Season 2

June 20, 1999

Carrie turns freakish herself after dating a string of freaky guys and freaks out the very normal Ben when trying to discover his secret freakiness. Miranda dates "Manhattan Guy," a guy who hasn't left Manhattan in ten years. Charlotte dates the renowned "Mr. Pussy" and tries to make a real relationship out of it. Samantha decides to get plastic surgery and freaks out during the consult.

June 27, 1999

Single and fabulous Carrie gets a horrible photo taken for the cover story of New York Magazine: Single and Fabulous...?. Miranda fakes orgasms with her current boyfriend. Charlotte starts dating her handyman. Samantha dates a club owner, who calls them a "we" right away.

July 4, 1999

Carrie starts seeing Mr. Big again. Miranda buys her own apartment on the Upper West Side. Charlotte meets a recent widower at a cemetery. Samantha's actions with a married man gets her in trouble with the New York high-society "ladies who lunch" and only a titanic star can help her out.

July 11, 1999

Carrie starts to "officially" date Mr. Big again. Miranda dates a guy who insists on watching porn while they have sex. Fed up with cheating men, Charlotte spends time with her new friends, the "Power Lesbians." Samantha starts dating her gym instructor who "brands" her with a lightning bolt.

July 18, 1999

Carrie gets fed up with Big's inability to pay attention to her. Miranda inadvertently sets her interior designer up with a long-distance would-be boyfriend, and they marry after only four weeks. Charlotte has a "warp speed" relationship with a guy she meets at the wedding. Samantha is upset when she experiences "déjà-screw": sleeping with a guy she previously did fifteen years ago.

July 25, 1999

A frustrated Carrie tries to get Big to make time to meet the girls. Miranda meets Steve Brady, a cute bartender who wants to be more than a one-night stand. Samantha dates an incredibly wealthy man in his seventies with a sumptuous lifestyle and a pocket full of Viagra.

August 1, 1999

Carrie tries to get Big to stop checking out other women when they're together. Miranda and Steve's opposite schedules become a problem. Samantha runs into an old hockey-player boyfriend who is now a blonde drag queen named Samantha. Charlotte is turned-off when she dates a man who has not been circumcised; Carrie points out to Charlotte that 85% of men are not circumcised while Samantha claims to prefer uncircumcised men.

August 8, 1999

Carrie gets fed up with high society while at an Upper East Side party with Big. Miranda and Steve have an argument over money and social status. Charlotte meets Wiley Ford, the movie star and joins his entourage. Samantha dates a wealthy real-estate developer with a Southeast Asian live-in servant who has her master wrapped around her little finger.

August 15, 1999

Carrie tries to leave her mark at Big's place by leaving some personal items behind. Miranda finds out that one of her ovaries has stopped producing eggs. Charlotte dates Stefan, a pastry chef who she mistakenly thought was gay but is, in his own words, a "gay straight man". Samantha tries to get revenge on Dominic, her ex who broke her heart.

August 22, 1999

Carrie is horrified when Big casually tells her he's moving to Paris for seven months. Miranda dates a man who only wants to have sex in places where they might get caught. Charlotte meets Buster, a high-end shoe salesman with a serious foot fetish. Samantha introduces the girls to a hot new S&M restaurant.

August 29, 1999

Carrie starts going to therapy after obsessing about Big for too long. Offended by the diagnosis of dating men who are wrong for her, she dates cute fellow-patient Seth (Jon Bon Jovi)...a guy who loses interest in women after sleeping with them. Miranda plays "peek-a-boo" with her cute across-the-airshaft neighbor. Samantha dates a sports fanatic whose mood depends on who won the game that night.

September 5, 1999

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.

September 12, 1999

Carrie dates an author who has a premature ejaculation problem and finds that she regrets having to break-up... with his perfect family. Child-phobic Miranda dates a divorced father who has a son. Charlotte's brother Wesley stays with her after his wife leaves him. Samantha gives Charlotte's brother what he really needs: sex.

September 19, 1999

Carrie dates a recovering alcoholic who becomes obsessed with her. Charlotte is determined to learn how to have good sex after her latest partner falls asleep on her, and drags the girls to a Tantric sex class. Samantha gets an offer to have a threesome with two curious gay friends.

September 26, 1999

Carrie unexpectedly runs into Mr. Big—and his new 27-year-old girlfriend, Natasha—at a Hamptons party. Miranda tries in vain to have some mature fun in the Hamptons. Charlotte pretends to be in her twenties so she can date a cute 26-year-old. Samantha's 25-year-old ex-assistant is hired to throw a big Hamptons party using her Rolodex for the guest list.

October 3, 1999

After learning of Big's engagement, a freaked-out Carrie tries to cope with the ramifications. Miranda sleeps with Steve for the first time after their breakup. Charlotte tries to overcome her fear of horseback riding. Samantha dates a guy who's "Mr. Too-Big", determined to overcome his over-endowment.