After Carrie's break-up with Mr. Big, despite Charlotte's rule it takes half the duration of a relationship to get over it, she lets true fan Miranda take her and Sam to the Yankees stadium, where she accidentally catches a ball and thus meets and invites, to everyone's surprise with success, charming baseball star Joe Starr to a party but bumps into Big there. Samantha is still miserable and tries to physically coach her James in bed, to no avail. Charlotte finds a lover with only one drawback, instinctive reaching for his balls, and buys him boxer shorts - which he finds too possessive.

As Carrie's birthday approaches, she finds herself at the center of a friend's domestic drama, while Samantha faces the truth, Miranda has an awakening, and Charlotte seeks solace in a new male.

Carrie ponders the theory that all Manhattan men are freaks. After Samantha found out an eligible lawyer has a masochistic closet, she decides too cheer up herself by scheduling having her fanny's fat injected in her facial cheeks. When Carrie meets charming journalist Ben, she doubled-dates with his mate Luke and Miranda - a total misfit because she abhors his position that nothing outside is worth leaving Manhattan even for a holiday. Charlotte meets the legendary Mitch(ell) 'pussy' and experiences he never disappoints in bed, but can she really be satisfied without an actual relationship? Meanwhile Carrie gets freaked out by her failing to find Ben's freaky side, so she takes drastic action at his place.

Now none of the girls has a relationship, the quartet hits a salsa bar all night, so Carrie is late for a photo-shoot for Stanford's boyfriend Nevin's magazine; the result is worse then she ever feared. Only Samantha is absent from the power-walking, where Miranda bumps into an ex, hunky ophthalmologist Josh, who just didn't give her orgasms; history repeats itself, and she still fakes coming; once she tells him, his confidence is shaken, so he gets her to coach him- now sex feels like an exam subject. Charlotte enjoys the handy jobs done by and kissing with unemployed actor Tom, too much to see him move to Salt Lake City for a soap part, but is that enough? Samantha was picked up by the salsa club's co-owner William, and invites Carrie to join them for the summer in the East Hamptons, but is stood up. At a party with Stanford, drunk Carrie meets single smoker Jake.

Carrie and Charlotte reproach Sam for wearing bright clothes to designer Javier's funeral, but it turns out their black clothing sticks out instead. Having solicited clients for her PR business there, Sam jumps the bones of the 'right' man, but when his all-too-influential wife walks in on them, her vital social acceptability is endangered. Charlotte meets hunky young widower Ned and enjoys helping him overcome his grieving in bed, until she discovers she isn't the only one. Miranda's pride when she buys her first apartment is short-lived, as the paperwork seems to stigmatize her "single woman" status. Carrie calls Big again after six months and finds out just going bowling revives their relationship completely.

While Charlotte has a great sell in the gallery, especially to 'power lesbians', Samantha spots her hunky gym instructor Thor, and soon has him showering with her and enjoys his creative shaving of her pubic hair, but is this really original? Carrie sneaks out to her date with Mr. Big without her friends noticing. Miranda dates a pretentious documentary movie buff, but is less and less comfortable with his insistence to 'get in the mood' by watching porn while they make love. Charlotte, who found her current boyfriend kissing another in the gallery, decides to go out 'man-free' with the lesbians, but can she really fit in?

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...

After 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?

The girls wrestle with the question how and if partners can/want to change for each-other. For Miranda this means fitting her busy schedule to lover Steves late hours as barman and cuddling appetite when she wants to start the working day. Carrie wants to stop Big ogling other women and other 'little' things. When Charlotte decides her uncircumcised lover, restaurant critic Mike, looks like a sharpei below the belt, he decides to everyones surprise to get cut, but the psychological side-effect of his 'second virginity' makes her regret his move. Samantha is happy being the flexible one, but it rattles even her to meet a former lover who had a sex operation and renamed himself after her.

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.

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?

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.

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.

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.

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.

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...

The 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.

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.