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At a birthday party for thirty-something Miranda, Carrie and her friends vow to stop worrying about finding the "perfect" male and start having sex "like men". Charlotte goes on a date with Capote Duncan, but when she tells him she won't have sex with him, he goes to a club and winds up going home with Samantha.
Samantha chases Barkley while at a fashion show, in order to be taped.
Aside from the four main characters, Big (played by Chris Noth) is the only character to appear in both the pilot show and the series finale "An American Girl in Paris, Part Deux". After Miranda and Skipper bump into each other at the convenience store, they sleep together for the first time.
Carrie interviews Barkley, a modelizer who videotapes his conquests.
Charlotte meets Neville Morgan, a renowned artist, who paints pictures of her vagina for his latest exhibition. Big have their first official "date", but Carrie suspects Mr. Miranda dates a man from her gym class, but she discovers a spanking video in Ted's apartment.
Miranda's colleague from work, Jeff, introduces her to a lesbian, Sid, at a baseball game, and they are invited to her senior partner's dinner party. Big and Carrie continue to bump into each other during social events, which leads them to try to organize their first "drink thing".
On a night out, Carrie meets twenty-something Sam (Timothy Olyphant) for a fling, which turns out not to be so glamorous in the light of day.