Sex and the City

Season 1 Episode 4

Valley of the Twenty-Something Guys

Aired Sunday 9:00 PM Jun 28, 1998 on HBO
out of 10
User Rating
143 votes

By Users

Episode Summary

Carrie and Samantha start dating guys in their twenties. Carrie dates Sam and at first all they do is kiss but it soon escalates to sex and Carrie breaks it off when she wakes up and sees his messy apartment and realizes that she's too old to date a guy in his twenties.
Samantha dates Jon and she can't believe how good the sex is but she too breaks it off with him after he makes a comment about the wrinkles in her neck.
Charlotte doesn't know what to do when her current boyfriend wants to have anal sex with her. She talks to Carrie, Samantha and Miranda and finally decides not to do it because she doesn't want to be known as the up the butt girl.moreless

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  • Charlotte has a boyfriend with a special request. Carrie dates twenty-something Sam. Samantha dates a twenty-something until he points out her wrinkles.

    This is one of my favourite episodes, and I have no problem saying that it is a triumph of television drama. I will never forget the 'Up the butt' conversation in the back of that cab as long as I live. So well written, I actually believe that conversation has happened to everyone at some stage of their lives. Who better to discuss this with than your single girlfriends? I think this is where men begin to grow increasingly uncomfortable with the content of the show. They cannot quite believe that women have these conversations. Well Newsflash men! They do! Most women have at least one friend who they discuss everything with. It's not that we can't think for ourselves or form our own opinions, but sometimes you just need a second opinion....or a third....

    This is also the episode where Carrie questions her 'relationship' with Big. After agreeing to an actual date, Big is at the restaurant with his recently heartbroken male friend. Carrie decides that she is better off leaving him to it and goes off to find twenty-something guy. After waking up in the apartment from hell with no toilet paper, she is walking down the street contemplating that she may have outgrown the men of her past but not quite grown into the men of her future, when she bangs into Big. I think that this is the moment when we first realise that nothing in this relationship is going to be straightforward. It's almost as if they are not meant to be together, as stuff keeps getting in the way, but at the same time we are left wanting them desperately to get it together. Carrie's comment about men being like a drug is so true. Sometimes they bring you down, but then other times they get you so high. I think that a more accurate description of their relationship has never been penned.moreless
  • Season 1, Episode 4.

    Carrie and Samantha date guys in their twenties. Carrie dates a man named Sam, and all they do is kiss, until they have sex, and Carrie realizes what his apartment really looks like: an average twenty-something's apartment with pizza boxes and dirty laundry everywhere. Samantha is dating a man named Jon, but breaks up with him after he comments on the wrinkles on her neck. Charlotte's boyfriend wants to have anal sex with her, but she decides not to go through with it. The scene in the cab was amazing. The "preview" comment was funny, and the cab driver was very entertaining.moreless
  • 20something men

    I have always liked this episode because of the cab scene with all four women, the end scene with Carrie and Big and mostly because of the horror that Carrie wakes up to after spending the night with Sam the 20something man she recemtly met. Everything about his apartment is truly frightening and very realistic which makes it even more hilarious.

    Love the fact that in the light of day Carrie is able to see that her 20something man seems to have a severe case of ADD courtesy of his rambling about his huge handed dream.

    Miranda had no storyline in this episode except to make Skipper feel bad again. I'm not as fond of Miranda during the early episodes because of her treatment on Skipper.moreless
  • Review

    Carrie and Samantha start dating guys in their twenties. Carrie dates Sam and at first all they do is kiss but it soon escalates to sex and Carrie breaks it off when she wakes up and sees his messy apartment and realizes that she's too old to date a guy in his twenties - I thought this part of the storyline was interesting because at first you think that Carrie and this guy might have something until the next morning roles around. Samantha dates Jon and she can't believe how good the sex is but she too breaks it off with him after he makes a comment about the wrinkles in her neck- Comical, but nothing more then that really. Jon wasnt that exciting of a character. Charlotte doesn't know what to do when her current boyfriend wants to have anal sex with her. She talks to Carrie, Samantha and Miranda and finally decides not to do it because she doesn't want to be known as the up the butt girl- Also comical and saved the episode for me.moreless
  • The women date men in their twenties.

