It’s Time To Revisit These 9 Fleeting Sex & The City Hookups

Seinfeld may be the gold standard of having the one-episode love interest who gets cast off with a wacky dealbreaker — how could Jerry possibly be expected to commit to a woman who ate her peas one at a time? Or a girl who shushed him while watching TV? (“Hey! I got a real thing with shushing!”) But Sex and the City came in as a close second, with four female characters who would each be saddled with a guy to dispose of in every episode.

And so what a delight to see the form resurrected in the latest episode of And Just Like That, in which Carrie Bradshaw has a bike-lane collision (“Gangway for foot-cycle!”) with a tech dude played by Peter Hermann. First, can I just say that Peter Hermann is exactly the right level of famous to be a one-off SATC-verse guest star? Famous face but not a household name, handsome but not distracting. (For the record, the right level of fame for a guest star is a New York City working actor who could plausibly appear either on Law & Order or in an acclaimed off-Broadway production of The Seagull.)

Anyway, Carrie accompanies Peter Hermann (his name doesn’t matter — he’s Peter Hermann) to an urgent care (where she once saw an Olsen twin!) and discovers that although he can’t afford to put his treatment on a credit card, it’s only because he’s invested all his liquid assets into a new app he’s developing with his platonic business partner. And though he said he was single on his urgent care intake form, Carrie realizes that he actually was married — at least, in all the ways that matter — to his business partner. “I hope you two have a long and happy marriage!” she shouts as she absconds from his loft.

To be fair, it seems like Carrie is overreacting a little bit. I didn’t really like the guy’s vibe, but still, his app presentation was the very next day. This might be a situation where you, I don’t know, give him a week or so to focus on the incredibly important work project and then ask him out to coffee to see how it goes. But Carrie is done with compromises, and I can’t blame her. She’s a rich woman in her 50s with multiple books and a closet full of absurd feather hats: There’s no reason she should tolerate a man who doesn’t wow her.

Still, in the hierarchy of dealbreakers, caring about your job seems relatively low-stakes. (I mean, come on, this is a woman who got broken up with on a Post-it Note!) And so, in honor of Peter Hermann’s untimely dismissal from the SATC-verse, I thought it fitting to revisit nine of my favorite guest star love interests from the original series and whether or not I find them undateable.

The Yale Guy With The Touchy Dad

Season 2, Episode 7

In the spirit of reclaiming her sexuality, Charlotte goes to a wedding wearing a low-cut black dress where she meets and becomes instantly smitten with a guy who went to Yale. Their relationship progresses to the point that she’s meeting his parents — but when his dad cops a feel, Charlotte tries to tell the boy, and he immediately shuts her down. Look: We’re not responsible for the behavior of our folks if they happen to suck. But we are responsible for how the important people in our lives are treated, and if someone tells you that they were being groped, replying that they were wearing a “slutty dress” is just defensive-enabling creep behavior. You’d think they would have taught him better at *sigh* Yale.

4/5 red flags: Bad enough to have a creepy dad, worse to be the type of guy who doesn’t #trustwomen.

Superhero Boy

Season 3, Episode 15

Carrie meets Wade (aka Power Lad) at a comic book store, and at first, he seems free-spirited and youthful until she realizes he’s just an overgrown kid who still lives with his parents. New York City rent is, uh, unconscionable, and so I don’t really have a problem with someone living with their parents (especially if that person is an artist, like a comic book creator! Save that rent money for self-publishing!). Where Wade falters is the fact that when his mom catches them smoking weed, he immediately blames it on Carrie. Narc behavior is extremely lame. At least Carrie gets to keep the weed, because there’s no way she’s interested in keeping the boy.

3/5 red flags: There’s always time for someone to grow up, but you don’t have to wait around for it.

Vaughn Wysel

Season 2, Episode 15

Justin Theroux appears in two episodes of SATC as a novelist named Vaughn, mere episodes after Theroux appeared briefly as an entirely different character. Still, Vaughn is great: He’s smart and funny, and best of all, he has a brash, fun Upper West Side intellectual family, including a mom played by the late Valerie Harper, that I want to adopt me. His dealbreaker is a bad case of premature ejaculation, which wouldn’t be a problem, really, if he was willing to talk about it. Instead, he’s defensive and shuts Carrie down. Hmm.

