To celebrate the latest advance of her book, Carrie takes Berger on a date to Prada. Berger initially feels like a fish out of water in the upscale retailer, but a few comped glasses of champagne help him to relax. Unfortunately, no amount of alcohol can help him deal with the sticker shock brought on by the price of a shirt that Carrie wants him to buy. After leaving Prada, Carrie tells Berger about her advance over a lunch date. She then gives him the Prada shirt as a celebratory gift, making him feel very uncomfortable. Later, a chance encounter with Courtney, Carrie's editor, reveals two important bits of information: that Courtney has been fired due to "low sales in her sector" and that Berger's option has been dropped by the publisher. Carrie begins to feel guilty, afraid that she's been rubbing her success in Berger's face, and that buying the expensive shirt may have been a bad idea.
Samantha continues her burgeoning relationship with Jerry, even going so far as to travel to Brooklyn to see him in a play. The show ("Full Moon") bores her into numbness until Jerry steps onstage and drops trou. After the show has ended and the pair are in Samantha's bedroom, she decides that she's going to help him to become the "next big thing" in New York. She works her magic to add buzz to the show, but not before officially changing his name from Jerry Jerrod to Smith Jerrod.
Sadly, Miranda and Charlotte aren't doing as well as Samantha in the relationship department. Charlotte is still smarting from being dumped by Harry, while Miranda's feelings for Steve continue to grow. Charlotte goes to Anthony for dating advice, but even he can't brighten her spirits. While trying to earn "points" with Steve, Miranda accidentally agrees to bake cupcakes for his girlfriend Debbie. Luckily, Miranda's self-respect wins out, and the cupcakes remain unfinished.
Thanks to Samantha, the official opening of Full Moon becomes the hottest event in the city. Carrie invites Berger, but he shocks her by picking her up for the premiere on his motorcycle. Carrie risks getting a bad case of helmet hair, and winds up petrified by the speed at which Berger drives across the Brooklyn Bridge. When they finally stop, an argument ensues. After much soul-baring, things seem to resolve themselves... but when it comes time to enter the theatre, Berger begs off and leaves Carrie holding the fabulous bag. The play is a huge success (largely due to Smith), but Carrie's future with Berger is in question.