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.

Mr. Big and Carrie continue to bump into each other during social events, which leads them to try to organize their first "drink thing". On a night out, Carrie meets twenty-something Sam for a fling, which turns out not to be so glamorous in the light of day.

Carrie bumps into international party-girl Amalita and her latest man Carlo in a shoe store, who in turn introduce her to a French Architect, Gilles. He leaves Carrie $1,000 on the nightstand after a one-night stand. Charlotte meets Neville Morgan, a renowned artist, who paints pictures of her vagina for his latest exhibition.

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.

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.

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 women attend a baby shower for their one-time wild-child friend Laney in her new buttoned-down Connecticut-suburb environs. Carrie is forced to think about motherhood by her late period. Miranda regards the other guests as part of the cult of The Motherhood. Still-single Charlotte fears her dreams of being a wife and mother are slipping away. Samantha throws a "no-baby shower" in response to the one the four women attended.

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.