Sex And The City: 50 Of The Girls' Most Memorable Boyfriends, Ranked

Sex and the City introduced us to four female soulmates... and the many, many guys they had fun with along the way.

HBO's fun and frothy rom-com followed the love lives of Carrie, Miranda, Charlotte and Samantha as they dated and bedded dozens of men — and some of those men even stuck around for multiple episodes! Across six seasons, we witnessed every variety of the male species, from regrettable flings to full-fledged husband material... but which ones were actually worth hanging on to?

We're looking back at 50 (!) of the most memorable men in the Sex and the City ladies' lives and ranking them based on longevity, compatibility and general appeal. (We didn't include non-romantic male characters, but just know that Stanford Blatch is always number one in our hearts.) We couldn't help but wonder: Should Carrie have ended up with Aidan instead of Mr. Big? Was Steve really the right guy for Miranda? Did Trey deserve a second chance from Charlotte? And who was Samantha's perfect match? Let's get into it!

So put on your Jimmy Choos, pour yourself a Cosmo and read on to see where we ranked Sex and the City's boyfriends — and to find out which lucky guy took the top spot. Got some thoughts on our rankings? We knew you would: Hit the comments below to tell us who we ranked too high, ranked too low or should've included instead.

Yes, the famed artist played by Mikhail Baryshnikov was intellectually stimulating and worldly in an Old Europe sort of way. But he was also pompous, condescending, emotionally distant and ultimately abusive to Carrie, who he treated more like an amusing plaything than a true romantic partner. Really, he was only there to be a big enough jerk so we would root for one last reunion with Mr. Big... which we did, of course.

Charlotte's seemingly perfect beau turned out to be a straight-up sex criminal, physically pushing her head towards his crotch because he wanted oral pleasure so badly. And then when Charlotte dared to object, he promptly dumped her! Grrrr... let's just hope he's behind bars by now.

Oof. To be fair, Samantha only deigned to sleep with this ponytailed cheeseball because she thought she was going through menopause and didn't deserve any better. (And he does claim to make a mean wine spritzer.) Luckily for her, though, she did get her period — right on his expensive bed sheets — and never had to see him again.

Carrie's incredibly bitter ex-boyfriend — hey it's Nurse Jackie's Dominic Fumusa! — was aptly named, as it turns out. He claimed to have changed, and Miranda fell for it, but he showed his true colors when he sniped about Carrie and then turned venomously on Miranda when she tried to defend her friend. Yep, Carrie was right the first time.

Not only did this real estate tycoon brag to Samantha about his live-in Thai "servant" Sum (ick), but he took Sum's side when she blatantly lied about Samantha in order to get rid of her. The less said about this storyline, the better.

Samantha only slept with this sleazy gossip columnist to make Richard jealous... but did she have to stoop so low?

Oh good, Charlotte met a gallant investment banker who'll stand up for her and defend her honor! Oh no, it turns out the guy starts fistfights everywhere he goes and is probably in a court-mandated anger management class as we speak!

We love Jim Gaffigan's stand-up and all, but we just can't support Miranda dating a dude who won't even close the door while using the toilet. (And not just for number one.)

Samantha's dip in the lady pond was brief... but not brief enough for us. We're not against her trying out a same-sex relationship — it'd actually be surprising if she didn't, at some point — but her dalliance with this temperamental artist played by Sonia Braga just felt forced. (It never made sense that Samantha would commit to a woman when she'd never commit to a man.)

OK, just to play devil's advocate and defend this much-maligned guy: He and Carrie did have good banter together, right? But their ill-fated relationship encountered way too many speed bumps in the early going — it shouldn't be that hard! — which brought out a distinct lack of emotional maturity in Berger. They were already doomed before the infamous Post-it breakup... but that was probably the perfectly petty note to end things on.

Samantha may have enjoyed, um, taking a ride on this fireman's pole, but he was just too much of a Noo Yawk meathead to get serious about. Nice dance moves, though.

Brad was a sweet enough guy (and a doctor, to boot!), but he was too dorky to be a realistic match for Carrie. He didn't deserve to be tossed aside when Carrie ran into Big and his new love Natasha... but we weren't shocked, either.

Aka the guy whose family — including mom Valerie Harper! — was much better than he was. He was a fiction writer (and had a real Justin Theroux vibe going on), but his premature arrivals in the bedroom ensured that Carrie would have to keep looking.

