2 Adult Sex and the City Virgins Discuss Their First Time


For the 20th anniversary of Sex and the City—which premiered on HBO on June 6, 1998 and went on to become iconic prestige television—Jezebel is doing a week of posts dedicated to our favorite band of sexual women friends.

Our names are Kelly Stout and Ashley Reese and we had never watched Sex and the City until last week. Can you believe it? We finally did*, and then had a series of discussions about it. Turns out “Sex” and “the City” is about more than just sex or the city. Our conversation follows.

*(For the most part. We skipped some.)

Kelly: Ashley, I feel we must begin with the obvious question. Do you feel you are a Carrie, a Miranda, a Samantha, or a Charlotte?

Ashley: So I feel like I have Charlotte’s neuroticism and Carrie’s tendency to be super emotionally driven and overshare about her sex life. I had a sex column for a little while, too, and while the perspective was incredibly different, I feel a bit of a kindred spirit with her self-centered ass on that front.

Kelly: I don’t think you’re self-centered, but we can set that aside momentarily so I can talk about ME. I am a Miranda with Carrie tendencies. Did you watch the ep where Aidan [Ed. Note: In the original draft of this story, Ashley and Kelly kept spelling Aidan as “Aiden” and referred to Trey as “Tray,” which proves how much they know about SATC.] runs Carrie a bath?

I have complicated feelings about Steve based on the episodes I watched.

Ashley: Yes!

Kelly: I’m so glad because I want to discuss it so badly. I found it very creepy that Aidan ran her a bath and was like, “Let’s not have sex…This is just for you.” But I can’t quite articulate why.

Ashley: Something about Aidan just rubbed me the wrong way. It was like the most unappealing type of bullshit chivalry. I mean, I would have been more annoyed if he didn’t decide to join her in the bath in the end but still…like…bro, what? Also that bathwater looked dirty. Speaking of dudes, the men on this show…the love interests…WHEW!

Kelly: Who was your favorite?

Ashley: God…none of them??? I have complicated feelings about Steve based on the episodes I watched. I found him endearing in a puppy dog needy way.

Kelly: Did you watch the one where he has skid marks?

Ashley: No, but now I have to.

Kelly: Here’s the basic idea: Miranda is doing Steve’s laundry, and he has apparently semi-pooped his pants.

Ashley: Thats really laying it on thick with the whole “Miranda is an adult, Steve is a man child” thing.

Kelly: I’ve noticed they love to lay shit on thick. It’s like…I get it. This is the episode where the theme is maturity, or religion, or…how Charlotte is afraid of everything. Like a procedural, but the procedure is sex. Remember jazz guy? Ray…?

Ashley: GOD…

Kelly: Imagine having only one interest.

Did you watch the one where he has skid marks?

Ashley: As someone with ADD…I was almost offended by his portrayal. But just almost. We already know this is a super politically incorrect show by 2018 standards and honestly I’m fine with watching media like that. But like, I don’t know, he didn’t seem like he had ADHD. He seemed like he was just on speed all the time! I don’t mind an ADHD joke, but I was like “…lol okay, SATC.”

Kelly: Oh yeah, that episode also had a fun take on binge eating. Not to mention, Samantha’s relationship with Maria and her discovery that “we have three holes down there.” This episode really had an a la carte menu of things sex and the city does badly.

Ashley: Did Samantha only discover her urethra when she dated a woman?

Kelly: I’m trying to remember if there was shitty race stuff in that episode.

Ashley: I don’t remember too much shitty race stuff in that ep. Though that’s easy for the show to avoid when very few people on it are non-white lol.

Kelly: Indeed. Man, lots to talk about in this episode. It’s really a minefield because it has a lot of Trey in it. My enemy.

Ashley: I…don’t know how I feel about Trey. AKA Twin Peaks Dude. AKA Mayor From Portlandia Dude.

Kelly: AKA The Body That “Schooner” Is Attached To.

Ashley: Jesus. Schooner. My real enemy.

Did Samantha only discover her urethra when she dated a woman?

