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Samantha becomes involved with a married man, and his wife offers to have a threesome to keep the marriage together, which Samantha declines. Big tells her that he never wants to get married again.
Stanford Blatch proposes to her in order to please his grandmother and inherit his part of the family fortune.
Samantha's latest pet project is "The Turtle", one of New York's most successful yet style-impaired bachelors.
Charlotte becomes addicted to a rabbit vibrator called "The Rabbit".
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.
The "Derek" character is supposedly based on one-time Calvin Klein underwear model Michael Bergin, with whom Candice Bushnell was once briefly involved.
Bergin has stated he auditioned for the job of his alter-ego, but was told he was too old for the part.
Carrie is invited to go up to their Hamptons beach house by Patience and Peter, but in the morning she bumps into Peter in the hall without his underwear on.
Some friends introduce her to Sean, 'The Marrying Guy'; when she can't keep up on his quick-march to commitment, he ditches her for commitment-phile Charlotte.
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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".