After learning of Big's engagement, a freaked-out Carrie tries to cope with the ramifications. Miranda sleeps with Steve for the first time after their breakup. Charlotte tries to overcome her fear of horseback riding. Samantha dates a guy who's "Mr. Too-Big", determined to overcome his over-endowment.

Carrie meets a politician at a FDNY calendar benefit in Staten Island. Miranda gets help from Steve after she undergoes LASIK eye surgery. Tired of waiting for a fairytale romance, Charlotte begins aggressively searching for a "Prince Charming" to marry. Samantha dates the pinup-boy fireman she met at the benefit.

Carrie continues dating her politician beau, but finds his sexual fetish to be anything but 'golden'. Miranda doesn't know how to respond when Steve asks her to "go steady". Charlotte throws a "used date" party to find a new man. Samantha dates a short man who shops at the Boy's Department in Bloomingdale's.

Carrie thinks about men and the future when no one shows up for her birthday party. Miranda confronts her married friends about her single life. Charlotte tries to deal with her separation from Trey. Samantha tries to seduce a celibate monk. The girls make a pact that they are soulmates, and men are nice guys to have fun with.

Carrie is reluctant when asked to be a celebrity model in a high-profile fashion show. Miranda gets a lesson in confidence when a buff guy at the gym asks her out. Charlotte works up the courage to look at her "depressed" vagina in a hand-mirror. Samantha immortalizes herself by having nude photographs taken.

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 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.

While nervously anticipating her first date with Berger, Carrie runs into Aidan for the first time since their breakup, and is surprised by how far he's moved on. Miranda realizes she's in love with Steve—only to hear he has a new girlfriend. Charlotte struggles with Harry's assertion that he can only marry a Jew. Samantha sleeps with a stockbroker who gives insider tips while inside her.

Carrie and Berger's dates sizzle in the restaurants, but fizzle in the bedroom. Miranda becomes addicted to a British show featuring an interracial romance. A tenacious Charlotte pursues converting to Judaism for Harry. Samantha and the girls go to a cold-food restaurant where Samantha meets hot waiter Jerry Jerrod (Smith).

Carrie begins to feel attached to Aleksandr but cannot ignore his womanizing past. Together again, Steve moves into Miranda's apartment and finds it hard to avoid her angry ex-boyfriend Robert. Charlotte tries to forget her miscarriage by volunteering. Samantha accompanies Smith to an industry party hosted by Richard Wright.