"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.

"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 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; Samantha gets to know her doorman better; Charlotte dumps and eligible guy with the wrong china pattern.

"There are no available men in their thirties in New York. Giuliani had them removed along with the homeless." - Miranda Carrie discovers the limitations of going out with a twentysomething hunk. Charlotte's boyfriend has a sexual favor to ask; Samantha comes to the sobering realization that she'll always be older than her boy toy.

"Where's the line between professional girlfriend, and just plain professional?" - Carrie Carrie goes on a date with a gorgeous French architect who shows his thanks with a thousand dollars; a famous painter uses Charlotte as one of his models; Skipper becomes sexually obsessed with Miranda.

"A guy can just as easily dump you if you f*ck him on the first date as he can if you wait until the tenth." - Samantha How many of us out there are having sex with people we are ashamed to introduce to our friends? Carrie thinks Mr. Big is keeping her a secret, while Miranda discovers a secret about her new boyfriend. Samantha has never been discreet with anyone she's ever slept with, and Charlotte divulges her past love affair with one of God's chosen people.

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 out in Connecticut, and they each react differently. Carrie is “late”, and wonders how she would be as a mother. Samantha throws an “I don't have a baby” shower party.

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.