    This episode was pretty good, but it definitely wasn't one of the best episodes of Sex And The City. I found the documentary parts to be pretty funny in this episode. I didn't really care for Carrie in this episode at all. I just thought that she was really annoying in this epsiode. Although, I've never really liked Carrie nearly as much as the other women. I thought that Samantha and Charlotte were pretty funny, and I think that they really stole the show in this episode. I loved Charlotte in this episode. Kristin Davis is so good at playing a prude. All in all, this was pretty good episode. It just wasn't the best episode of Sex And The City.moreless
Timothy Olyphant

Timothy Olyphant


Guest Star

Daniel Gerroll

Daniel Gerroll

Mr. Marvelous

Guest Star

Kohl Sudduth

Kohl Sudduth


Guest Star

Chris Noth

Chris Noth

Mr. Big

Recurring Role

Ben Weber

Ben Weber

Skipper Johnston

Recurring Role

Trivia, Notes, Quotes and Allusions


  • TRIVIA (3)

    • Trivia:It is revealed in this episode that Charlotte attended Smith College, which is a private university for women in Massachusetts.

    • Sam, the 20 something's tongue piercing is not real. The camera cuts to a shot of someone else's tongue piercing.

    • In this episode Carrie receives a phone call from Samantha and her voice over says she needs her morning Marlboro Light, however, when she picks up her pack of cigarettes, you can see that it is a pack of Merits.

  • QUOTES (17)

    • Carrie: Once upon a time in a kingdom faraway, a certain man and a slightly less certain woman kept bumping into one other. They seem to meet everywhere; on street corners, at parties. It was almost as if they were dating accidentally. And then, after another chance meeting, at a wealthy lawyer's new son's bris, they decided to pick a time to bump into each other on purpose.

    • Carrie: Alright, so officially he's late.
      Charlotte: Who?
      Miranda: Mr. Big, who else?
      Charlotte: Carrie, that's great! Is it a date?
      Carrie: No he called it a "thing". He said, meet me for a drink "thing". He never used the "d" word.
      Charlotte: Well, "thing" is good. I mean, "thing" comes before date.

    • Mr. Big: I've been looking all over for you - here you are. Holding a tongue.
      Carrie: Well, your message said you weren't coming.
      Mr. Big: I thought I said I'd try to make it for an hour.
      Carrie: Well, yeah, but then you said that...
      Mr. Big: What? What did I say?
      Carrie: Never mind, never mind. You're here, you have an hour, let's have a drink.
      Mr. Big: Well, I was outside trying to get in for 30 minutes, inside looking for you for 20 minutes so that leaves me with just enough time to tell you that I'm out of time. You have fun.

    • Sales Guy (to Carrie and Twenty-Something Sam, who were making out in a Banana Republic dressing room): Please. This isn't the Gap.

    • Carrie: Meanwhile, uptown, Charlotte wondered when relationships had gotten so complicated. She yearned for the time when dinner was followed by dessert, not lubricant.

    • Carrie: I decided, the only way to break free was to move from one addiction, to an even bigger

    • Carrie: I realized I had just entered an interesting chapter in my life. I had outgrown the boys of my past, and not quite grown into the men of my future.

    • Carrie: Same time, same place, just you and me.
      Big: Well, sort of. Meet my friend Jack.
      Carrie: Oh, hi, how are you?
      Jack: Marvelous. Going through my second divorce. Bitch is getting everything the first bitch didn't.

