Carrie dates a twenty-something man who's openly bisexual. Miranda deals with personal issues when Steve proposes moving in with her. Charlotte poses as a drag king for an artist at her gallery. Samantha butts heads with her new twenty-something male assistant.

Carrie and Mr. Big begin dating on a regular basis, but she learns after bumping into him that he is dating other women. Samantha begins to look for an apartment to purchase.

Carrie starts seeing Mr. Big again. Miranda buys her own apartment on the Upper West Side. Charlotte meets a recent widower at a cemetery. Samantha's actions with a married man gets her in trouble with the New York high-society "ladies who lunch" and only a titanic star can help her out.

Carrie meets a jazz musician while on a pseudo-date with Big. Miranda tries to get more comfortable using the bathroom in front of her date. Charlotte is dismayed that Trey only wants to have sex in places where they can get caught. Samantha meets Maria, a lesbian painter, at Charlotte's gallery, and questions her own sexuality.

Carrie continues to date Ray King, the jazzman, but finds he has an ADHD problem. Miranda substitutes chocolate for sex. Charlotte deals with Trey getting a little too overconfident in bed. Samantha tells the girls she's in a relationship with Maria and is now a lesbian.

After Berger flips out and flips off his ex-girlfriend's answer-phone message, Carrie tries to not think about her influence on his life. Miranda finds condoms in Brady's diaper bag and gets upset with Steve. Newly converted Charlotte mourns the loss of Christmas. An on-the-job quickie with Samantha gets Smith fired from a catering gig.

Carrie begins to feel attached to Aleksandr but cannot ignore his womanizing past. Together again, Steve moves into Miranda's apartment and finds it hard to avoid her angry ex-boyfriend Robert. Charlotte tries to forget her miscarriage by volunteering. Samantha accompanies Smith to an industry party hosted by Richard Wright.

Aleksandr refuses to talk about his work or introduce Carrie to his friends. Miranda adjusts to life in Brooklyn. Charlotte decides to enter Elizabeth Taylor in a dog show. Samantha makes a sex tape with Smith after a tabloid reports that she's his "fag hag".

At a birthday party for thirty-something Miranda, Carrie and her friends vow to stop worrying about finding the "perfect" male and start having sex "like men". Carrie has several encounters with tycoon heartthrob Mr. Big. Miranda starts dating nice-guy Skipper Johnston. Charlotte goes on a date with Capote Duncan, but when she tells him she won't have sex with him, he goes to a club and winds up going home with Samantha.

After Miranda and Skipper bump into each other at the convenience store, they sleep together for the first time. Carrie interviews Barkley, a modelizer who videotapes his conquests. Derek, a male model client of Stanford Blatch, spends the night with Carrie after a fashion show, although they don't sleep together. Samantha chases Barkley while at a fashion show, in order to be taped.

Carrie and Mr. Big have their first official "date", but Carrie suspects Mr. Big is keeping her secret from his social circle. Miranda dates a man from her gym class, but she discovers a spanking video in Ted's apartment.

Charlotte is dating Jack, who wants a threesome, but she is unsure. Carrie discovers that Mr. Big has an ex-wife, and feels threatened. Samantha is seeing a married man; when his wife finds out, she proposes a threesome to keep their marriage together. Miranda feels unattractive and looks for affirmation that she isn't.

Mr. Big tells Carrie he's never going to marry again, which unsettles her. Miranda introduces the friends to the Rabbit, a mechanical aid, and Charlotte becomes addicted. Stanford Blatch proposes to Carrie as a cover, so he can inherit his part of the family fortune.

Carrie accidentally suggests that her friend Susan Sharon leave her domineering, violent husband. Miranda builds up the courage to talk dirty in bed. Charlotte tries to replace the perfect man with the perfect dog. Samantha gets dragged to couples' therapy with James and tries to avoid talking about her real problem with their sex life.

Carrie tries to get Big to stop checking out other women when they're together. Miranda and Steve's opposite schedules become a problem. Samantha runs into an old hockey-player boyfriend who is now a blonde drag queen named Samantha. Charlotte is turned-off when she dates a man who has not been circumcised; Carrie points out to Charlotte that 85% of men are not circumcised while Samantha claims to prefer uncircumcised men.

Carrie tries to leave her mark at Big's place by leaving some personal items behind. Miranda finds out that one of her ovaries has stopped producing eggs. Charlotte dates Stefan, a pastry chef who she mistakenly thought was gay but is, in his own words, a "gay straight man". Samantha tries to get revenge on Dominic, her ex who broke her heart.

Carrie tries to make a relationship with her "fuck buddy." Miranda dates an abusive, condescending lawyer. Charlotte becomes a free-wheeling dater and double-books dates with two guys on the same night. Samantha overhears the couple moaning next door, and decides to outdo them.

Carrie obsesses about her perfect relationship when Aidan suggests she meet his parents. Miranda enjoys her intimate life with Steve. Charlotte gets upset when a married friend won't set her up with his bachelor buddy. Samantha tries Viagra while sleeping with a doctor.

Carrie realizes she wants to get back together with Aidan. Miranda gets a surprise when she sleeps with "marathon man". Charlotte and Trey decide to start trying to have a baby. Samantha uses fake nipples and attracts a man who uses "baby-talk" during sex.

Carrie is dragged to Aidan's country home in Suffern, New York. Charlotte visits the MacDougal "compound" in Connecticut. Miranda yells at Steve when he tells her he has testicular cancer but has no clue about his condition. Samantha gets annoyed when her dates keep asking her what she's doing "next weekend".

Carrie realizes her relationship with New York City is as dysfunctional as is her relationship with men. Charlotte decides she needs to distance herself from her former life as "Mrs. MacDougal". Miranda tries to adjust to her new life with her baby, Brady Hobbes. Samantha gets phone calls from Richard begging her to take him back.

Carrie gets an offer from a publisher who wants to make a book out of her column. Charlotte takes a self-help seminar and takes affirmations to try to find love again. Miranda agrees to have Brady baptized, and chooses Carrie as the godmother. Samantha takes Richard back, despite the girls advising against it.

Carrie works with publicist Samantha to try to get the perfect look for her book cover. Charlotte starts reading self-help books. Miranda goes to Weight Watchers to lose her baby weight. Samantha gets upset when she feels the girls are judging her outrageous sex life.

Carrie goes to San Francisco to promote her book and visit Big. Charlotte sleeps with her unappealing (to her) divorce lawyer, Harry Goldenblatt. Samantha accompanies Carrie to California, looking for a good time.

Carrie is invited to go up to their Hamptons beach house by Patience and Peter, but in the morning she bumps into Peter in the hall without his underwear on. Some friends introduce her to Sean, 'The Marrying Guy'; when she can't keep up on his quick-march to commitment, he ditches her for commitment-phile Charlotte. Miranda's colleague from work, Jeff, introduces her to a lesbian, Sid, at a baseball game, and they are invited to her senior partner's dinner party.