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Sex and the City: Valley of the Twenty-Something Guys

Carrie and Samantha both date men in their twenties but both break it off after they realize they're too old to date twenty-something guys. Charlotte gets advice from Carrie, Samantha, and Miranda about whether or not to have anal sex with her boyfriend.

Episode Info  

Episode number: 1x4
Airdate: Sunday June 28th, 1998

Guest Stars
Chris NothChris Noth
As Mr. Big
Daniel GerrollDaniel Gerroll
As Mr. Marvelous
Andre VippolisAndre Vippolis
As Underage Guy
James A. Wolf, JrJames A. Wolf, Jr
As Corporate Guy
Michael ParrMichael Parr
As Groovy Guy
Robert SteinmanRobert Steinman
As Salesman
Upendran PanickerUpendran Panicker
As Cab Driver

Kenneth Keith KallenbachKenneth Keith Kallenbach
As Sam's Roommate
Michael Cline (1)Michael Cline (1)
As Man in Elevator
Episode Quotes
Miranda: There are no available men in their thirties in New York. Giuliani had them removed along with the homeless.

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

Charlotte: I'm afraid if I don't, you'll dump me, and if I do, then I'll be the up-the-butt girl. And I don't want to be the up-the-butt girl because, I mean, men don't marry the up-the-butt girl. Who's ever heard of Mrs. Up-The-Butt?

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?
Charlotte: 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, your 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 here, a cigarette is in order.

Carrie: And just when I thought it couldn't get any better, he spooned me.

Carrie: 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.

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

Carrie: Same time, same place, just you and me.
Mr. 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.

Samantha: 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.

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.

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: 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.

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.

Episode Goofs
When talking on the phone with Samantha, Carrie's voice-over states that Carrie needs her early morning Marlboro Light. However, the pack of cigarettes next to her are Merits.

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