The four friends take the ferry out to Staten Island to watch and judge the New York City Fire Department's "Calendar Contest". Carrie meets a handsome local politician, Bill Kelley, but is reluctant about starting a relationship with him. Charlotte decides to get herself married by the end of the year, and has a date with Arthur. Samantha meets Ricky, a dream hunk, but their time together is ended prematurely when he has to leave to attend a fire. Miranda realizes that being rescued isn't necessarily a sign of weakness.
Carrie eventually consummates her relationship with Bill Kelley, but is put out when he reveals a fantasy of his. Charlotte starts to put into action her plan of getting married by the end of the year, by throwing a 'used-boyfriend" party. Samantha meets a bachelor, who although he is no match for her in height, is a match between the sheets. Miranda discusses with Steve whether their relationship should become deeper.
Carrie spots Mr. Big and Natasha's wedding announcement in the paper, and later bumps into her while shopping. Samantha treats the four friends to a day at a spa, where one of the male attendants is reputed to give more than just massages. Charlotte is inhibited about disrobing in the steam baths, but later manages to force herself to, and is pleasantly surprised. Miranda has a new, Ukrainian cleaning lady, Magda, who takes it on herself to clean up Miranda's life as well as her apartment.
Carrie finds out that Sean, her new young boyfriend, has had relationships with both men and women, and tries not to let it faze her, but it does eventually. Charlotte takes part in a photo shoot by a famous photographer, Baird Johnson, whose latest technique is to photograph women dressed as men. Samantha stands up to Matt, her new male assistant, eventually firing him, and then having sex with him. Miranda begins to feel suffocated by Steve's presence in her apartment, but when he leaves she feels lonely, and ends up inviting him to move in.
Carrie tries to quit smoking to improve her chances with her new boyfriend, Aidan Joff, a furniture designer. Charlotte has a new boyfriend, Brad, but he turns out to be an irredeemably lousy kisser. Samantha dates Chivon, an African-American, but his sister is no so open-minded. Miranda doesn't have the time to watch Steve practice basketball, even though there's the potential to win a million dollars: he is upset about this, and she realises she needs to put more effort into their relationship.
Carrie wonders why Aiden won't sleep with her even after a romantic bath together. But Carrie finally realizes that she's gotten used to skipping romance and having sex right away. Alexander Lindley, Charlotte's new boyfriend, talks too much while in bed, upsetting Charlotte. Miranda contracts an STD and has to let her previous boyfriends know that they might have an STD as well. Meanwhile, Samantha is forced to move when she's blamed for letting in a man who robs a resident at gunpoint.
Carrie is invited to meet Aidan's family, but she feels overwhelmed and declines: she then spots Mr. Big and Natasha out together, and comes to realise that she has been behaving badly, and decides to meet Aidan's family after all. Charlotte falls down in the street and meets Trey McDougall, a very eligible doctor, with whom she hits it off immediately. Samantha is seeing Mark, a doctor with access to a supply of Viagra, which she experiments with. Miranda gets used to the details of a life of domesticity with Steve.
Carrie keeps bumping into Mr. Big, causing her to wonder what's going on, which she finds out when he confesses he can't stop thinking about her. Charlotte starts to think that Trey might indeed be her "Mr. Right". Samantha fears she is becoming menopausal, but when sleeping with Len, an older man from her new apartment building, discovers she's not. Miranda is starting to get fed up with living with Steve, and the last straw comes when he tries to persuade her it's time to start thinking about a baby: they break up.
After Mr. Big confesses to Carrie that his relationship with Natasha is not going well, they return to their old ways, resulting in a night of passion. Charlotte realises her greatest goal in life when she and Trey become engaged, though it was she who had to pop the question. Samantha has a difficult time with Adam, her latest boyfriend. Miranda and Steve are still sharing an apartment even though they've broken up, and they find out that it's not easy living with a former partner, particularly if they want to date someone else.