Kelly: Let’s talk more about Charlotte. When I was in high school, I remember a few girls from my class had watched their moms’ copies of SATC and were sitting around discussing how they were all Charlottes, and they were saying that she’s the “classy” one. I was then sort of impressed, but now, as a grown up human, I see that Charlotte is a very, very young-seeming adult. Her fear of sex, and thinking that you can’t live with someone until you’re married seem like the kinds of ideas only a Republican teenager would have.

Ashley: Her and Trey not having sex throughout their engagement was wild to me. It was very promise ring adjacent, but she was a grown woman who had already fucked so…uh?

Kelly: She is very devoted to what she sees as what marriage and family life looks like, but all of these things are making her miserable.

Ashley: I watched an episode in which she breaks it off with a guy because his taste in china is different than hers. Otherwise, they seemed very compatible.

Kelly: She’s a psycho and I love it.

Ashley: I kind of love her too. But god, she sounds so immature!

Kelly: I definitely hate her, but she’s fun to watch because she makes me feel normal.

Ashley: She definitely validates a lot of my weird neuroticism.

Kelly: She’s the most maladjusted character in all of TV?

Ashley: Watching her is stressful. I wonder if she would be happier in the regency period or something.

Kelly: I just realized something.

Ashley: Oh? What?

Kelly: I had conflated Skipper and Steve into a single composite character in my head.

Ashley: They looked kinda similar.

Kelly: Boyish. Worked at…bars?

Kelly: I feel like we’re going to have to talk about the abortion episode.

Ashley: Okay, at first I was kind of amped that this was going to be an episode in which a woman got an abortion, because so many TV shows and movies do that thing where the woman changes her mind at the last second, so I was like, “Wow, SATC did that!”

And then, well…Miranda didn’t get the fucking abortion.

I did like the subplot of Carrie thinking about the abortion she had, and not feeling guilty, though. I also had fun doing the math and realizing that Carrie’s aborted kid would be around my age now. Like, maybe a year and some change older.

Kelly: I liked that a character got a chance to explain why she needed/wanted an abortion and got to articulate how happy she was that she had done it. The ep was a wild ride for me emotionally because in the end, Charlotte exclaims, “We’re having a baby!” when she finds out Miranda is keeping it. I was moved by her choice of pronouns.

Ashley: Yes, that was cute. And I really did feel bad for Charlotte having trouble getting pregnant. As petty as her anger at Miranda and her fertility was, I understood it.

Kelly: She and Miranda are such good friends to each other in this arc though. When Miranda follws her home, I found it really moving.

Ashley: I loved the idea that Charlotte felt safe with Miranda behind her, even if she was salty.

And then, well…Miranda didn’t get the fucking abortion.

Kelly: Every now and then, this show articulates friendship in a way that feels very down to earth to me. For all of their craziness about men, and underdeveloped thinking about them, these women seem to do a lot of looking out for each other, giving each other space, and meeting each other where they are. They never really have drama that lasts more than a minute.

Ashley: And like, as much as we can clown the cloying bougieness of their little chitchats over brunch, they’re sort of sweet.

Kelly: I don’t think I would have understood that as a young person watching this show. It took me growing up and having adult friendships to see that their friendships give them a lot of room to be themselves.

Ashley: I think the older I get, the more I yearn for and appreciate moments to just sit somewhere, at a restaurant, with some friends, and catch up. They all are who they are.

Kelly: Which is…batshit nuts about men.

Ashley: Frankly, I don’t need this show to pass the Bechdel test.

Kelly: Did you watch the episode in Atlantic City?

Ashley: Okay, that fucking episode. I liked Steve enough, but he infuriated me in that one.

Kelly: No offense, Katie, but it was the least hot thing imaginable. “I can’t do this.”

Ashley: He was too scared to watch his baby for ONE FUCKING WEEKEND. I was livid.

Kelly: Oh brother. What a complete loser.

Ashley: 2) I felt really bad for Carrie.

Kelly: What happened to her again?

