Original air date: 06/06/1999 Runtime: 25:19 min. In the Season Two premiere, Carrie follows up the struggle of breaking up with Mr. Big by dating a 'new Yankee.' Meanwhile, Samantha expresses dissatisfaction with her boyfriend's lack of manhood and Charlotte's man has a problem with his crotch adjustments.
Original air date: 06/20/1999 Runtime: 25:57 min. Carrie dates numerous freaks before turning into one herself when she meets a nice guy named Ben. Meanwhile, Samantha goes on a date with a man who likes to be disciplined and Charlotte begins to realize that Mr. Pussy might be only good for one thing.
Original air date: 07/04/1999 Runtime: 27:37 min. Charlotte falls for a widower...whom she meets at a fashion designer's funeral. Meanwhile, Carrie mends some fences with Mr. Big, Samantha makes the mistake of trying to seduce a celebutante's husband, and Miranda has panic attacks after buying her own place.
Original air date: 08/15/1999 Runtime: 26:59 min. Carrie tries (unsuccessfully) to leave some feminine items behind at Big's place. Meanwhile, Miranda discovers that she has a 'lazy' ovary, Charlotte has questions about her new boyfriend, and Samantha plots a revenge scheme against an ex.
Original air date: 08/22/1999 Runtime: 29:04 min. Big tells Carrie that he is moving to Paris for six months, Samantha introduces the girls to the hottest S&M restaurant in town, Charlotte's shoe fetish is counterbalanced, and Miranda meets a guy who only enjoys sex when he is at risk of being caught.