Another familiar face, another unfortunate sexual situation. Future Royal Pains star Mark Feuerstein played an ex of Miranda's who was so hopeless in bed, she always had to fake it. She gave him another chance, for some reason — but even after a bunch of practice, he still couldn't finish the job! This is why the phrase "cut your losses" was invented.

Carrie's "f—k buddy" (played by 30 Rock's Dean Winters) was kind of the anti-Berger: hot and heavy in the bedroom, but a dud everywhere else. Carrie tried to turn him into boyfriend material, but it was no use. Some buddies are only good for one thing, it seems. At least he didn't try to sell her a beeper.

This guy was actually one of Samantha's longer-running relationships (three whole episodes!), and he certainly treated her well — aside from the fact that his package was, well, lacking. This one never really computed: Why would Samantha Jones, sex goddess, tolerate an unsatisfying sexual partner? She wouldn't... for more than three episodes.

Charlotte's twentysomething Hamptons fling was cute and all — hey, that's future Hell on Wheels star Anson Mount! — but he did give her crabs... and then tried to blame it on her! This is Charlotte Freaking York you're talking to here, buster!

Some classic Samantha wordplay here, and we appreciate the pre-Fleabag vibes of her forbidden pursuit of this chaste man of God. But unlike Fleabag's Hot Priest, his faith never faltered — and a man that Samantha can't get into bed doesn't have a prayer.

On the plus side, this fleeting love interest of Carrie's was an artist, and a cute one at that. (Oh hi, a pre-Suits Gabriel Macht!) But he was also obsessed with bedding models... and videotaping his conquests, often without their knowledge or consent. Yeah, pretty sure that's not entirely legal, dude.

We love us some Will Arnett, so maybe we're too forgiving of this brief flame of Miranda's. (Hey, he reads historical biographies!) But yes, he was a little too into having sex in public places — including in front of his parents. Yuck.

It's tempting to think Charlotte should've given "Mr. Pussy" more of a shot, since women around the city raved about his masterful oral skills. But he had absolutely zero to offer outside of that, and he was kind of a creep. (Did he even say one word the entire episode?) Best to let him spread his magic elsewhere.

Or, as you probably know him, Mr. Funky Spunk. We always enjoy a Bobby Cannavale sighting, but something about his pairing with Samantha just left a bad taste in our mouths.

For shame, Clark Gregg! Pretending to be a doctor just so you could sleep with Miranda... who, to be fair, was pretending to be a flight attendant at the time. When she found out he was actually just an assistant manager of an Athlete's Foot, she swiftly gave him the boot.

For a while there, it looked like Carrie had stumbled upon a quality man during her L.A. vacation — and Vince Vaughn can be quite the charmer. Keith didn't really "represent Matt Damon," as he claimed, though. He was actually a personal assistant to celebs like Carrie Fisher. But everyone in L.A. exaggerates a little, right?

This hot young thing showed up just when Carrie really needed an ego boost — he even lit her cigarette! — and he was played by a young Bradley Cooper, in his first on-screen credit. But he blew it by pointing out Carrie's face on that horribly unflattering New York Magazine cover, and vanished as soon as he appeared. Guess Alias was calling.

In one of Sex and the City's more sexually regressive moments, Carrie dumped her much younger boyfriend — played by Eddie Cahill, who made a career out of playing "the much younger boyfriend" — because he dared to admit that he was (gasp!) bisexual. Considering the age difference, the coupling probably wouldn't have worked out anyway, but Carrie and her painfully narrow view of the sexuality spectrum were to blame here, not him.

Samantha's yoga instructor was bikram-level hot, and he did try to teach her a few things about the power of conserving one's sexual energy, since he practiced Tantric celibacy. But we've heard this story before: If a guy says "no" to sex, it's a big old "no" from Samantha Jones.

This comic book store owner was a much more appealing version of The Simpsons' Comic Book Guy: dorky on the inside, but hunky on the outside. Plus, he had an incredible apartment — and a solid weed hookup! Alas, that incredible apartment belonged to Wade's parents, and once he tried to pin his weed stash on Carrie to save face in front of his mom, he turned from superhero to weakling pretty quick.

Here, Samantha ran into what we'd think she'd consider a good problem: a handsome, successful man who's too well-endowed. (A nice change from James, right?) But after trying a few different techniques and positions, she found that even she couldn't handle it. Be careful what you wish for, we guess?