Ashley: She just really wanted to hang out as a gang, and everyone was kind of in their own heads. They all came together at the end, in such a sweet way, but god. It was like pulling teeth to get there.

Kelly: I couldn’t decide if she was trying too hard to make the old days happen or if she was just trying to get the gang to have a nice time.

Ashley: Oh, she was definitely trying too hard, but I still felt for her. She was goin’ through it lol. 3) Samantha’s iconique line: “I love you too Richard, but I love me more.” I’ve heard of this line for ages and it was nice to finally hear it/see the scene.

Kelly: Same. I knew about that line from Maddie, and I’d sort of imagined it coming at the end of a very different plot arc. I really liked that it didn’t really come after shitty behavior from him, exactly, but more out of her tormenting herself about potential shitty behavior. Like she was just takin’ care of herself! It wasn’t like, revenge.

I couldn’t decide if she was trying too hard to make the old days happen or if she was just trying to get the gang to have a nice time.

Ashley: This was true self care. Extremely superficial side note but, Charlotte looked AMAZING when she changed out of her dowdy clothes and wore that dress with the plunge neckline. I was shook.

Kelly: I completely agree. It was A LOOK.

Ashley: I’m like, “DAMN GIRL WHERE YOU BEEN?” She had the juice.

Kelly: Ok wait a tick. Look at this tweet:

Kelly: This makes me think we missed an important plot point about Richard.


Kelly: !!!!!!

Ashley: That episode had so many damn layers. But before we get into the sex stuff, I need to make an observation. What really got me about that episode was that it was such a sign of the times regarding the crew’s complete apathy to politics. Clearly pre-Bush. Not that the average person today is super politically engaged, but Samantha’s line that went something like, “I don’t care about the Democratic Party or the Republican Party. I just like parties!” Like, laughing about not being registered to vote? Bye.

I get that it’s supposed to be funny, I’m not devoid of a sense of humor, but can you imagine a show today about a group of educated white women in their 30s in NYC who are that politically apathetic?

Kelly: Girls.

Ashley: ….

Kelly: (Sorry, just kidding don’t wanna open that can of worms again.)

Ashley: I mean, fair, in a way! But I think that SATC was “aspirational” in a way that Girls wasn’t.

Kelly: Totally. But back to this ep. The fact that she outs him as a person who enjoys consensual pee play for basically no reason gave me pause. Especially because I agree with Katie [McDonough, who once expressed on Slack] that they could have figured out a workaround for that.


Ashley: That was kind of sus. But I also thought he was a dick for being like, “Oh yeah my advisors don’t think we should see each other anymore,” after she said she wouldn’t pee on him! Even though she was like, “Naw bro, can I just like pour warm tea on you?”

Kelly: I thought she made a good faith effort to compromise!

Ashley: He wanted that PEE. That legit URINE. Fuck tea.


Kelly: It’s funny that she would be dating a politician when she isn’t into politics. What did they talk about? Pee, I guess.

Ashley: Yeah, she was in it for the glamour. Being Jackie O of the ’90s.

Kelly: And all she got was pee.

Ashley: Classic NYC love story.

Ashley: We haven’t really talked about the ending.

Kelly: I watched “Splat!”

Ashley: What did you think? I loved the party girl.

Kelly: I was moved almost to tears.

Ashley: And I hate Carrie’s man!!!

Kelly: Yes, he is so boring and terrible. Smith is the only good man. Besides Stanford. Sanford?

Ashley: Which one is Smith again?

Kelly: Samantha’s hot boyfriend who is also nice.

Ashley: Yes he is GOOD.

Kelly: Yes, I love the Samantha chemo storyline, and I loved the way Smith went to therapy because it was stressing him out. So self-actualized and normal.

Ashley: I was incredibly frustrated that she went off to Paris with that guy and was willing to drop everything that was important to her for an IDEA of a glamorous life in Paris. But I really loved the way they emphasized how much she stupidly sacrificed for his affection when she abandoned a dinner with some fans of her book to go with Alexander (or whatever his name was) to his soft opening at the gallery. When she finally left (AFTER FINDING HER CARRIE NECKLACE AND REMEMBERING WHO THE FUCK SHE WAS) and got there only to see that everyone was gone and that they used her book as a coaster…WHEW. The romance with Big coming to Paris was…kinda cute I guess but THAT PART got me.

