New York City columnist Carrie Bradshaw and her friends vow to stop worrying about finding the perfect mate - and start "playing the field" like men. Their new stance soon leads to Carrie meeting Mr Big, Miranda warming to Skipper, and Samantha having a one-night stand.
Miranda makes the mistake of going out with a "modelizer" (someone who is obsessed with models), whilst Samantha chooses to go out with a modelizer and has their erotic encounter videotaped. Meanwhile, 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. Elsewhere, Miranda's law firm think she's homosexual, Samantha gets to know her doorman better, and Charlotte dumps a suitable guy because of the pattern on his china set.
Carrie discovers the limitations of going out with a twenty-something hunk, Charlotte's boyfriend has a sexual favour 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", whilst Miranda discovers a secret about her new boyfriend. Meanwhile, it comes to light that Samantha has never been discreet with anyone she's ever slept with, and Charlotte divulges a secret love affair from her past.
Carrie wants a monogamous relationship with Mr Big, while Samantha refuses to have one with her realtor. Meanwhile, Miranda's feelings for Skipper intensify, and Charlotte is faced with her new boyfriend's intimate demands.
Carrie discovers not only that Mr Big was married before, but that he and his ex participated in an explicit encounter. Meanwhile, Charlotte's boyfriend wants to add another woman to their relationship, and Samantha becomes a little too involved with a married couple.
Mr Big tells Carrie he will never marry again, whilst Samantha suffers a harsh dumping - sending her back into the arms of "The Turtle" (an investor with bad breath). Meanwhile, Miranda introduces Charlotte to "The Rabbit", which turns Charlotte into a recluse.
A baby shower for Laney - a wild-child-turned-soccer-mom - gets the girls thinking about their futures. Meanwhile, Charlotte is fearful she may never have the daughter for which she has been preparing her whole life, and Carrie is late for her period.
An accidental emission has Carrie certain that she and Mr Big will never share a bed again - whilst the last three months have Miranda convinced she will never share a bed with a man ever again. Meanwhile, tantric celibacy leaves Samantha craving old-fashioned intimacy.
In the season finale, Mr Big introduces Carrie to his mother as his friend, causing Carrie to ponder where their relationship is headed. Meanwhile, Charlotte discovers that all the fortune-tellers in the city agree on one thing - her eternal status as a single woman.