Sex and the City: Season 2
1999 · 18 episodes · ★ 6.3
What Season 2 of Sex and the City
Season two opens with Carrie freshly split from Mr. Big. She soon starts dating a Yankees player, though she realizes things aren't over between her and her ex. Miranda gets tired of her friends only talking about men, Samantha won't settle for her partner, and Charlotte deals with Paul Ericson, a boyfriend who causes her trouble. The leads face insecurities, breakups and emotional expectations as they move forward at work and in their personal lives. Charlotte adopts a puppy to fill the void left by a perfect man, and Samantha suggests her boyfriend go to therapy for his sexual problems. Each of them makes her own choices in a city full of dates.
Season 2 Episodes
2x01 Take Me Out to the Ballgame
Carrie meets "the new Yankee," Joe, at a baseball game, all the while preparing for her first post-breakup encounter with Big. Miranda gets fed up with the girls always talking about men. Samantha gets frustrated with James' "deficiencies". Charlotte dates a guy named Paul Ericson who has a tendency to adjust his package... a lot.
Directing: Allen Coulter · Writing: Michael Patrick King · Starring: Robert T. Bogue, Mark Devine, Larry Dolby Jr., Marilyn Dobrin
2x02 The Awful Truth
Carrie accidentally suggests that her friend Susan Sharon leave her domineering, violent husband. Miranda builds up the courage to talk dirty in bed. Charlotte tries to replace the perfect man with the perfect dog. Samantha gets dragged to couples' therapy with James and tries to avoid talking about her real problem with their sex life.
Directing: Allen Coulter · Writing: Darren Star · Starring: Daniel Gerroll, James Goodwin, Molly Price, Robin Irwin
2x03 The Freak Show
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.
Directing: Allen Coulter · Writing: Jenny Bicks · Starring: Ian Kahn, Marc Kudisch, Claudia Besso, Jamie Denbo
2x04 They Shoot Single People, Don't They?
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.
Directing: John David Coles · Writing: Michael Patrick King · Starring: Mark Feuerstein, Tom Gilroy, Robert Montano, Hope Adams
2x05 Four Women and a Funeral
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.
Directing: Allen Coulter · Writing: Darren Star, Jenny Bicks · Starring: Kurt Deutsch, Seth Barrish, Porter Beerman, Lisa Butler
2x06 The Cheating Curve
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.
Directing: John David Coles · Writing: Darren Star · Starring: Rob Campbell, Mary B. McCann, Tamara Tunie, Juliana Francis
2x07 The Chicken Dance
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.
Directing: Victoria Hochberg · Writing: Cindy Chupack · Starring: Carrie Preston, Stephen Barker Turner, David Beach, Buzz Bovshow
2x08 The Man, the Myth, the Viagra
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.
Directing: Victoria Hochberg · Writing: Michael Patrick King · Starring: Bruce MacVittie, Spiro Malas, Bill McHugh, Dina Paisner
2x09 Old Dogs, New Dicks
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.
Directing: Alan Taylor · Writing: Jenny Bicks · Starring: Alex Draper, Jackie Beat, Peter Bucossi, Norman Douglass
2x10 The Caste System
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.
Directing: Allison Anders · Writing: Darren Star · Starring: Sam Ball, Brian Van Holt, Harry Bouvy, Pamela Gray
2x11 Evolution
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.
Directing: Pam Thomas · Writing: Cindy Chupack · Starring: John Shea, Dan Futterman, Philippe Brenninkmeyer, Elaine Bromka
2x12 La Douleur Exquise!
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.
Directing: Allison Anders · Writing: Michael Patrick King, Ollie Levy · Starring: Will Arnett, James Urbaniak, Matt Beisner, Matt Conley
2x13 Games People Play
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.
Directing: Michael Spiller · Writing: Jenny Bicks · Starring: Jon Bon Jovi, John Dossett, Anne Lange, Steve Albert
2x14 The Fuck Buddy
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.
Directing: Alan Taylor · Writing: Darren Star, Merrill Markoe · Starring: Dean Winters, Ben Weber, Louis Aguirre, Divina Cook
2x15 Shortcomings
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.
Directing: Daniel Algrant · Writing: Darren Star, Terri Minsky · Starring: Justin Theroux, David McCallum, Daniel McDonald, Valerie Harper
2x16 Was It Good for You?
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.
Directing: Daniel Algrant · Writing: Michael Patrick King · Starring: Richard Joseph Paul, Elżbieta Czyżewska, Kevin J. Flynn, Seán Martin Hingston
2x17 Twenty-Something Girls vs. Thirty-Something Women
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.
Directing: Darren Star · Writing: Darren Star · Starring: Patrick Breen, Rachel Miner, Anson Mount, Jamie Forehand
2x18 Ex and the City Season Finale
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.
Directing: Michael Patrick King · Writing: Michael Patrick King · Starring: John Enos III, LaChanze, Peter Davies, Michael H. Ingram
Season 2 Cast
Kim CattrallSamantha Jones18 episodes
David EigenbergSteve Brady4 episodes
James GoodwinJames2 episodes
Robert T. BoguePaul EricsonEpisode 1
Mark DevineYankee JoeEpisode 1
Maggie KileyWoman #1Episode 1
Keira NaughtonYuppie WomanEpisode 1
Frank AnelloYankee Frank (uncredited)Episode 1
Neal JonesRichardEpisode 1
James Augustus LeeManEpisode 1
Neil PepeAaronEpisode 1
Amy PovichWoman #1Episode 1All Seasons
Season 11998 · 12 ep. · ★ 5.7
Season 32000 · 18 ep. · ★ 6.2
Season 42001 · 18 ep. · ★ 6.2
Season 52002 · 8 ep. · ★ 6.3
Season 62003 · 20 ep. · ★ 6.0Where to Watch Season 2 of Sex and the City
Frequently Asked Questions
How many episodes are in Season 2 of Sex and the City?
Season 2 of Sex and the City has 18 episodes.
When did Season 2 of Sex and the City premiere?
Released June 6, 1999.
Where to watch Season 2 of Sex and the City?
Available by subscription on Amazon Prime Video, Movistar Plus+ Ficción Total, HBO Max, Amazon Prime Video with Ads, and HBO Max Amazon Channel (availability may vary by country).
What is the best episode of Season 2?
According to audience reviews on TMDB, episode 2x17, "Twenty-Something Girls vs. Thirty-Something Women," with a 6.9.