    • Charlotte is trying to decide whether to have anal sex with a man she's dating.
      Miranda: It all depends on how much you like him?
      Charlotte: A lot.
      Miranda: "Dating a few months until somebody better comes along a lot", or "marrying him and moving to the East Hampton's" a lot?
      Charlottte: I don't know, I'm not sure.
      Miranda: Well, you better get sure real quick.
      Charlotte: You're scaring me.
      Carrie: Don't scare her.
      Miranda: It's all about control. If he goes up there, there's gonna be a shift in power, either he'll have the upper hand or you will. Now there's a certain camp that believe whoever holds the dick, holds the power. (Cab Driver turns around) Hello, you're driving! The question is, if he goes up your butt, will he respect you more or respect you less? That's the issue.
      Cab Driver: No smoking in cab.
      Carrie: Sir, were talking "up the butt", a cigarette is in order.
      (Cuts to Samantha now in the cab)
      Samantha: Front. Back. Who cares? A hole is a hole.
      Miranda: Can I quote you?
      Samantha: Don't be so judgmental. You could use a little back door.
      Charlotte: I'm not a hole.
      Carrie: Honey, we know.
      Samantha: Look, all I'm saying is this is a physical expression, that the body, well, it was designed to experience. And p.s., it's fabulous.

    • Carrie: So, then what's really going on here? Do younger men feel safer?
      Miranda: What's really going on here is sex. Good old-fashioned, eager to please, do what I tell you to, Eagle Scout sex.
      Carrie: But, I'm not having sex. It's a kissing thing.
      Miranda: So, what's the big deal? It's just a fling. It's not like we're throwing out our schedules or anything.

    • Carrie: Shouldn't we be dating men our own age?
      Miranda: Good luck finding one. There are no available men in their 30's in New York, Giuliani had them removed along with the homeless.

    • Samantha: (on the phone) I am so fucked.
      Carrie: What's wrong?
      Samantha: No, I mean, literally. I have been fucked every way you can be fucked.
      Carrie: If you keep talking like that, I'm gonna have to charge you by the minute. (goes to a voiceover) As I searched for my morning Marlboro light, Samantha proceed to give me a rundown of her night with Jon--no "H", no inhibitions. (voiceover ends)
      Samantha: We did with him on top, me on top, me on my side.
      Carrie: Him on his side?
      Samantha: Oh, God, yes. On his back, on his side, on his face. Have you ever done that?
      Carrie: It's too early to remember.
      Samantha: Well, do it immediately. It is fabulous. These guys in their 20s, they are up for anything. How did it go with you and Sam?
      Carrie: We kissed.
      Samantha: Just kissed?
      Carrie: No. We just kissed for five hours - at the club, in front of the club, on the corner of the club. I forgot how much fun it is to just kiss, you know, even if I did only get two hours of sleep.
      Samantha: I didn't sleep at all.

    • Carrie: Men, in their 40's are like the New York Times Sunday crossword puzzle; tricky, complicated and you're never really sure you've got the right answer.

    • Skipper: They stopped making Martinis, so I got us two rum and cokes. Is that okay?
      Miranda: Well, I hate rum, and I hate coke, but, thanks.

    • (listens to a message from Big on her answering machine)
      Carrie: Oh, something came up he's not gonna meet me. Here, will you listen to this and tell me if you can figure out whether he's not meeting me as a date, or not meeting me as a friend?
      (Miranda takes the phone)
      Miranda: Alright.
      Carrie (voiceover): Sometimes, you need a second opinion; with doctors, real estate, men.
      Miranda: I have no idea. And I finished first in my litigation class.

    • Miranda: Where did Skipper go?
      Charlotte: I don't know how you can date that younger guy? I mean, they're so scattered and unfocused.
      Miranda: We're not dating, it's a fuck thing.

    • Charlotte: I don't know what I want. But I'm afraid if I don't you'll dump me. And if I do then I'll be up the butt girl. Men don't marry up the butt girl. Whoever heard of Mrs. Up The Butt?

  • NOTES (1)