We Ranked These 27 SATC Boyfriends From Least To Most Dateable

In the immortal words of Samantha Jones: "You can't swing a Fendi Purse without hitting five losers. Where did all the great guys go?"

If anyone knows how hard it is to be single and looking, it's the women of SATC. Their dating adventures captured six seasons and two movies worth of our attention, spanning more than a decade of our lives. We've watched them go out with athletes, nerds, creeps, mama's boys, millionaires, and more, and learned valuable love-life lessons along the way.

Looking through their personal catalogs of exes, there are some who really set the bar high for relationships in the late 1990s and early 2000s. A lot of these dudes looked good, acted right, and took these women on amazing dates, from horse-drawn carriage rides to picnics in Central Park. On the other hand, there are more than a dozen flops in these girls' ex files. Remember Doug? Shudder.

Let's take a page from Carrie's book (a.k.a. fictional weekly New Yorker column) and look at these relationships from an optimistic perspective. "Maybe our mistakes are what make our fate," she writes. "Without them, what would shape our lives?" Put simply, lots of these men were mistakes. They might not be worth dating, but they're still worth remembering.

We've listed the SATC guys from worst to worth it so you can see for yourself how average (and how awesome) these characters truly were. Read through our ranking and see if you agree with our picks from least to most dateable.

27 Aleksandr Petrovsky

via Vanity Fair

This guy is the one from Russia who makes Carrie move to Paris. He's guilty of enforcing his own values of 'men being the breadwinners of the family' onto her own plans and ambitions. Basically he wants her to be a stay-at-home wife. In Miranda's words, "I want to enjoy my success, not apologize for it," and that's just what Carrie ultimately decides to do.

She doesn't get away from this controlling dude fast enough to escape his fist, unfortunately. In one passionate argument in Episode 20 of the show's 6th season, he lays a hand on Carrie. That's the lowest of the low, making him the least dateable person on this list.

26 Richard Wright

via HBO.com

Do you remember when Samantha was running around NYC taping posters of a guy's face on every telephone pole she could find? The posters had words like 'LIAR' scribbled across them in black sharpie, if that rings any bells. This was part of the grand finale of her relationship with Richard.

Richard was the first guy Samantha ever felt truly deep feelings for. That's probably because he was more or less the male version of her - independent, powerful, and completely liberated. This all falls apart when he steps out on her. We love Samantha, but her male version? That's a no from us.

25 Wade A.K.A. ‘Power Lad’

via SATC Wikia

Wade is one of those guys who prove that age is just a number. Even though he's just as old as Carrie, he seems decades younger as far as his interests and maturity level are concerned. Carrie, what were you thinking?

She meets him at a comic book store, which might actually make a good meet-cute IRL. She then ignores the red flags that he GOES BY THE NAME 'POWER LAD' and still lives in his childhood bedroom. Big mistake. He blames her when his mom finds illegal substances in the house, and she takes that as her cue to exit the relationship. We're way ahead of you, girl.

24 Harvey Terkell

via Uproxx

Samantha dates successful businessman Harvey Terkell in Season Two. He seems great, especially since he's independently successful enough to hire a housekeeper. His relationship with the housekeeper actually ends up being the cause of their eventual breakup.

The housekeeper is rude to Samantha, and this dude takes his housekeeper's side every single time - even when the housekeeper becomes physical with Samantha! Anyone who is okay with this kind of behavior is not okay with us. He's a bit more dateable than Aleksandr, Richard and 'Power Lad,' but does that make him a catch? Absolutely not.

23 Doug

via Uproxx

We all love a good nap in the daytime every once in a while. We love eating junk food late at night. Who doesn't? Taking it easy is a perfectly good way to spend some days, but not every day. Lazy and unhealthy habits kind of made up this whole character's identity.

He briefly dates Miranda in Season Four. Why briefly? Soon into the relationship, he decides to use the bathroom while she's in it brushing her teeth - and he doesn't use it to brush his teeth. Stinking up someone else's space when they're standing right there is not a good way to start a long-term relationship. Pass.

