The girls attend the Hamptons wedding of an over-the-hill socialite and a lounge singer whom they all thought was gay. Carrie encounters Jack Berger again. Charlotte goes public with her relationship with Harry. Miranda gets more comfortable with the baby and with her role as a mother. Samantha throws a huge party at Richard Wright's Hamptons house.

Carrie desperately tries to get everyone together for Charlotte's "thirty-faux" birthday. Charlotte doesn't want to turn 36 because she feels she's getting old. Miranda goes to Atlantic City with the girls, feeling self-conscious about her weight. Samantha is paranoid that Richard is cheating with the entire female hotel staff.

Carrie deals with her past with Aidan when she runs into Nina Katz, who had dated Aidan after he and Carrie split up. Charlotte gets a tough lawyer to go up against Bunny in a fight to keep her apartment. Miranda has no one to turn to when she needs help taking care of Brady. Samantha tries to return a spent vibrator, then spends some of her free time on Miranda.

Carrie invites Jack Berger to her book opening party, which turns out to be a huge event. Charlotte butts heads with Bunny MacDougal. Miranda's single life and her life with Brady conflict. Samantha gets an impulse-buy chemical peel that goes awry.

Carrie realizes her relationship with New York City is as dysfunctional as is her relationship with men. Charlotte decides she needs to distance herself from her former life as "Mrs. MacDougal". Miranda tries to adjust to her new life with her baby, Brady Hobbes. Samantha gets phone calls from Richard begging her to take him back.

Carrie gets an offer from a publisher who wants to make a book out of her column. Charlotte takes a self-help seminar and takes affirmations to try to find love again. Miranda agrees to have Brady baptized, and chooses Carrie as the godmother. Samantha takes Richard back, despite the girls advising against it.

Carrie works with publicist Samantha to try to get the perfect look for her book cover. Charlotte starts reading self-help books. Miranda goes to Weight Watchers to lose her baby weight. Samantha gets upset when she feels the girls are judging her outrageous sex life.

Carrie goes to San Francisco to promote her book and visit Big. Charlotte sleeps with her unappealing (to her) divorce lawyer, Harry Goldenblatt. Samantha accompanies Carrie to California, looking for a good time.