At last Aidan says that he loves Carrie, which makes her feel even more guilty about her renewed relationship with Mr. Big. Things go well with Charlotte's engagement to Trey, until he proposes a prenuptial agreement that upsets her. When she's feeling down with the flu, Samantha panics that she's going to end up alone, as no-one is prepared to look after her. Miranda finds that phone sex (with her new boyfriend George) can be as fulfilling, but also as painful, as more usual relationships.
Carrie's reignited affair with Mr. Big puts a increasing strain on her relationship with Aidan, and she meets Natasha again in the worst of circumstances: while letting herself out of the Bigs' home. In the commotion, Natasha has an accident, so Carrie takes her to hospital. Charlotte becomes more and more preoccupied with preparations for her wedding, especially finding the perfect wedding dress; she also finds out about Carrie and Mr. Big, and is outraged. Samantha's new boyfriend, Tom Reymi, makes her have an AIDS test, which fortunately proves negative, before he will sleep with her. Miranda is attracted to a man wearing a sandwich costume.
Carrie is in a continued quandary as to whether to tell Aidan about her renewed relationship with Mr. Big. At the last moment, Charlotte starts to have doubts about marrying Trey. Samantha has a relationship with one of the wedding party. Miranda pretends to be an air stewardess to get a date.
At short notice, Carrie, Samantha & Miranda go to Los Angeles, so Carrie can discuss options on making a movie based on her columns. Her agent Debbie sets up a meeting for her with Hollywood actor/producer Matthew McConaughey. Samantha meets an unusual sort of model at a party. Miranda takes a wild ride on a mechanical bull, determined to enjoy herself. Meanwhile, Charlotte has been on a sexless honeymoon in Bermuda, and tries to find out what Trey's problem really is.
Carrie, Samantha & Miranda spend a second week in Los Angeles. Carrie & Samantha go to a movie screening party, but are refused entry at the door. Fortunately another guest, Keith Travers, gets them into the party, and Carrie spends the evening with him, ending up in bed at his fabulous home, until she discovers he isn't all he pretends to be. Miranda meets up with Lew, an old friend from New York, and finds he's mellowed since he's been living in LA. Charlotte despairs of her sexless marriage, and flies to LA to be with the others.
Carrie meets a new man, Wade Adams, at a comic store, and falls in love with his fabulous apartment, but not with his mother. Samantha is hired as the publicist for the Bat Mitzvah of Jenny Brier, and finds that Jenny and her friends are as over-sexed at 13 as Samantha is at 34. Charlotte searches the internet for a solution to Trey's sexual problem, and then demands that they see a sex therapist. Miranda is having to wear braces, which make her feel like a teenager, but she gives them up after a date fears he'll get caught up in them.
When Miranda's date fails to show up, she calls him but finds out that he died the night before. At the wake, Miranda hits it off with one of Carrie's ex-boyfriends despite Carrie warning her about him. Carrie speaks at a seminar about meeting men but the cynical audience ask her pointed questions and begin see that she's not suited to teach the seminar. Samantha befriends Claire Ann, who she thinks is her equal until Claire Ann takes flirting with a man too far.
Carrie is snubbed by Natasha at a restaurant, and is then mugged. Samantha drags Carrie to a party, only to find out it's a dorm party; Samantha makes out with one of the college lads, who happens to share the same name with her, but he becomes obsessed with her. Charlotte, tiring of the lack of sex with Trey, has a couple of encounters with a gardener, which leads to their separation. Miranda has a date with the police detective investigating Carrie's mugging, but nervous that she isn't good-looking enough, gets too drunk.
Mr. Big phones Carrie and invites her to lunch, which she accepts against Miranda's advice. Samantha's sleep is being disturbed by the noise made by some transsexual prostitutes, and she ends up inviting them in for a rooftop party with the other three friends. Charlotte receives an early-morning visit from Trey, who's finally ready for her. Miranda is feeling that her life is in a rut, and runs into Steve on a couple of occasions.