22 Seth Robinson

via Closer Weekly

Jon Bon Jovi, is that you? Yes, but in the magical pretend Manhattan of the SATC universe it's also a guy named Seth Robinson. Carrie meets Seth in the waiting room of her therapist's office when she decides to see a therapist for the very first time.

Seth and Carrie have a great night together and everything about him seems to be cool. Eventually Carrie couldn't help but ask (sorry, "Could't help but wonder") exactly why he chose to go to therapy, and he discloses that he has a problem with relationships. As you might already predict, she never sees him again. Sorry, but ghosters aren't dateable.

21 Bill Kelley

via PressForm

Bill is part of Carrie's brave attempt to date older men. As she puts it, "Men in their forties are like the New York Times Sunday crossword puzzle: tricky, complicated, and you're never really sure you got the right answer."

He's also a politician who dumps Carrie because he thinks her job is too out-the-box to be connected with him and his campaign. This comes across as both selfish and insulting to Carrie's career as a serious columnist. And everything else was going so well between them! A guy who puts his career above ours? We've got to pass on that.

20 Barkley

via TV Guide

Barkley (played by Gabriel Macht of Suits) is a friend of Carrie's who we meet in Season One. He's an artist, which is cool, but he also happens to be obsessed with getting with models. Carrie has a special word for men like this. She calls them modelizers.

"Modelizers are obsessed not with women but with models, who in most cities are safely confined to billboards and magazines, but in Manhattan actually run wild on the streets, turning the city into a virtual model country safari where men can pet the creatures in their natural habitat."

Yikes. We prefer equal-opportunity daters.

19 Trey MacDougal

via Vogue

Trey MacDougal is Charlotte's first husband, to whom she accidentally proposes over a romantic dinner. His response is all Carrie needs to hear to know this guy isn't the one. "He said all righty?" Carrie asks Charlotte when she breaks the news. "Now I’m thinking the upsetting thing isn’t that you proposed, it’s that you proposed to a guy that says 'all righty.'"

This relationship goes from bad to worse when Trey - who is otherwise absolutely perfect on paper - can't set boundaries for his overbearing mother, Bunny. His mom is always sticking her nose in his relationship, and he is always taking her side. Bring on Harry the divorce lawyer, please!

18 Mr. Big

via Scoop Whoop

Ugh. Remind us how this guy is supposed to be Carrie's soulmate again? He [spoiler alert] leaves her at the aisle! She put a bird in her hair and he couldn't even get out of the car! Clearly we’re still not over it.

Big's red flags were waving way back in the beginning of the series. He treats Carrie like something disposable but gives her just enough charisma to keep her coming back every time. "Did I ever really love Big," she asks in Season Two, "or was I addicted to the pain?" We don't know, but we do know that besides for his bank balance, nothing about this dude is dating material.

17 Jack Berger

via Entertainment Weekly

Berger should be Carrie's perfect match. He's a cute young writer with a great sense of humor and a similar outlook on life as she has, besides for disagreeing about whether or not scrunchies are formal wear. By the way, we are firmly on Carrie's side in this argument (they're not). Unfortunately he's responsible for possibly the worst breakup of the entire series.

After dating Carrie solidly for what seems like months, Berger has the bad etiquette to leave a post-it note ending their relationship for her to find. That's right, this is the guy who dumps her over a POST-IT. It's like the text breakup before texting was a thing. Unforgivable!

16 Keith Travers

via Hollywood.com

Yep, this guy is Vince Vaughn. At least, he's a character played by Vince Vaughn, but let's be real: the character of Keith is a fun-loving guy who lives in Los Angeles, California, and attracts Carrie with his wicked sense of humor. That sounds like Vince Vaughn to us.

His flaw? To impress Carrie, he pretends that houses he's showing (he's a realtor) are his own. They actually belong to the Hollywood elite, so he's big-time lying to her face. Telling lies (even with the intention of just impressing someone) drags him down to this position on our list. Dateable? Maybe, but not a perfect catch.

