An anecdote about Elizabeth (Sarah Wynter) typifies how problematic it is for successful New York women to find a good man. Next, 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 (Jeffrey Nordling), but when she tells him she won't ha
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. The "Derek" character is supposedly based on one-time Calvin Klein underwear model Michael Bergin, with whom Cand
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, she recommends 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 as a couple.
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 (Timothy Olyphant) for a fling, which turns out not to be so glamorous in the light of day. Charlotte despairs over the possibility of having anal sex. Samantha dates a younger chef, but finds the appeal wearing off.
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 vulva for his latest exhibition. Samantha tries to get a reservation at a hot new restaurant.
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 named Ted, but she discovers a spanking video in his 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 dates a man who prefers oral sex while Miranda becomes jealous after seeing Skipper with another woman. Notes: First guest star appearance of Justin Theroux.
Carrie finds out that Big was married once, and that he had a threesome. Charlotte's boyfriend wants to have a threesome. Miranda feels left out because she's never been "threesome material", so she responds to a classified ad to validate her sexual appeal. Samantha becomes involved with a married man, and his wife offers to have a threesome to keep the marriage together, which Samantha declines.
Carrie is unhappy when Mr. Big tells her that he never wants to get married again. Stanford Blatch proposes to her in order to please his grandmother and inherit his part of the family fortune. Samantha's latest pet project is "The Turtle", one of New York's most successful yet style-impaired bachelors. Charlotte becomes addicted to a rabbit vibrator called "The Rabbit".
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.
Carrie's relationship with Mr. Big has been going on for long enough that it is becoming less physical, especially after she farts in bed. Charlotte is dating a man who isn't interested in sex anymore thanks to the side-effects of Prozac. Samantha discovers that not having sex can be erotic. Miranda realizes that she hasn't had sex for months.
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.