Carrie and Mr. Big keep bumping into each-other till they date (without that term) at Samantha's hot restaurant PR-opening, but he cancels last minute. The cook, just Jon, is reserved for Samantha's bed, but his hot friend Sam, also twenty-something (those always seem to know the right people) flirts with Carrie; Big turns up saying he was on time but couldn't find her, time to leave town. At a twenties club Sam takes Carrie on his lap and kisses really well, five hours long, and again while she helps him pick a shirt. Samantha eagerly reports on a night of sex with Jon, twenties-men are so hot and consider thirties-women a good deal. Charlotte is embarrassed Bryant explicitly asked for anal sex, Miranda warns her not to give in on respect which is power, Samantha says a hole is just that; Charlotte gets a decent first date. Samantha realizes she'll always feel older with twenties-men, and resolves to give them up. After Big brought his just divorced friend Jack to their drink, Carrie seeks consolation in Sam's bed, in heaven when spooned, only to wake up in his nightmare apartment which comes with a room mate, but no toilet paper, and runs off to her ultimate addiction- the shoe store.

As Carrie's birthday approaches, she finds herself at the center of a friend's domestic drama, while Samantha faces the truth, Miranda has an awakening, and Charlotte seeks solace in a new male.