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". Carrie has several encounters with tycoon heartthrob Mr. Big. Miranda starts dating nice-guy Skipper Johnston. 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.

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. Derek, a male model client of Stanford Blatch, spends the night with Carrie after a fashion show, although they don't sleep together. Samantha chases Barkley while at a fashion show, in order to be taped.

Mr. 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 for a fling, which turns out not to be so glamorous in the light of day.

Carrie bumps into international party-girl Amalita and her latest man Carlo in a shoe store, who in turn introduce her to a French Architect, Gilles. He leaves Carrie $1,000 on the nightstand after a one-night stand. Charlotte meets Neville Morgan, a renowned artist, who paints pictures of her vagina for his latest exhibition.

Carrie and Mr. Big begin dating on a regular basis, but she learns after bumping into him that he is dating other women. Samantha begins to look for an apartment to purchase.

After being introduced as "a friend" to his mother, Carrie realizes her relationship with Mr. Big is one-sided and breaks up with him. Miranda dates an up-and-coming playwright who is also an up-tight Catholic. Samantha falls in love with a perfect man, but he doesn't measure up to her requirements. Charlotte gets psychic readings to see if she'll ever marry.

Carrie tries to make a relationship with her "fuck buddy." Miranda dates an abusive, condescending lawyer. Charlotte becomes a free-wheeling dater and double-books dates with two guys on the same night. Samantha overhears the couple moaning next door, and decides to outdo them.