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- Four female New Yorkers gossip about their sex lives (or lack thereof) and find new ways to deal with being a woman in the late 1990s.
- The lives of several individuals intertwine as they go about their lives in their own unique ways, engaging in acts which society as a whole might find disturbing in a desperate search for human connection.
- The girls worry about long-term change. Miranda hears from her gynecologist that one of her ovaries is 'lazy', and worries therefore is she can still take her time being picky with men before going for motherhood. Charlotte hits on well with charming pastry chef Stephan, but consults the girls and guy friend Stanford if he is gay, or at least 'half'. Carrie worries if Big is serious about them since he seems too 'territorial' to allow any of her stuff permanently in his apartment. When Samantha sees publisher Dominic, the one man who broke her heart for a model, she decides to turn tables on him, but can she really dump him 'like a man' after great sex?
- Three of the girls deal with loved ones from their past. For Carrie it's trying to become just good friends again with Mr. Big, who now is with Natasha and even tells her they are already engaged. For Charlotte it means the pony Taddy which threw her off as a child, or a substitute horse. For Miranda it's becoming friends again with barman Steve, but then they get physical again... Samantha however finds by chance a new, huge hunky man who seems about as cocky as she is, and proves he has a cock of matching (record) size which even she may not be able to handle.
- When even her friends are sick and tired of Carrie's raving after the break-up with Mr. Big, she takes their advice to go to therapy, as everybody does in Manhattan, and gets a surprise bonus: in the waiting room she meets Seth, who proves a substitutive therapy in the flesh. Samantha picks up a man in a sports bar, but will even she ever get his full and undivided attention for nonathletic practice? Miranda feels really flattered when a gorgeous man in the adjacent building goes from flirting to stripping at the window, but when she meets him learns his eye is on a male tenant one floor below hers.
- Big tells Carrie that he's moving to Paris for six months; Samantha introduces the girls to the hottest new S&M restaurant; Charlotte's shoe fetish is counterbalanced by a shoe store foot fetishist; Miranda meets a guy who likes to "do it" only when he thinks he might get caught.
- Miranda considered Sunday a nightmare because children swarm everywhere, there is even a family hour at her gym, but it did allow her to meet hunky Simon Cobb, indulgent divorced father of rascal Simon, who loves to push the elevator's buttons, and his; when Simon surprises her naked in the lo after a hot night, that signs her marching-orders. Carrie met fiction writer Vaughn Wysel at a lunch; he presents her to mother Wallis, her partner Duncan, a teacher, and sisters Franny and Zoe, who all insist she stays for a seafood feast; six hours later he can finally jump her bones, yet his sperm beats him to the post. She keeps dating and doing him for his whole family, mainly the fascinating mother, an Oscar-nominated documentary maker, despite his recurring precipitous wetness, but precisely her liberating education without sexual taboos proves unsurmountable. Charlotte receives her studly brother Wesley, about to be divorced from Lesley; he tickles Samantha's fancy at first sight. Charlotte explodes finding Sam in her guest-room wearing only his T-shirt, but when Wesley explains he needed the sex after two sexually frustrated years with his frigid wife, Charlotte goes make up.
- The girls wrestle with social inequalities. When Samantha dates super-rich Harvey, she enjoys the perks she claims not to crave, but finds his relationship with female servant Sum is not as one-sided as it seems. Charlotte's date with celebrity actor Wylie Ford starts as a luxury dream, but she soon finds she's expected to become more of an abjectly servile fan then a self-respecting lover. Miranda takes Steve shopping for his wardrobe but has a taste he cannot afford and yet won't allow her to pick up the bill, even if that breaks them up. Carrie is insecure again when Big takes her to a socialite party on Park Avenue but never seems able to express his love, and therefore she goes out with an artistic flirt without means she find waitering there.
