At a birthday party for thirtysomething Miranda, Carrie, and Samantha decide from now on, they'll have sex like men. Carrie has sex with an old flame, who's fine with being a sex object, then later runs into Mr. Big, both as she leaves the apartment and at Chaos. Miranda is set up with Skipper, who she hates at first but begins to warm up to. Charlotte decides not to sleep with Capote Duncan, who then asks her for cab fair so he can go get laid. Samantha, in turn, meets Capote at Chaos and has a one night stand with him.
"Suddenly, I felt like I was wearing patchouli in a room full of Chanel". - Carrie
Miranda makes the mistake of going out with a "modelizer" (someone who's obsessed with models); Samantha chooses to go out with a modelizer and has her sexual encounter videotaped; Carrie experiments with Derek the Model and flirts with Mr. Big.
Carrie gets invited to a house warming party by a married couple. She brings Charlotte and Samantha to the party to meet new guys, but all the male guests are married. Meanwhile, Miranda is set up with a woman and decides to let her co-workers believe she's a lesbian in order to help her career.
Carrie and Samantha both date men in their twenties but both break it off after they realize they're too old to date twenty-something guys. Charlotte gets advice from Carrie, Samantha, and Miranda about whether or not to have anal sex with her boyfriend.
Charlotte is invited to go to Connecticut with Neville Morgan, a famous artist. Carrie goes on a date with a French architect who helps her with her financial problems. Skipper tells Carrie that he's become obsessed with Miranda.
Carrie goes on her first date with Mr. Big but worries she hurt their relationship by sleeping with him, leading her to research peoples' secret relationships. Meanwhile, Miranda uncovers her boyfriend's secret.
Carrie is spending all her time with Mr. Big, and then finds he's not being exclusive, which she can't handle. Miranda has broken up with Skipper, but when she sees him out with another woman, she tries to get back together, on a non-exclusive basis, which he can't handle. Samantha goes apartment hunting, supposedly with a realtor on an exclusive basis, but actually continues to use others.
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.
The four friends are invited to a baby shower for Laney, a former wild child turned soccer mom, who gets them thinking about their own futures. Carrie is 'late' and is forced to think about being a mother while Charlotte worries she may never have a child. Meanwhile, Samantha throws an "I don't have a baby" shower.
Carrie's relationship with Mr. Big is moving into a more mundane, less physical stage, and she's worried whether it's due to her inadvertant flatulent indiscretion. Charlotte is dating a former lover of Carrie's, and finds that he's not interested in sex anymore. Samantha discovers that not having sex can be erotic. Miranda hasn't had sex for months.
Miranda's lover always showers afterwards, as he's a Catholic. Carrie discovers Mr. Big takes his mother to church on Sundays. Samantha falls in love with a perfect man, but he doesn't measure up to her requirements. Charlotte consults a series of soothsayers about whether she will ever get married. Carrie breaks up with Mr. Big.