We are introduced to Carrie Bradshaw, who writes a sex column for the New York Post. She uses her personal sex life and that of her friends as research for her column. Her three closest friends: Samantha, a Public Relations Executive who owns her own firm, Miranda, who is a well established lawyer at a great law firm and Charlotte who works at a prestigious art gallery.
Carrie's column this week is about women who have sex like men. At a restaurant with her gay friend Stanford, she runs into Kurt, an old boyfriend, who treated her like garbage, and decides to use him as her test subject. She goes back to his place and he performs oral sex, but she leaves when it's time to do him. She feels powerful and energetic after leaving him high and dry. Her purse is knocked out of her hand by a passerby, and a very handsome, dark haired man helps her pick up the contents. Later in the evening Samantha points out the mystery man to Carrie and tells her he's as: "You see that guy, his the next Donald Trump only he's younger and much better looking". With that line, the very mysterious name Mr. Big is born. Carrie neglects to tell Samantha that she has already had an encounter with him, probably because Samantha wants to hit on him herself, but he shoots her down with each come on line.
Carrie's friend Skipper, who is a hopeless romantic, tells her that it's been a year since he has had sex, and if she could fix him up with any of her friends. Although Carrie knows that Miranda will hate Skipper because he is so nice, she still sets them up on a date. Later in the evening the two meet at Chaos and although Miranda seems annoyed with Skipper, she kisses him.
After leaving Chaos in the wee hours of the morning, Carrie is unable to get a cab, and just when she ponders walking home, Mr. Big pulls up in his chauffeured car, and offers her a ride. He asks what she does for a living and he is very interested when she answers. He tells her that he doesn't have sex like a man minus the feeling, and when she asks him if he has ever been in love, he answers very simply: "Abso-fucking-lutely".
Charlotte is on a great first date, with a very successful and well known bachelor by the name of Capote Duncan. After dinner, the two return to his place but, when he wants to become intimate, Charlotte turns him down, which he respects. He stops a cab for her, then he hops in beside her and asks the driver to drop him off at Club Chaos. When Charlotte has a shocked and bewildered look on her face, he gives it to her straight, "I get where you're coming from, but I really need to have sex tonight". So much for playing by the rules.