15 ‘The New Yankee’

via Elle UK

Carrie dates the so-called New Yankee after the first of many splits with Mr.Big in an attempt to make Big jealous. It's a super high-profile relationship because this guy has just been signed to play for the New York Yankees, making him the perfect way to show the world (and Big, if he reads the gossip pages in the paper) that she has moved on.

The perfect rebound, this dude looks great on Carrie's arm and has an impressive athletic career going on. So why was he just a rebound and not something long-term in Carrie's life? His main shortcoming is in the personality department. A bland boyfriend isn't really what we're looking for.

14 Kurt Harrington

via The Cut

Kurt Harrington was Carrie's high school boyfriend, and there wasn't really anything wrong with him. He was attractive for someone in the '90s, although these days that gel-spiked hair is a no-no. He was fun and friendly, and he and Carrie had great chemistry. The downside? It's not usually a good idea to date an ex. It didn't work then, so why will it work now?

Kurt comes along with a whole lot of memories and emotional baggage for Carrie. In her own words, "Maybe the past is like an anchor holding us back. Maybe you have to let go of who you were to become who you will be."

13 Vaughn Wysel

via Yahoo

Like Berger, Vaughn shares Carrie's kind of career. He's a fiction writer and he's pretty good at it. By the time Carrie dates him, he's a household name in the publishing world. Everything goes smoothly with Vaughn (Carrie even gets along with his family) until she has a few complaints about his relationship skills.

Vaughn takes this criticism way too personally and the relationship falls apart from there. We'd like to think that with a little patience and compassion this guy could change his ways and bring his romantic skills up to the level of his writing skills. He seems like a good catch otherwise.

12 Justin Anderson III

via Elle

Justin Anderson III is Charlotte's idea of a perfect man. He comes from a wealthy family, believes in the same kind of conservative traditions that she does, and finds her to be both pretty and smart. ("I'm pretty AND smart" she tells the girls in Season Three. "I'm a catch!")

This guy is basically blameless when he ends things with Charlotte after she lies to him about being divorced (she was only separated from Trey at the time). Her telling this lie was a deal-breaker for him, and we can't blame him for that. We can even appreciate his commitment to honest living. The dude is dateable.

11 Dr. Robert Leeds

via Pinterest

If anyone deserves to date a dreamy doctor, it's Miranda. This doctor isn't only gorgeous and hard-working, he's also really loving and kind towards everyone we see him interact with on the show.

Miranda breaks it off with Robert when he gives her a cookie that says 'I love you' on it at a point in their relationship that she considered to be too early. We agree that it can be hugely uncomfortable when someone shares this with us before we're ready, but come on! A cookie is harmless and cute, especially when it comes from a guy who looks this good.

10 Sam

via IMDB

Before winning over fans on shows like Justified and Santa Clarita Diet, Timothy Olyphant played Sam on SATC. Sam was a character in his early 20-somethings who dated Carrie while she was in her early 30-somethings. She credited him for reminding her how nice it was to kiss someone for hours and hours.

The issue? Sam's age turned out to be a problem when Carrie wakes up in his ultra-immature bachelor pad, complete with lava lamp and empty pizza boxes collecting grime on his counters. However, we can't really fault a guy for his age. Give him a few more years and this hottie is definitely worth dating.

9 Roger Cobb

via Vanity Fair

Roger has his time in the spotlight as Miranda's new guy near the end of Season Two. He's good looking, smart, and totally into her for being the strong, independent woman she is. Things don't work out because he has a young son from a previous relationship who walks in on Miranda while she's in a compromising position that may or may not involve clothes.

The end of this relationship seemed more like the kid's fault than Roger's himself! We can't fault a single dad for trying to date while also trying to raise a kid. The simple solution of a lock on his bedroom door would make this guy a great catch.

8 Ray King

via 2Paragraphs

Remember Ray? We forgive you if you don't. This dude had a brief appearance on the show as Carrie's rebound after breaking it off with Mr. Big in Season 4. We think he deserved more than what he got, which was a two-episode arc and getting dumped.

Carrie didn't see things going far with Ray because he was a musician who was so passionate about his craft that he would break out his guitar at random times and serenade her. They otherwise had great chemistry, but he just vibed on a more creative frequency than she did. We hope you found your muse, rebound Ray!

