfully outraged that a guy suggested surgery to “fix” a woman’s perfectly functional genitals. But Mike got the surgery and experienced a newfound burst of bachelor confidence that Charlotte couldn’t abide. Pour one out for Mike, who should’ve just found himself a girlfriend who was used to uncut men. At least his storyline resulted in one of the best SATC episode names: “Old Dogs, New Dicks.”

17. Jack Berger: Season 5, Episode 5 and beyond

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Jack Berger has to be the most universally reviled Carrie boyfriend. He starts out so promising: witty, creative, capable of rocking a leather jacket. But he’s also not fully over his ex—and he begins to resent Carrie for her success. Berger needs to date a doormat, or at least a super non-threatening kindergarten teacher. So while, yes, he’s charming, he has some major, major issues. Who gets mad at a gift from Prada?! And let’s not even get started on the Post-It…

16. Ray King: Season 4, Episodes 3 and 4

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Carrie starts seeing jazz musician Ray during a deranged attempt to be “just friends” with Big. The sex is great, and the flirting in front of Big is even better. But whenever Carrie gets Ray alone for too long, she realizes she can’t truly connect with him because of his frenetic personality. He’s not a bad guy, but maybe some a meditation app would help?

15. Harvey Terkell: Season 2, Episode 10

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Another one to file under “storylines that would never happen in 2018.” Samantha is creeped out by her BF Harvey’s relationship with his Thai housekeeper, Sum. Sum is repeatedly referred to as a “servant” and we’re supposed to be creeped out when Harvey says, “Isn’t she the best?” It’s all over for Harvey when he takes Sum’s side after she claims Samantha hit her. What, was he supposed to fire his employee on the spot for claiming she’d been assaulted?! We can’t give Harvey a low boyfriend rating just because he took his housekeeper’s side in a spat. Sorry.

14. Skipper Johnston: Season 1, Episode 1 and beyond

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Skipper Johnston was too pure for the SATC world. “He’s like a sweet little seal pup,” Carrie declares in one ep, with Miranda retorting, “That you sometimes want to club.” With his Shirley Temple-esque ringlets, whiny voice, horrible style, and too-cherubic face, it’s a wonder Miranda manages to get it up for Skipper at all. Yet somehow, he bats above his league time and time again. Remember the hottie he dumps mid-sex when Miranda calls him? As far as boyfriends go, he’s honestly too boring and wishy-washy. In fact, Skipper might be the male version of the doormat Jack Berger’s looking for.

13. The New Yankee: Season 2, episode 1

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The New Yankee is the rebound boyfriend dreams are made of. After the first of many Big and Carrie breakups, Carrie seeks revenge by publicly squiring this young, hot rookie around town. He’s even part of Big’s favorite sports team. It’s like he was engineered in a lab to make Carrie’s ex jealous. The only issue: Like so many other young hot rebounds, he doesn’t bring a ton to the table in the personality department. Still, he fulfills his revenge duties and then some.

12. Trey MacDougal: Season 3, episode 7

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When you look at how Charlotte’s exes sexually tormented her, it’s no surprise she subconsciously sought out a guy who couldn’t get it up. Trey is like a cyborg cooked up in Charlotte’s wildest dreams, with a penis problem that she never checked up on until it was too late. Charlotte decides to roll the dice and marry Trey without ever having slept with him, and it turns out to be a horrible mistake. There’s nothing wrong with erectile dysfunction, provided you’re up-front about it and willing to work through solutions with your partner. Trey was neither. Plus, he refused to stand up to his bonkers mom. Trey proves that if your bae is unwilling to solve or even acknowledge problems, money and pedigree can’t do it for him.

11. James: Season 1, Episode 12 and beyond

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Samantha dumps James because of his tiny (“three inches,” she wails) manhood. Now, let’s be clear: The conversation around sex and pleasure has shifted, and we no longer prize P-in-V sex as the heterosexual holy grail the way we did 20 years ago. However, James is a bland enough character that when Samantha says she can’t deal, no one’s sad to see him go.

10. Sean: Season 3, episode 4

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Sean was adorable, but clearly too open-minded for Carrie. He was openly bisexual and she couldn’t handle it. Can you imagine a sex columnist being squicked out by bisexuality in this day and age? Not cool, Carrie. But as we’d go on to learn, despite Carrie’s penchant for gabbing about sex, she needed a plain vanilla fuddy-duddy like Big or Petrovsky.

9. Tom: Season 5, episode 4

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Tom didn’t get a fair shake! He and Miranda meet at Weight Watchers and bond over Krispy Kreme donuts. But when he goes down on her, Miranda’s grossed out by his inability to emerge with more than, as Samantha put it, “a fine lip gloss.” This is too much for Miranda to handle, and it yields the most unforgettable/unforgivable Carrie pun: “Miranda went out with an overeater and he overate her.” Tom can’t take the criticism over something eating-related, so they part ways. Hopefully Tom has since found a woman who appreciates his appetites in and out of the bedroom.

8. Aleksandr Petrovsky: Season 6, Episode 12 and beyond

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The best thing you can say about Aleksandr “You are comic?” Petrovsky is that he paid for Carrie to move to Paris for a hot minute, and what could be bad about that? Simply put, the Russian is a utility boyfriend: a guy you honestly don’t even like that much, and who your friends downright hate, but who you need to date in order to grow in your life. Utility boyfriends like the Russian often coincide with a big move or a major life change. After it’s all over with, you’ll be like, “LOL what was I thinking? Did I really pretend to enjoy a carriage ride in a blizzard through Central Park for that guy?” but you will have come out the other end a better, more developed person.

