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 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.

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.

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.

After being introduced as "a friend" to his mother, Carrie realizes her relationship with Mr. Big is one-sided and breaks up with him. Miranda dates an up-and-coming playwright who is also an up-tight Catholic. Samantha falls in love with a perfect man, but he doesn't measure up to her requirements. Charlotte gets psychic readings to see if she'll ever marry.

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.

Single and fabulous Carrie gets a horrible photo taken for the cover story of New York Magazine: Single and Fabulous...?. Miranda fakes orgasms with her current boyfriend. Charlotte starts dating her handyman. Samantha dates a club owner, who calls them a "we" right away.

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 is horrified when Big casually tells her he's moving to Paris for seven months. Miranda dates a man who only wants to have sex in places where they might get caught. Charlotte meets Buster, a high-end shoe salesman with a serious foot fetish. Samantha introduces the girls to a hot new S&M restaurant.

Carrie starts going to therapy after obsessing about Big for too long. Offended by the diagnosis of dating men who are wrong for her, she dates cute fellow-patient Seth (Jon Bon Jovi)...a guy who loses interest in women after sleeping with them. Miranda plays "peek-a-boo" with her cute across-the-airshaft neighbor. Samantha dates a sports fanatic whose mood depends on who won the game that night.

Carrie continues dating her politician beau, but finds his sexual fetish to be anything but 'golden'. Miranda doesn't know how to respond when Steve asks her to "go steady". Charlotte throws a "used date" party to find a new man. Samantha dates a short man who shops at the Boy's Department in Bloomingdale's.

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's smoking becomes a problem when she goes on her first date with Aidan Shaw. Miranda makes more time for Steve in her life. Charlotte dates the worst kisser she's ever met. Samantha dates a black man whose sister is racist.

Carrie struggles to find the right time to tell Aidan about her affair. Miranda tells a guy she's a stewardess in hopes of getting a date. Charlotte has her dream wedding and marries Trey MacDougal—even after attempted late-night tryst reveals Trey's serious shortcomings. Cunning linguist Samantha sleeps with Trey's Scottish cousin, despite being unable to understand him.

Carrie is reluctant when asked to be a celebrity model in a high-profile fashion show. Miranda gets a lesson in confidence when a buff guy at the gym asks her out. Charlotte works up the courage to look at her "depressed" vagina in a hand-mirror. Samantha immortalizes herself by having nude photographs taken.

Carrie finds time away from stay-at-home boy Aidan with a gay Aussie shoe distributor at the exclusive Bungalow 8. Charlotte and Trey separate permanently after their apartment is photographed in House & Garden. Miranda accidentally outs her co-worker after he tells the office gossip that she's pregnant. Samantha tells Richard she loves him while high on ecstasy.

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 invites Jack Berger to her book opening party, which turns out to be a huge event. Charlotte butts heads with Bunny MacDougal. Miranda's single life and her life with Brady conflict. Samantha gets an impulse-buy chemical peel that goes awry.

Carrie deals with her past with Aidan when she runs into Nina Katz, who had dated Aidan after he and Carrie split up. Charlotte gets a tough lawyer to go up against Bunny in a fight to keep her apartment. Miranda has no one to turn to when she needs help taking care of Brady. Samantha tries to return a spent vibrator, then spends some of her free time on Miranda.

Carrie receives a big royalty check for her book sales, which upsets Berger— whose book deal has been dropped. A lovesick Miranda helps Steve bake cupcakes—for his new girlfriend. Charlotte is reluctant to date after Harry leaves her. Samantha takes charge of the PR for Jerry's struggling play where he gives a striking—and nude—performance.

Carrie finds that a casual fling with Harry's best man is a pain in the neck. Miranda is scared of meeting Steve's new girlfriend. After Harry accidentally sees Charlotte in her wedding dress before the big day, she is convinced their wedding is cursed. Self-sufficient Samantha struggles without a man around.

Carrie's shoes are stolen at a party; the hostess (Tatum O'Neal) not only refuses to apologize, but shames her for her extravagant footwear — and lifestyle choices. Miranda gets chicken pox, and she flirts with the handsome black doctor who just moved into her building. Charlotte must adjust to living with Harry (and his tea bags) in her pristine apartment. Children misbehaving in nice restaurants annoy Samantha.

Carrie's high-school sweetheart visits her in New York—on his way to a mental asylum in Connecticut. Miranda develops a crush on her attractive neighbor Robert, the team doctor for the Knicks. In order to get into an exclusive pool at the SoHo House, Samantha pretends to be a member — and British. Geri Halliwell and David Duchovny guest-star.

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".

Petrovsky hosts a dinner party for Carrie's inner circle, and makes a shocking announcement. Later, the death of an old party friend (Kristen Johnston) helps Carrie reach a big decision.