"It's like the riddle of the Sphinx... Why are there so many great unmarried women, and no great unmarried men?" - Carrie At a birthday party for thirtysomething Miranda, Carrie and her friends vow to stop worrying about findng the perfect male and start having sex like men. Carrie experiments with an old flame and meets Mr. Big; Miranda warms up to Skipper; Samantha has a one night stand with a man Charlotte wouldn't sleep with on the first date.

Miranda makes the mistake of going out with a 'modelizer' (someone who is obsessed with models); Samantha chooses to go out with a modelizer and has her sexual encounter videotaped; and Carrie experiments with Derek-the-model and flirts with Mr. Big.

Carrie is invited to a couple's house in the Hamptons only to be flashed by the husband, Miranda's law firm thinks she's a lesbian and Samantha gets to know her doorman better. Meanwhile, Charlotte dumps an eligible guy with the wrong china pattern.

Carrie discovers the limitations of going out with a twenty-something hunk, Charlotte's boyfriend has a sexual favor to ask, and Samantha comes to the sobering realization that she'll always be older than her boy toy.

Carrie goes on a date with a gorgeous French architect, who shows his 'thanks' with a thousand dollars. Meanwhile, a famous painter uses Charlotte as one of his models and Skipper becomes sexually obsessed with Miranda.

Carrie thinks Mr. Big is keeping her a 'secret' while Miranda discovers a sex secret about her new boyfriend. Samantha has never been discreet with anyone she's ever slept with, and Charlotte divulges her past secret love affair with a Hasidic Jew.