The women attend the New York City Fire Department’s Calendar Contest in Staten Island. There, Samantha meets her dream hunk but their time together is cut short. Carrie meets Bill Kelley, a politician, who tries to make the move on her. Charlotte declares that she’ll get married before the end of the year, then goes on a date with Arthur. Miranda refuses to have help after having laser surgery.

After three weeks, Carrie and Bill Kelley take their relationship to the next level but ends after he reveals his fantasy. Charlotte moves forward with her goal to get married by the end of the year. Samantha meets a bachelor who isn’t her perfect match height wise but a match between the sheets. Miranda confronts Steve about becoming exclusive.

Carrie's Sunday brunch is ruined by seeing Mr. Big and Natasha's wedding announcement in the newspaper. Later, Carrie runs into Natasha while shopping, making her bad day even worse. Samantha takes the girls to a day at the spa where Charlotte is too self-conscious to bare all in the steam room. Meanwhile, Miranda's new cleaning lady takes her job too far when she tries to clean up Miranda's life.

When Carrie finds out that Sean, her new boyfriend, likes both men and women, she tries to not let it bother her, but has a hard time succeeding. Charlotte meets a photographer, Baird Johnson, who asks to take her picture. Samantha is forced to fire Matt, her assistant, but later sleeps with him, and Miranda invites Steve to move in with her.

Charlotte thinks it's going well with her new boyfriend, Brad, until she discovers he's a bad kisser. In order to impress Aiden, Carrie tries to quit smoking cold turkey. Samantha goes on a date with an African-American until she finds out his sister isn't as open-minded as she is. Miranda learns she has to be more supportive in her relationship with Steve.

Carrie wonders why Aiden won't sleep with her even after a romantic bath together. But Carrie finally realizes that she's gotten used to skipping romance and having sex right away. Alexander Lindley, Charlotte's new boyfriend, talks too much while in bed, upsetting Charlotte. Miranda contracts an STD and has to let her previous boyfriends know that they might have an STD as well. Meanwhile, Samantha is forced to move when she's blamed for letting in a man who robs a resident at gunpoint.

Carrie is invited to meet Aiden’s parents but can’t deal with the pressure and tells him no. But after she sees Mr. Big and Natasha together, she changes her mind. Charlotte meets Trey MacDougal, a single doctor, and they hit it off right away. Samantha starts to date Mark, a doctor who takes viagra despite not needing it, which leads Samantha to take some as well. Meanwhile, Miranda continues to adjust to her life with Steve.

After dating Trey for a while, Charlotte begins to think he's the one. Carrie runs into Mr. Big, who leaves her confused when he tells her he can't stop thinking about her. Samantha worries that she's hit menopause and Miranda hits her end with Steve and breaks up with him.

Even after breaking up, Steve sleeps on Miranda’s couch during his apartment hunt and Miranda becomes hurt when he finds someone new. Charlotte finally meets her one goal in life, even though it wasn’t how she planned it. Mr. Big tells Carrie that his relationship with Natasha isn’t going well, leading them to share a passionate night together. Meanwhile, Samantha has problems with Adam.

When Aiden tells Carrie he loves her, Carrie feels more and more guilty about her night with Mr. Big. Charlotte becomes upset when Trey asks for a prenup before their wedding. Meanwhile, Miranda discovers the ups and downs of phone sex and Samantha comes down with the flu and feels that she’ll end up alone when she has no one to take care of her.

Carrie continues her affair with Mr. Big but is put into a rough situation when Natasha catches her leaving Big's. Carrie turns to Miranda for advice and she tells her to end the affair. Meanwhile, Charlotte picks out the perfect wedding dress and Samantha's boyfriend makes her take an AIDS test before sleeping with her.

Carrie continues to debate whether or not to tell Aiden about her fling with Big. The girls go out with Charlotte the night before her wedding but Charlotte starts to have doubts about marrying Trey. Meanwhile, Miranda pretends she's a stewardess to meet men.

Carrie, Samantha, and Miranda head to Los Angeles so Carrie can talk to companies about making her column into a movie, where she meets with Matthew McConaughey, a Hollywood actor/producer. However, things at the meeting don't go well and Carrie leaves. Samantha meets a dildo model who invites the girls to a party. Meanwhile, Charlotte and Trey have a sexless honeymoon, leaving Charlotte to wonder what the root of Trey's problem really is.

During their second week in Los Angeles, Carrie spends the night with Keith Travers, a man that lets Carrie and Samantha into a movie screening. Miranda meets up with Lou, an old friend from New York, but finds out he's changed since he moved to New York. After still not having sex with Trey, Charlotte flies to L.A. to be with the other girls.

Samantha is hired as a publicist for a 13 year-old’s Bat Mitzvah and learns that the 13 year-old girls are as oversexed as Samantha. Charlotte forces Trey to see a sex therapist. Carrie meets a man at a comic book store and soon falls in love with his apartment but doesn’t feel the same way about his mother. Miranda has to wear braces but has them removed when a date thinks he’ll get stuck in them.

When Miranda’s date fails to show up, she calls him but finds out that he died the night before. At the wake, Miranda hits it off with one of Carrie’s ex-boyfriends despite Carrie warning her about him. Carrie speaks at a seminar about meeting men but the cynical audience ask her pointed questions and begin see that she’s not suited to teach the seminar. Samantha befriends Claire Ann, who she thinks is her equal until Claire Ann takes flirting with a man too far.

Charlotte, who continues to feel frustrated about not having sex with Trey, starts a fling with the McDougal's gardener but is caught, leading to Trey and Charlotte to become separated. Carrie gets mugged after being snubbed by Natasha at a restaurant. Samantha makes Carrie go with her to a party, which turns out to be a dorm party. Miranda dates the detective investigating Carrie's mugging.

Mr. Big invites Carrie to lunch, and she accepts. When she tells Miranda about the lunch, the two end up having their first fight ever. Samantha can’t sleep because of noisy prostitutes, but ends up inviting them to a party with the girls. Trey finally comes to Charlotte, ready to overcome his problem, and Miranda runs into Steve.