Samantha is hired as the publicist for Jenny Bryer's A-list Bat Mitzvah. Jenny and her galpals are so New York, and so over-sexed that Samantha starts to wonder whether there's any difference between Jenny at 13 and Samantha at 34. Miranda's new braces also have her feeling like a teenager these days. After a new date fears he'll get caught in her jaws, she dumps the braces. Charlotte scours the internet in a desperate search for a solution to Trey's sexual problem. When she suggests they discuss options, Trey gets angry and asks Charlotte to accept that he's just not that sexual of a guy. Finding this unacceptable, Charlotte demands they see a sex therapist whose first suggestion is they name their private parts, Rebecca and Schooner respectively. Meanwhile, Carrie meets her latest man, Wade, at a comic store. She falls in love with his amazing Manhattan apartment, until Wade's mom comes home. Carrie plays along with her mama's boy, accepting fresh-baked cookies and all, until Wade's mom busts Carrie and Wade for smoking pot. But Carrie isn't the only one busted. Charlotte wakes up in the middle of the night to find Trey masturbating in the bathroom to Juggs magazine.

Increasingly depressed by Trey's lack of libido, Charlotte finds some relief when she stumbles into the studly sweaty gardener at the McDougal country house. Carrie's guilty conscience takes a beating when she's rudely snubbed by Natasha in a restaurant. To top things off, Carrie gets mugged, losing her favorite pair of Manolo Blahniks. Carrie wonders if it isn't all karma. Detective Stevens handles Carrie's case but when Miranda shows up at the police station, the good-looking detective focuses all his attentions on Miranda. Meanwhile, Samantha tells Carrie that Natasha has left Big, causing Carrie to feel even more guilty and more determined to apologize to Natasha for wrecking their marriage. Samantha drags Carrie to a party given by a certain "Sam Jones" -- only to find out it's a dorm party and this "Sam Jones" is a college-aged virgin lad. Sam Jones falls hard for the more experienced Samantha and before Samantha knows it, she has made Sam a real man. Unfortunately, the enamored Sam becomes completely obsessed with Samantha, ultimately causing her to change her phone number. Back in the suburbs, on Charlotte's second encounter with the gardener, the two share a secret kiss, unaware that Charlotte's sister-in-law witnessed the embrace. Later that evening, the sister-in-law spills the beans to the whole McDougal clan. Trey says it's acceptable for the two of them to lead separate lives while being married. Outraged, Charlotte says they should separate for a while and Trey responds, "Alrighty." Miranda, nervous that she isn't good-looking enough for her detective date, gets drunker and drunker as the night goes on. She seduces the detective back in her apartment, but when she wakes up the next morning, she finds a note recommending she call her local AA. Carrie finally tracks down Natasha in a restaurant and expresses how deeply sorry she is about what she did. Natasha tells Carrie that not only has she ruined her marriage, she's now ruined her lunch. Charlotte returns to the city and to her old apartment as a single woman.