7 Sean

via EW

Carrie dates this super-cute younger guy in Season Three of the series, and ends up breaking up with him for reasons that today's critics find "problematic," according to Indy100. Up to this point Carrie had only dated men who were straight (which to be fair is the case with most of us) but surprisingly to her, Sean is a character who played for both teams.

It's not like he was trying to date multiple people at once, he just had a variety of people in his own dating history! We don't consider this to be as bad in 2019 as Carrie did in 2000, so cutie Sean makes it high on this list.

6 Stephan

via PicsOfCelebrities.com

This guy is at the center of another SATC storyline that definitely wouldn't fly with audiences in 2019. He was the cute pastry chef from Chelsea who Charlotte dated briefly in Season Two of the show, and there was pretty much nothing wrong with him.

He had a fun personality, impeccable grooming habits, and Charlotte's big three: "looks, manners, money." She dumped him because these qualities actually made him seem too feminine for her, especially after he yelled when he saw a mouse. Femininity isn't a bad thing, masculinity is diverse, and mice can be scary! We think you're still worth it, Stephan.

5 Skipper Johnston

via The Sun

Every male character on SATC comes with their own unique problem. Skipper's problem? He was "too nice" for Miranda's taste. She thought his kind, polite, and generally sweet behavior was a turn-off, but as far as dating potential goes, these qualities actually put Skipper close to the top of our list.

We understand that sometimes everything can be right except for the chemistry. That was basically Miranda's case with this sweetheart. He was too predictably nice to make any sparks fly. We're glad he ended up being a reoccurring character though, because this dude deserves love! We bet there are more women out there who'd say yes to Skipper than there are who would, well, skip him.

4 Smith Jerrod

via Yahoo

As far as boyfriends on this show go, Smith Jerrod was almost perfect. He had a great modeling career, an open mind for Samantha's crazy escapades, and a heart that beat only for her from Season Six, Episode Two and beyond. He even sticks with her through chemo.

Smith was a loyal, supportive, and adventurous BF right to the end, when [SPOILER ALERT] Samantha broke it off to pursue a deeper relationship with - well, herself. The only reason he isn't number one on this list is because for all his strengths, we find him to be kind of bland, like a one-dimensional stereotype of a male model. But dateable? Absolutely.

3 Harry Goldenblatt

via Buzzfeed

When Charlotte was getting a divorce and dealing with one of the worst times of her life, Harry appeared like a knight in shining armor and saved her from ever having to withstand another bad relationship. He's like her love life guardian angel, and we are here for it.

From his first appearance on Season Five to storylines in both of the SATC movies, viewers never see Harry disappoint her. All he does is worship Charlotte, take care of their beautiful children (while not even getting distracted by a hot Irish nanny) and honor the commitment he makes to her from day one. He's a keeper!

2 Steve Brady

via HBO

You might be surprised to see Steve above Harry here, but guess what? This character grew so much over the course of the series (and movies) that we feel he deserves a prime spot on the dateable end of this list.

From his accent to his style to his sense of humor, Steve Brady is one-of-a-kind boyfriend. He goes from bartender to bar owner in a matter of seasons. He convinces Miranda (Miranda!) that men can be worth dating long-term. Plus his genes made a cute baby, if you're looking for that in a potential fictional partner. For the complex relationship he was able to sustain with Miranda since the show's second season, we place him at number two.

1 Aidan Shaw

via Cosmopolitan

Here he is: our number one! Earthy, flirty, laid-back Aidan is everything that Mr. Big isn't, and that's a good thing. He has a creative career in carpentry. He has eyes only for Carrie while they're dating. He encourages her to be her best self by supporting her ambition to quit smoking. Plus, he has an adorable dog.

If you're unfamiliar with how Aidan's storyline ends, we won't spoil it for you. Let's just say that this babe did not get the same amount of love, loyalty, and respect that he put into his relationship with Carrie in return. Forget the haters who say this pair wasn't meant to be! #TeamAidan4ever

Sources: Indie Wire, Vanity Fair, Elle, TV Guide, Indy100

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