Sex columnist Carrie Bradshaw and her close friends navigate the complex world of dating in New York City.

Miranda discovers she was invited at Nick's, where all guests are asked with which movie star in the prime they would have loved to do it, to make a change with all those brainless models he keeps dating. The girlfriends see models as a living nightmare as those terribly demanded competitors actually walk around in Manhattan, giving them socially imposed inferiority complexes, except man-eater Sam. Carrie's friend poor painter Barkley, a serial 'modelizer', treats models as things and secretly videotapes his sex with them; Sam sees him as a challenge for her as superior non-model, and even insists to be taped. Stanford introduces Carrie to his friend and best client, gorgeous underwear-model Derek 'The Bone', who actually asks to stay the night with her and is even more shy and lonely then mortals who crave models, wanting to become a cop in his Iowa home town.

Carrie and Mr. Big keep bumping into each-other till they date (without that term) at Samantha's hot restaurant PR-opening, but he cancels last minute. The cook, just Jon, is reserved for Samantha's bed, but his hot friend Sam, also twenty-something (those always seem to know the right people) flirts with Carrie; Big turns up saying he was on time but couldn't find her, time to leave town. At a twenties club Sam takes Carrie on his lap and kisses really well, five hours long, and again while she helps him pick a shirt. Samantha eagerly reports on a night of sex with Jon, twenties-men are so hot and consider thirties-women a good deal. Charlotte is embarrassed Bryant explicitly asked for anal sex, Miranda warns her not to give in on respect which is power, Samantha says a hole is just that; Charlotte gets a decent first date. Samantha realizes she'll always feel older with twenties-men, and resolves to give them up. After Big brought his just divorced friend Jack to their drink, Carrie seeks consolation in Sam's bed, in heaven when spooned, only to wake up in his nightmare apartment which comes with a room mate, but no toilet paper, and runs off to her ultimate addiction- the shoe store.

While shoe-shopping, Carrie meets Amalita and her new rich boyfriend. Amalita's life is full of vacations, holidays, and shopping with very rich men. Over dinner, she introduces a young, handsome architect to Carrie. Her evening ends at his luxurious hotel. Waking up, she finds that the man has left her a considerable sum. Appalled, she calls up her friends and they discuss the power of sex. Meanwhile, Charlotte is asked to model for an artist who is doing a series of paintings of vagina.

When she discovers that Big is dating other women, Carrie realizes that she desires a monogamous relationship with him. In the meantime, Samantha is having trouble being monogamous with her realtors. Charlotte dislikes the sexual desires of her new boyfriend, and Miranda confronts jealousy when she runs into Skipper with his new girlfriend from Vogue.

Miranda dates rising playwright Thomas John Andersen, whose only flaw is he needs to shower immediately after sex, which he blames on nun teachers; her uttering sex is not sinful gets her thrown out forever. Carrie observes churches draw classy dressers- as her Mr. Big, an atheist who takes his Presbyterian mother every Sunday and won't invite Carrie along. Samantha startles telling she's in love with jazz-loving lawyer James, without having had sex; when they finally do, she can't even feel his tiny cock, she's shattered and hates herself for it. Charlotte consults psychic card-layer Noanie Stein who sees no marriage for her, so she tries Santeria, where she's told that's curable for $300. When Carrie spies on them with Miranda, Big is not amused, she desperate that he introduces her as just a friend. Stanford invites everyone, even Skipper, to the gay disco club presentation of the new fragrance Fallen Angel and his boyfriend Allanne, the bottle designer. Carrie expresses her doubts when Big comes pick her up for a holiday trip- couple canceled.

Carrie meets Miranda's ex Skipper, a sweet guy who is getting desperate as all women seem to turn him down in favor of jerks - like Kevin, the bossy colleague Miranda is dating right then. When she confesses this to her friends, this contradiction bugs her too. Sam declares monogamy fits none of them, as its high expectations are never met. To everyone's surprise, Charlotte takes that advice to the extreme, double-dating two fine men - till they find out and walk out on her together. After a few lonely weeks without Big, Carrie invites John, her dependable rebound-lover just-for-sex who always repairs her self-esteem, and wonders why she never tried committing to him, so the next time they actually go out for dinner, which only proves their conversation is as uninspiring as their sex is enjoyable; the following movie is their last date ever.