Are we the only ones who think Charlotte gave up on this guy too quickly? He was cute (check), he was fun (check)... and he was a freaking pastry chef! (Triple check! Bold and underlined!) But Charlotte worried that he was secretly gay — even though they had amazing sex — and dumped him for being too feminine. Your loss, Miss York.

Carrie definitely had good chemistry with this hyper-caffeinated, porkpie hat-loving jazz musician played by Craig Bierko. He hung around for two whole episodes... and gave her the biggest orgasm of her life, thank you very much. His scatterbrain ADD personality eventually got to be too much for her to stand, but we kind of liked his cool hipster vibe. Plus, he made Mr. Big uncomfortable, which we always appreciate.

Did this guy even have a name? Does it even matter? No, it does not. Charlotte's rose started to blossom when she fantasized about a romp in the soil with this gorgeous gardener who worked on her husband Trey's family estate — and we can hardly blame her. Even Bunny just laughed it off when Charlotte was caught smooching him... so hey, go get him, Charlotte!

Carrie's dalliance with this twentysomething dude was certainly invigorating: He had a tongue piercing, he knew all the right bartenders... and it helped that he was played by a young Timothy Olyphant. Sure, she later found out that he lived in filth with roommates, like every other guy in his twenties. But Carrie, you make inexplicably good money for a newspaper columnist! Be a sugar mama for a bit and keep him around for at least a second episode!

Hey, remember Skipper? This whiny sad sack with a thing for Miranda was nearly a full-time cast member in the first couple seasons, constantly begging Carrie for dating advice. OK, he was no Brad Pitt, but keep in mind, he was a "website creator." In 1998. In other words, Miranda rejected potentially the next Bill Gates who was head over heels in love with her. She could do a lot worse!

Carrie had a nice, easy rapport right away with this fellow patient of her therapist's, played by rocker Jon Bon Jovi. It's good to know he's open to working on himself — and who could forget that sexually charged game of Twister? He did later confess that he loses interest in women once he sleeps with them... but maybe therapy could help him with that! Carrie threw in the towel too early here, we're thinking.

Better known as "The New Yankee," this strapping fella was just called up to the big leagues when he started going around the bases with Carrie. He was handsome, he wasn't a total Neanderthal... and do you know how much money MLB players make? Carrie eventually blew him off because she was still hung up on Big. We're pretty sure this guy rebounded quickly, though. (Oops, sorry, wrong sport.)

This guy, aka "Mr. Fix-It," kind of came and went quickly in Charlotte's life: an out-of-work actor who made extra cash as a handyman. She was friends with him already, he was cute — and again, he fixed things around the house. What exactly was the problem here? They split up, and Tom moved back to Salt Lake City... but maybe Charlotte let the perfect man slip through her fingers.

This fashion photographer shared Carrie's passion for couture — and how many straight guys could you say that about, huh? He was romantic, he was artsy and he had access to all the best runway shows. But after a one-episode liaison, Paul mysteriously disappeared without a trace. (The show didn't even give him a weird sex kink to explain it.) Carrie, hang in there for the free issues of Vogue, at least.

This swaggering gent was touted as the male Samantha, and he even inspired her to go get her first AIDS test because she wanted a ride in his leather sex swing. She tested negative, they had a great time swinging... but by the next episode, Tom was gone. We get it, they both got what they wanted out of the deal, but Tom seemed like a worthy partner who could actually meet all of Samantha's many needs. Oh well.

Maybe we're just naturally charmed by John Slattery (#RogerSterling4eva), but we really liked Carrie with this quick-witted politician. He was smart and funny, they could smoke cigarettes together... and they got along so well, he stuck around for two episodes. Yes, he confessed to an offbeat sexual quirk (golden showers, anyone?), which Carrie promptly broadcast to the world in her column. But that's hardly disqualifying for public office these days.

This smooth-talking music executive was one of Sex and the City's rare boyfriends of color, and he and Samantha definitely found a nice rhythm together. In a particularly ham-fisted twist, though, his chef sister didn't like him dating a white woman ("it's a Black thing!"), and they had to amicably part ways. We wish we had seen more of Chivon... but we also don't trust the show to handle a relationship like that properly, so maybe it was for the best.

Carrie reconnected with her high school flame, played by the always appealing David Duchovny, and they quickly discovered that old spark was still there between them. The problem: He had emotional issues that he was sorting out with a stay at a mental institution — which this show tactfully depicted with raving lunatics running away screaming from orderlies. Yes, he wasn't ready to jump into a relationship, but at least he was actively working on himself! Which is a lot more than we can say about most of Carrie's romantic partners, including...