7. Mr. Big: Season 1, Episode 1 and beyond

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Samantha refers to Mr. Big as the “next Donald Trump” in the pilot. In 1998 when the show premiered, that just meant “guy with flashy tendencies who makes bank on real estate.” In 2018, it means “deluded narcissist who is pathologically unable to empathize with other humans.” These are both pretty apt descriptions of Mr. Big, né John James Preston. Big is a commitment-phobic borderline sociopath who is so self-absorbed that in the movie version of SATC, he leaves Carrie at the altar because she won’t answer her cell phone. He has no qualms about hiding his past marriage from Carrie, refuses to introduce her to his mom and later cheats with her after he marries someone half his age. He’s an emotional eighth-grader. Still, we’re supposed to like him at the end of the series. His final redemption comes when he jets all the way to Paris to rescue Carrie from the clutches of half-man-half-squirrel Aleksandr Petrovsky. But for someone as wealthy as Big, flying to Paris is only slightly less convenient than Ubering to Bushwick. Big takes an opportunity to save the day and rescue Carrie not because he’s selflessly in love with her, but because he selfishly wants to get her back and he knows he needs a grand, heroic gesture to do it. The only reason Mr. Big ranks as high as he does on this list is because while he may be the worst, he’s in fact Carrie’s perfect match.

6. Richard Wright: Season 4, Episode 10

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Who doesn’t have a soft spot for Richard Wright despite his dastardly behavior? Richard was a hotel-owning dynamo with a certain je-ne-sais-quoi that almost made you want to overlook his philandering. Yes, the ranking he’s getting here is way too high for a cheater, and that doggy-style hotel party sex scene between Samantha and him was mighty uncomfy. But still. He served his purpose at the time. I feel like maybe in 2018, he and Sam could’ve made polyamory work. Plus, he had a rooftop pool.

5. Smith Jerrod: Season 6, Episode 2 and beyond

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Smith is a perfect 10 physically, he’s sweet and nice, he doesn’t drink or do drugs, he dates a much older woman and thinks she’s the hottest thing on the planet, and he sticks with her during chemo? Why isn’t Smith Jerrod number-one on this list, you might ask? Well, because Smith Jerrod is not real life. Sorry. I’m pretty sure he was meant to be a figment of Sam’s imagination (think about it—how often do we really see him talking to other characters?), because not even the SATC writers could come up with a character this fantastical and expect us to believe he was anything but a daydream. He lacks verisimilitude. This is a list ranking plausible boyfriends, not fanfic.

4. Steve: Season 2, Episode 8 and beyond

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Steve is a nice and supportive guy who loves Miranda, his puppy, and their child. But he has two flaws: First of all, he needed a kick in the pants to reach his full potential in life. That old apartment of his was no bueno for a man in his thirties. And secondly, he cheats on Miranda in the first SATC movie. But still, nobody’s perfect and the rest of the SATC guys are so mediocre, we’ll have to let it slide.

3. Aidan Shaw: Season 3, Episode 5 and beyond

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Poor Aidan got the roughest break out of any of the boyfriends in the show, despite being one of the good guys. The failure of Aidan and Carrie’s relationship shows us that no amount of niceness can make up for incompatibility. Aidan’s idea of a fun night in was a bucket of KFC and a movie, which made Carrie want to climb up a wall. Like so many other dudes on this list, Aidan would’ve been the best boyfriend ever—to someone besides Carrie. Also he cheats on the mother of his children in the movie, so that knocks him down a peg.

2. Robert Leeds: Season 6, Episode 9

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Robert Leeds is gorgeous, smart, charming, and successful. He’s probably the second hottest of the top five SATC boyfriends, and he’s a freaking doctor. There’s literally nothing wrong with him. I wouldn’t even consider the “I Love You” cookie to be a flaw. It was corny, sure. But if Miranda wasn’t hung up on the true love of her life Steve at the time, even her icy heart would’ve been warmed by such an adorably ham-fisted gesture. Robert Leeds got an unfair shake and I hope his life post-SATC treated him well.

1. Harry Goldenblatt: Season 5, Episode 7 and beyond

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There are three good long-term boyfriends on Sex and the City: Harry, Steve, and Aidan (as we’ve already covered, Smith was some sort of peri-menopausal mass hallucination). Harry is the best one, though—not only because he’s the funniest, but also because Steve and Aidan are tainted by infidelity in the SATC movies. Harry might not be considered the hottest by today’s excruciatingly high beauty standards, but he is a GOOD MAN who CARES ABOUT HIS FAMILY. Harry is terrible at home decor, grooming, and wardrobe, but he knows he’s terrible at these things, so he lets Charlotte take the reins. Harry’s only flaws are encapsulated in a single 22-minute episode: He goes through a phase of putting his naked butt on the furniture and leaving tea bags all over the house. But both of these problems are fixable, especially for someone as strong-willed as Charlotte, and they’re remedied over the course of a single story arc. Every girl deserves a Harry.

Molly Mulshine

Molly Mulshine is a writer and performer living in New York City by way of the Jersey Shore.