- When Miranda's friend Jeremy Fields, a reporter in London who is often flirtatious in their e-emails, visits New York Miranda is happy to put him up - however he proves more flirtatious with a local friend of hers who just decorated her apartment, and at the farewell party she throws for him even announces their upcoming wedding! The friends have mixed feelings being invited, three of them rather commandeered in various capacities. Miranda feels the invisible woman, 'in charge' of the self-explicative guest-book; Sam feels her Manhattan life is ending when she realizes she slept with a man she already had some 15 years ago; Carrie goes from a high when Mr. Big accepts to accompany her to the wedding to hear her requested occasional poem to a low when he declines signing the card with their wedding gift and leaves during her recitation for a business call; bridesmaid Charlotte is tickled pink she finally may choose herself a gorgeous dress and team up with eligible best man Martin Healy, but when he actually presents her to his parents...
- 1998–200430mTV-MA7.8 (885)TV EpisodeAfter walking out on her date who turned out to be still married despite his claim to be divorced, Miranda is happy to be picked up by cocky barman Steve, who soon wants more then their one-night stand. Carrie believes her rekindled relationship with Mr. Big is good enough to get him to know her friends a little better. Samantha has an atypical lover, even for a man-eater like her: Donald Trump's single friend Ed is past 70, so will his old-fashioned wooing and lavish gifts outweigh his physical decay?
- 1998–200430mTV-MA7.9 (834)TV EpisodeThe girls wrestle with the onslaught of 20-something girls when they are invited to a beach party in the Hamptons. Charlotte suffers a nasty punishment for passively lying about her age: her even younger toy-boy Greg gives her crabs. Sam fires her assistant Nina, only to find she is hosting the A-list party in the Hamptons using Sam's contact list. Carrie has an eager young writing admirer in Laurel and a bigger admirer in doctor Bradley Meego. Her weekend is ruined, however, when she finds Mr. Big there, back from Paris, with a new 20-something girlfriend, Natasha.
- Charlotte panics about her 'bed-manner' when her lover Dr. Bram Walker dozes off in bed once after a grueling day of surgery, so she takes a tantric sex class given in a very hands-on demonstration by a psychologist couple. Sam not only proclaims the dawn of pan-sexuality, but actually agrees to have a threesome with gay couple David and David, who lose interest in the idea just when she was running hot. Carrie bumps into (the cigarette of) very cute film composer Patrick Casey. She is puzzled how reluctantly he takes further steps until he confesses to be a recovering alcoholic, but when she is the one hitting the breaks...
- Carrie feels guilty as hell about sleeping with Big behind Aidan's back, but re-offends when he's out of state; while Big announces he wants to leave his wife for her, she loses Aidan's dog, Pete. Charlotte's engagement-bliss withers when Trey's family's 'standard' prenuptial appears. Just after boasting how much better life is without a steady man, Sam experiences it's no fun being single with the flu. Miranda is very happy with a young new colleague, having a one nightstand followed by long-term phone-love as he returns to Chicago- till she finds out...
- Carrie can't understand why Aidan doesn't want to sleep with her, and then feels jaded when she finds out that Aidan doesn't go for sex for the old-fashioned reason he is still romantic. She wonders if modern Manhattan girls like her are just sluts, and is he serious, or, as Samantha suggests, becoming just a friend? Charlotte has a great lover, a gentle gentleman, with one flaw: without knowing it, he calls her a bitch and whore during sex; when she tells the poor boy, he's as horrified as she, and struck impotent. Miranda discovers she has chlamydia, so she calls all her 42 former partners, and Steve suffers an intimate test despite being monogamous. One of Samantha's countless dates accidentally allowed a violent robber into her posh building; as soon as the other tenants find out, she feels shunned...
- 1998–200430mTV-MA7.5 (713)TV EpisodeCharlotte gets depressed just by reading all women in "The New York Times" Sunday edition wedding announcements are younger than our quartet, but stumbles on Carrie's nightmare: Mr. Big's marriage to Natasha - her answer is to spend a fortune in order to outshine the bride to be. Miranda's new cleaning lady, Magda, makes her feel guilty not to be more of a housewife and for having sex toys. While Charlotte feels nasty just being naked in an all-female health spa, Samantha books an extra massage when told Kevin also gets intimate, but ends up being thrown out for taking the initiative.
- Carrie finds out the guy she is dating is bisexual, and because of him, she explores the bisexual community for the first time.
