A laid back Sunday brunch is ruined when Carrie sees Big and Natasha's wedding announcement in the New York Times. Twenty five, tall, beautiful, and married, Natasha brings out Carrie's worst insecurities. When Carrie bumps into Natasha in the dressing room of a clothing boutique, Carrie wonders: Are there women in New York City who live for the sole purpose of making other women feel bad about themselves? To relieve some stress, Samantha takes the girls out for a day at the spa. Charlotte however, can't seem to let go of her body image issues and get naked in the steam room. Samantha gets a tip that Kevin, one of the massage therapists, performs sexual favors, but when he doesn't deliver, Samantha makes her own move and grabs his crotch. The spa bans Samantha, but she gets Kevin fired. Charlotte returns to the spa and nervously bares it all; she's validated when another woman compliments her breasts. Meanwhile, Miranda's new Ukranian housekeeper takes cleaning up Miranda's life too far -- with lectures about marriage and herbal teas. When she replaces the vibrator in Miranda's "goodie drawer" with a statue of the Virgin Mary, Miranda puts her in her place. Carrie tries to impress Natasha by looking fabulous at a high society luncheon. But it's all for naught because Natasha doesn't show up. After trying too hard and buying clothes she couldn't really afford, Carrie feels like a loser -- until she gets Natasha's thank you note featuring an embarrassing spelling error.

Charlotte's first date with Brad is going spectacularly, until it comes time for the "kiss" at the doorway which is more like a series of sloppy licks from a Great Dane. Charlotte tries to give some emergency kissing lessons, but he's just beyond repair. Carrie is also pursuing a new prospect -- Aidan the furniture designer. To impress him, Carrie buys one of his leather chairs. Aidan is bedazzled with Carrie, until she takes out a cigarette and he lays down the law: he just can't date a smoker. Carrie tries to go cold turkey, but Aidan catches her sneaking a cigarette after their date. Determined to give the relationship a shot, Carrie says goodbye Marlboro, hello Nicoderm. Stanford scores Marty, a nice guy who turns out to have a an extensive doll collection, which is fine until Stanford breaks a doll during sex. Samantha also has a new man -- Chivon, a sexy African-American. Things are steaming along until Chivon's sister interferes and tells Samantha she's got the wrong color skin for her brother. Samantha fights for her right to date anyone and everyone, but Chivon ultimately gives in to his sister's demands. Meanwhile, Steve wins the chance to win one million dollars if he scores a basket from center court. Steve asks Miranda to watch him practice a few shots on the basketball court, but she's too busy which infuriates him. Finally, Miranda learns she needs to be more supportive.