2/5 red flags: Worth dealing with for access to his family, but only if he promises to go to therapy.

Weight Watchers Guy

Season 5, Episode 4

Miranda dates a sweet and funny dude she met at a Weight Watchers meeting, whose only problem is that he eats her out too enthusiastically.

0/5 red flags: Let’s monitor our internal fat-shaming, Miranda.

Only Wants To Have Sex In Public Guy

Season 2, Episode 12

Miranda meets a guy named Jack (played by Will Arnett) because they’re both interested in biographies of historical figures. Cute! Less cute is the fact that he only wants to have sex in public. I mean, I get it: It’s hot. And as someone with a weird sexual attraction to Will Arnett’s widow’s peak (I don’t understand it either), it doesn’t seem like that bad of an arrangement to have illicit little trysts in alleys and taxi cabs and talk about Ron Chernow afterward. The problem here is that Jack is completely unable to have sex if there isn’t a risk of being caught. That seems like an issue for therapy, and it’s also a little unethical to be engaging non-consensual strangers (i.e., taxi drivers) in your little kink.

3/5 red flags: We all have our things, but this one is a little logistically challenging.

Open Door Guy

Season 4, Episode 3

Comedian Jim Gaffigan plays another of Miranda’s paramours who becomes so comfortable in their new relationship that he pees with the door open. That’s all well and good until he escalates it to number two. There’s a spectrum when it comes to romantic comfort (Carrie is probably on the far other side — remember when she was mortified because she accidentally farted in front of Big?). But romance requires a little mystery! Being relaxed with someone is all well and good, but the basic standards of privacy that we all learned as toddlers still apply.

5/5 red flags: Not because it’s inherently a personality problem, but because it’s just so gross I would never be able to look this man in the face ever again.

Pastry Chef Guy

Season 2, Episode 11

Charlotte finds the perfect man — a pastry chef (!) who lives in Chelsea, bakes for her every morning, and is apparently great in bed. Her problem is that she thinks he seems gay, and when he’s scared of a mouse in his apartment, it proves a bridge too far for Charlotte. That reasoning would never fly in 2023 or in the newly woke AJLT universe. We’re more evolved! Charlotte, who fully accepted her nonbinary child Rock, surely understands that sexuality can present a variety of ways! But alas, her close-mindedness has deprived her of fresh-baked muffins in the morning and a really good-looking dude.

1/5 red flags: I understand getting the ick from a dude who shrieks at a mouse, but that’s not worth giving up fluffy, homemade croissants.

Bisexual Guy

Season 3, Episode 4

Carrie breaks up with a guy mostly because he’s bi, and it weirds her out. She claims she doesn’t think bisexuality even exists and that it’s just a “layover on the way to gay town.” This bisexual dude is fun, cool, and deserves better than Carrie (although he waves a yellow flag for being an adult who still plays Spin the Bottle — leave that game at high school cast parties for Into the Woods, Jr., where it belongs).

0/5 red flags: Breaking up with a guy just because he’s bisexual is actually a huge red flag for Carrie, who is apparently the most closed-minded sex columnist in America.

Jazz Guy

Season 4, Episode 3

Carrie dates a fedora-wearing jazz dude who plays her like an upright bass, apparently in a way that she finds incredibly erotic. Still, when it turns out his attention span has a jazz-like tendency to jump all over the place, Carrie finds him hard to deal with. TBH, Jazz Guy should have broken up with Carrie first when it becomes obvious that she’s sort of using him as an accessory to make Big jealous, but if she’s able to tolerate the fact that he wears a fedora, he should be able to tolerate the fact that she clearly isn’t over her ex.

1/5 red flags: I don’t really have a problem with his manic energy, especially because he channels it into cool and artistic hobbies, but 5/5 red flags for the upright bass thing. (Maybe he would have been a better fit for Samantha?)