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 is invited to stay with a married friend and her husband, Peter, at their beach house. Her trip is unexpectedly cut short when she walks in on Peter who is naked in the kitchen. Back in Manhattan, she contemplates whether there is a secret war going on between the singles and the married. Later on, she is introduced to a guy who's desperately trying to start a family. It seems that dating the marrying-type guy has suddenly made her a member of a club for married couples.

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.

Carrie put asides her misgivings about a photo session for a promotional picture for her columns, to go on buses, because she was allowed to keep the sexy dress, which she wears on her first 'official' dinner date with Big, and has sex against Charlotte's Victorian restraint rules. Her friend Mike Singer found an ideal sex-partner in sales clerk Libby Biyalick, but prefers to keep the affair discrete as she wouldn't do as life-partner; Carrie realizes and resents being Big's, till she confronts him. Miranda meets 32-year old sports doctor Ted Baker by punching him in gym class, they become fine sex partners, but when he learns she found in his flat his secret passion, spanking videos, which the other girls regard quite differently, he walks out for good. Charlotte recalls her Chassidic ex-lover Shmuel, an artist.

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.

Architect and amazing lover Jack, an ideal catch for princess Charlotte, whom she met at many disease benefits, strongly suggest a trio with another woman- the friends are divided if or how. Samantha does it with married 37-year old wine importer Ken Shear; when he tells his wife Ruth, she insists Sam participates in his fantasy, a threesome, to save her marriage. Carrie is surprised nearly everybody has trios, and startled Mr. Big is divorced, from publisher Barbara, who proves a great lady and even interested professionally in Carrie's on the spot invented novel theme -intolerable, as if she were in bed with her and Big- and tells he was the cheater! Irritated to be the only one not asked for a trio by a friend, Miranda answers a couple's threesome ad.

After Samantha is dumped, she tries to turn 'The Turtle' into a catch.

The girls attend a baby shower for their formerly hard-partying friend Laney, which leads each of them to reflect on where they are in their lives.

After weeks sharing a bed, Carrie feels comfortable actually sleeping with M. Big, yet mortified when she farts in bed, but really worried when he stops to want sex every night. It really hits her when he prefers to watch a boxing match to kissing, so she paints her apartment. Miranda tells Carrie to be herself and feels she's worse off not having had anyone for three months, but how often is normal? Samantha is horny for her hunky yoga instructor Siddharta, who claims to practice Bhramacharya, Tantric celibacy, since three years, yet still gets hard-ons. Charlotte tells Carrie to be happy her boyfriend Kevin didn't even kiss in three weeks, takes it as an aphrodisiac that he's Carrie's ex from three years ago and a sex maniac, but then learns he has given up sex to cure his former bad temper by Prozac, indeed even a hand-job has no result. Carrie's neighbors, who frequently have amazingly long, naked sex in front of the open window, are a spectacle for the envious quartet- and inspire Mr. Big...

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.