Alright, let's start with the positives: He's rich, he's dashing, he's an old-fashioned gentleman and he had a playful banter with Carrie that made their relationship more than just physical. But he also proved himself on numerous, numerous occasions to have the emotional intelligence of a ten-year-old boy, and he only wanted Carrie when he couldn't have her, up to and including their reunion in the series finale. (And for the purposes of this list, we're not counting what happens in the movies, but him ditching Carrie at the altar is an all-time unforgivable dick move.) Carrie and Big were toxic together, and her best friends all knew it, but the show insisted on selling them as this great love story anyway. We're not buying it.

We know there's a strong #TeamHarry contingent out there, and we liked him, too: He was totally devoted to Charlotte and didn't have the narcissistic hang-ups that bedeviled so many men on this show. But there was something missing here; it felt like the show was in a rush to pair Charlotte off by the end of the series, and had her settle for someone who is so not her type. (Plus, he was originally her divorce lawyer, which is all kinds of unethical.) We get that opposites attract, and Charlotte certainly deserved a man who worshipped the ground she walked on, but the palpable lack of chemistry between these two has us searching for another pairing for her...

As with Charlotte and Harry, Samantha's romance with this lovably dense actor was sold as her perfect match by series' end, and to his credit, Smith was surprisingly mature and loving, bravely holding her hand through a tough cancer battle. (And he certainly kept up with her in the bedroom, which is a non-negotiable for Samantha.) But he was a little too placid as a character: a blank slate that existed only to support Samantha, without challenging her intellectually. Smith was a nice fling, but not a life partner.

Yes, Sex and the City had a notoriously spotty record on incorporating characters of color, but late in the game, they finally got it right. TV staple Blair Underwood played this attractive doctor (for the Knicks, Stevie, the Knicks!) who caught Miranda's eye when he moved into her building. Robert was a dream boyfriend, effortlessly fitting into Miranda's harried single-mom life. He did nothing wrong, really, but Miranda dumped him anyway after deciding to give Steve another shot. Oh well... he probably deserved better.

We can hear you gasping already: "Trey over Harry? How dare you?" Granted, Harry was probably the more sensible life partner for Charlotte... but Trey was the yuppie WASP of her dreams. He was cut from the same repressed upper-crust cloth as she was, and they did share an authentic connection, although one that was ultimately thwarted by his sexual inadequacies. Still, Charlotte's years with Trey were Sex and the City at its best — Kyle MacLachlan was a delight — and we wish they had found a way to make it work... for Bunny's sake, at the very least.

Samantha ended up with Smith... but we still think she never should've said goodbye to this charmingly smug hotelier. Richard was far from perfect, but he was the perfect match for Samantha: filthy rich, and filthy in the bedroom. Plus, they shared a playful, hedonistic worldview that made them a formidable power couple together. Yes, he cheated, but he did try to make amends, and anyway, we can't believe that Samantha Jones would let a dusty old thing like monogamy keep her from what she truly wanted. Sorry, Smith, but Richard was truly her Mr. Wright.

Nice guys finish last... at least in Carrie Bradshaw's love life. And this indisputably nice guy got his heart ripped out not once, but twice by her. What was she thinking? Aidan had an easygoing appeal, he had a great dog... he made furniture, for crying out loud. (That alone will save you thousands.) When Carrie callously cheated on him with Big, he took her back... and then she still wouldn't marry him! Yeah, his jokes were a little corny, and if anything, he didn't stand up for himself enough. But in the end, she treated him like dirt, and he did not deserve that. We're glad he ended up with a wife and a baby of his own — far, far away from Carrie.

On a list filled with stunningly handsome, incredibly rich men, how does a goofy-looking pipsqueak of a bartender manage to take the top spot? Because he's the best guy any of the four ladies ever dated, that's why. On paper, Steve and Miranda made no sense together, but they shared a great spark (and great sex), and his fun-loving personality helped Miranda to loosen up a bit, which she sorely needed. He was a doting father to Brady, and he was always loyal and loving to Miranda. (Again, we're not counting what happens in the movies, but his infidelity in the first one came out of nowhere and felt tacked on just to give Miranda a storyline.) Even the "just a bartender" complaint went away when he took the initiative to open up his own bar. Looking back, Miranda was the only one of the four women to end up with the guy who was best suited to her. Congratulations, Miranda: You snagged yourself a good one.