All and all, did this show age well? Eh, not really.

Kelly: I completely understood why she did it. She was stuck in a rut and Paris seemed smart, and “Splat” had just happened and it seemed like the party was ending. She was bored of being the party for her friends. HOWEVER, I completely relate to your frustration. She sacrificed herself under the guise of doing something for herself, which is one of my big fears. But again, her friends are the best! They’re like, “Babe don’t do this.” They’re not sitting there being like, “Well, when you have trouble making a decision, it’s probably because there are two good options.”

Ashley: But she NEVER felt good about it?

Kelly: She was so defensive about it.

Ashley: She was mostly beating herself up because she figured she was supposed to be enjoying herself and god it got tough to watch. Her gut KNEW.

Kelly: There’s a great line spoken by Charlotte when she’s with her friend shopping for something: “Can you believe this is finally happening? I hope nothing goes wrong.” She’s talking about her baby, but it’s like, really she’s talking about Carrie. You’re finally moving on, Carrie, I hope nothing goes wrong! But it heckin’ does!

Ashley: Sure does! Also the slap…That felt a little tacked on??? And Big being mad for two seconds before they fall into a fit of laughter…LOL K?

Kelly: I’ve never believed them as a couple. Everything they do feels put on. Sorry if you don’t agree. (Feel free to be wrong in the comments!!!)

Ashley: Ugh, but I’m mad that this show had me rooting for Big. I was like, god, anything to get her away from this artiste who doesn’t know about “Piano Man.”

I’m glad I didn’t watch it earlier, personally.

Kelly: He’s no fun and they’re clearly not meant for each other, and I have such a soft spot for people who want to be together finally getting together (who doesn’t). I just wish he weren’t so…himself.

Ashley: I did like the other B plots of the final episodes too, though. Samantha’s chemo battle and her sex-drive woes, Charlotte and the adoption drama; Miranda and struggling with Steve’s mom who clearly had dementia.

I was a sucker for Carrie and Big getting together and Carrie returning to NYC, but the last eps emphasized the other characters’ growth a lot. Can you imagine Season 1 Charlotte reacting to the bad adoption news at that breakfast with the prospective adopters from North Carolina in the measured way she did in that ep?

Kelly: NEVER.

Ashley: All and all, did this show age well? Eh, not really. Did I have my frustrations with it? Sure. But I’m also a little disappointed that I didn’t watch this show earlier. It’s genuinely pretty damn entertaining. I think when a show has so much mythology behind it, it can be a little daunting to just jump in. I clowned people who decided to move to NYC because of Sex and the City, but now I’m a little more empathetic. I can see how this show had a powerful influence on young Gen-Xers and older millennials.

Kelly: I’m glad I didn’t watch it earlier, personally. I think I would have had a far less openhearted response to it. Now it feels like good, clean fun, but I think I would have felt in some way challenged by it when I was younger and trying to figure out What Kind Of Woman I Wanted to Be.

Ashley: That’s fair, too. I’m glad I went into this with pretty empty expectations despite its notoriety. It made following the adventures of these four maniacs a lot more fun.

Kelly: I would have felt sort of trapped by the cheesy dialogue, the rhythms of the relationships they have, and the contours of their professional lives. Like I would have spent all my time shouting at the screen: “People aren’t really like this!” It’s really helpful to be older and to see that this is sort of just for fun. It sounds stupid to say that, but I think it’s sort of the same reason you don’t want to feed kids candy. They’ll get too hyper and they don’t grow. If I’d seen this when I was younger, it would have made me hyper and I wouldn’t have grown. In other words, I can’t help but wonder if this is better as a dessert.



Ashley: Word.

Kelly: It’s like…did the show age well? Hard to know. Did I age well?

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