The ladies take full advantage of an opportunity to judge contestants for a fire department calendar competition, with Carrie landing the attentions of an attractive politician.
As Miranda puts her commitment to Steve to the stress test, Carrie tries adjusting to life as paramour to a politician.
Charlotte's high at the prospect of getting married is dampened by the intrusion of unpleasant financial matters; laid low by the flu, Samantha worries that she'll grow old alone; as Aidan unveils his deepest feelings for Carrie, she tries hard to rise above her baser urges.
While Samantha prepares to take a spa day, Carrie finds herself annoyed by Big's current girlfriend. Elsewhere, Miranda struggles with her housekeeper's well-meaning intrusiveness.
While Miranda frets that she's too masculine and Charlotte surprisingly takes to the gender-bending image she dons for an artist, Carrie struggles to be open minded about the fact that her new man likes boys as well as girls.
As Miranda struggles to be supportive of Steve, Carrie struggles to kick her smoking habit, especially when she meets a great-looking, non-smoking furniture designer. Meanwhile, Charlotte dates a bad kisser and Samantha encounters unexpected difficulties in dating a Black man with an overprotective older sister.
Aidan's slow and steady courtship makes Carrie realize she's gotten into the habit of skipping romance in favor of quick sex. Meanwhile, Charlotte frets that her latest lover can only achieve satisfaction if he hollers obscenities at the height of the act and Samantha's neighbors express displeasure that one of her late-night rendezvous led to a stick-up of one of the residents.
Samantha tries a sex enhancement drug; also, Charlotte's delighted to meet a doctor while Carrie feels mysteriously uneasy about her relationship with Aidan.
As good as things are going with Aidan, Carrie's rattled when Big tries to contact her. Meanwhile, Charlotte becomes convinced that Trey is the one for her and Miranda stunned to hear Steve wants the two of them to have a baby.
As Samantha dates a man who leaves a bad taste in her mouth and Miranda tries her best to cope with temporarily co-habiting with Steve even though they've broken up, Charlotte's desire to get married proves to have an unexpectedly successful outcome. Meanwhile, despite how well things are going with Aidan, Carrie finds herself relapsing into bad habits with Big.
As Charlotte determinedly prepares for her wedding, Samantha's frustrated because her latest refuses to sleep with her until she passes an AIDS test. Meanwhile, as her affair gets less and less glamorous, Carrie's guilt starts affecting her relationship with Aidan.
Wanting to drum up a date for the wedding, Miranda tries on different persona while Charlotte learns an important secret about Trey and has a falling out with Samantha, who finds herself attracted to the groom's incomprehensible Scottish cousin. Also, in the face of Aidan's strong belief in honesty, Carrie finds that deceiving him about Big is starting to really weigh on her.
While Miranda and Samantha accompany Carrie on a trip to Los Angeles to suss out Hollywood's - and specifically Matthew McConaughey's - interest in her column, back in New York, Charlotte continues, unsuccessfully, to try to tempt Trey in the bedroom.
Fed up with Trey, Charlotte joins her friends in Los Angeles, where Carrie makes a love connection with an agent, Charlotte gets reacquainted with a former New Yorker buddy who has surrendered to the charms of Southern California and Samantha wangles an audience with her idol, Hugh Hefner, and a subsequent visit to the Playboy Mansion.
While Charlotte works harder to amp things up in the bedroom with Trey, Samantha accepts a lucrative, maddening job to plan a bat mitzvah and learns age is indeed more than just a number. Elsewhere, Carrie hangs out with a rich, fun-loving guy who has trouble acting his age.
As Carrie nervously prepares for and teaches an adult education class on how to meet men, Miranda meets a new guy at the funeral for her recently deceased date. Meanwhile, Samantha and Charlotte get fed up with each other's attitude about sex.
While Charlotte finds herself captivated by a hunky gardener and Miranda's insecurity with her date's handsomeness takes an unexpected turn, Samantha grows to regret relieving a virgin of his chastity and, following a mugging that involves the loss of her beloved Manolo Blahniks, Carrie ponders the nature of karma when she learns Big and Natasha are breaking up.
Having left Trey, Charlotte resolves to forget about men altogether. Elsewhere, Miranda worries what her takeout Chinese food ordering says about the status of her love life and Samantha struggles to deal with her noisy neighbors. Also, after she and Miranda have a sobering encounter with their respective exes, Carrie wonders whether she can get closure with Big.