- Carrie and Samantha deal with noisy neighbours, and Miranda fears that the takeout lady laughs at her for ordering for one.
- When Miranda tries multi-dating, she quickly finds nobody wants a lawyer, while her same physique appeals as a "stewardess". Things get interesting for her when she decides to date a doctor - At Charlotte's rehearsal dinner, Samantha hooks up with Trey's cousin Caleb, even if she can't understand his Edinburgh accent. Carrie is touched that Aidan created a love-seat as a wedding gift for her friend Charlotte; finally she gathers the courage to confess her infidelity with adulterer Big - Charlotte has a sleepless night before her wedding after sleeping with Trey for the first time.
- Miranda and Steve are finally feeling comfortable together, until she watches the laundry. Samantha has hot nights with a doctor, and decides to follow his example taking Viagra purely for recreational purposes. Charlotte is inspired by a book to start looking for a fiancé more methodically, and commandeers a wedded friend of hers, allegedly the ideal ally, to tell his friend Phil he is supposed to become her dream date - when he stands up the all too eager would be-bride at the opera, she goes with Carrie, who was just getting comfortable with Aidan but suddenly crosses glances with Mr. Big.
- Now that Miranda and Steve have fallen out of love over parenthood, they painstakingly live apart in the same flat... At Aidan Shaws's design fair, Carrie bumps into Mr. and Mrs. Big. Later, a drunken Big blurts out to Carrie that he not only wants a divorce but also wants her back. Then, when Aidan generously starts improving her apartment, the noise drives her to a hotel... Charlotte is convinced Trey is ready to propose and is presented to his mother Bunny MacDougal. She seems to control him masterfully. Later, Charlotte uses Bunny's sleeve rubbing trick and makes him thoughtlessly accept a wedding proposal by her. She instantly regrets it because it lacks the romance she desires... Sam likes giving blow-jobs, but her present lover, Adam Ball's sperm tastes really bad.
- Miranda thinks she's been stood up until she finds out her date died of a heart attack. She agrees to go to the wake, where she meets a great guy who used to date Carrie, who warns Miranda he has a nasty side. When Charlotte tells her friends Trey is now sexually interested in her but still can't perform, Samantha convinces her it's a classical Madonna-whore complex. A meeting with Charlotte's sorority sisters has the frustrated Charlotte determined to transcend her prudish outlook. Samantha finds her sexual equal in a woman named Claire Ann, whose wild behavior shocks even Samantha. Carrie agrees to teach a class on dating at the local learning annex, only to realize she doesn't know as much as she thinks.
- 34-year old Miranda feels a teenage girl again when her dentist gives her braces. Samantha is jealous of a 13-year old, super-rich client, who seems to have skipped the teen years altogether. Carrie's gorgeous younger boyfriend Wade "Superboy" Adams is a comics-shop-clerk who makes her feel young again, as they do teen- and tween-things together, or perhaps too young: he still lives with his devoted parents... Meanwhile Charlotte resorts to heavy medical therapy for Trey's sexual non-performance, and gets surprising results.
- Carrie is attracted to a furniture maker named Aidan and starts dating but he can't date a smoker. She must decide on Aidan or smoking. Charlotte attempts to coach a bad kisser while Miranda finds difficulty in supporting Steve's pipe dream of making a half court shot at the Knick's game. Samantha begins dating an African-American record executive who has a strong-willed sister who runs a new restaurant.
- Carrie shares her bed and his campaign for city treasurer with Bill Kelley for weeks and Sam has a short lover.
- Charlotte's wedding planning panic is easily solved when Sam refers her to gay stylist Anthony Marantino, 'the Italian mother she never had'. Paranoid Miranda worries about a 'scary' man in a restaurant's sandwich-suit saying "eat me" in a 'woman-unfriendly way'. When Samantha finally meets her male sexual counterpart Tom Reymi, eagerness to 'do it' in his swing makes her overcome an old pathological fear for aids-tests. Carrie is torn between sweet Aidan and exciting adulterous Big who wants to come out, but when Natasha returns early...