06/06/1999      Take Me Out To The Ballgame (24' 38")

Chris Noth (Mr. Big)

After Carrie ends her relationship with Mr. Big, she dates a new member of the Yankees team, but they bump into Mr. Big and she realises she is not over him. Miranda becomes annoyed with the others talking about nothing but men. Samantha is unsatisfied with her boyfriend's shortcomings. Charlotte has a problem with her new boyfriend, Paul Ericson, continually adjusting himself, and her attempt to improve things misfires.

13/06/1999      The Awful Truth (24' 33")

Chris Noth (Mr. Big) Willie Garson (Stanford Blatch)

Carrie reluctantly invites Mr. Big to her birthday party after he sends her flowers. Samantha tries to tell her boyfriend about his shortcomings, and he gets them to go to a therapist. Charlotte gets a puppy, Henry, in lieu of a perfect man. Miranda talks dirty with her lover, the “spring-roll man”.

20/06/1999      The Freak Show (25' 14")

Chris Noth (Mr. Big)

Carrie ruins a new relationship with Ben, a guy she meets in the park. Samantha dates Harrison, but finds he is into something she isn't. Charlotte dates Mitchell Sailor, “Mr. Pussy”. Miranda quits dating after Carrie sets her up with a blind date she doesn't like. Carrie realises she's a freak, too.

27/06/1999      They Shoot Single People, Don't They? (25' 26")

Willie Garson (Stanford Blatch)

Carrie thinks she enjoys being single, until she's late for a photo shoot and gets a bad picture on a magazine cover. Samantha dates William, a club owner, who lies about their possible future together. Charlotte tries to hook Tom, an actor friend after he decides to move to Salt Lake City. Miranda fakes ecstasy for Josh, a previous boyfriend whom she meets again.  This episode's title is a play on words with the title of the movie "They Shoot Horses, Don't They?"

04/07/1999      Four Women And A Funeral (26' 50")

Chris Noth (Mr. Big)

After one of Carrie's friend dies from heroine abuse, she reflects on how time goes by really fast and calls Mr. Big, bringing back to life a relationship that took six months to die. At first they just go out for dinner, but after not picking up his calls Mr. Big shows up and they go bowling – and later end up sleeping together. Meanwhile, Charlotte meets an attractive widower at the funeral and thinks he might be Mr. Right, after all he's been very in touch with his emotions and being a widower proofs he can commit. Everything is good – Charlotte is ok even with the fact of forever living on the shadows of his dead wife – until she finds out she wasn't the only one who resuscitated him. Miranda has a panic attack after buying her own place and having to admit to everyone that "it's just her". And Samantha experiences social hell after a high profile society woman catches Sam making out with her husband. The only one who can save her from total exclusion is Leonardo DiCaprio, who she met while helping build Carrie's dead designer house for people with substance abuse.  Samantha is a social outcast. In the original showing, she is returned to social acceptance by meeting John Kennedy Jr. After his death, she now meets Leonardo DiCaprio.

11/07/1999      The Cheating Curve (24' 20")

Chris Noth (Mr. Big)

Where does the line between cheating and not cheating stands? The four glamorous women from Manhattan discuss the topic while going through their own experiences. Charlotte is having an opening at her gallery, where she walks in on her date making out with another woman. She is intrigued by the "powerful lesbians", a group of well-dressed, successful lesbians with good shoes. She accepts an invitation of dinner from one of them and has a great time on a men-free environment (the G-Spot, the newest, hottest girls club in the city), but soon faces restrictions due to her heterosexuality. Meanwhile, Samantha discovers that her hot personal instructor (that shaved her privates in the shape of a lightening) is giving lightening to other woman. Miranda has a tough time competing with porn when she discovers her date can only have sex while watching porn. And Carrie has trouble revealing to her friends that she is back together – officially – with Mr. Big.

18/07/1999      The Chicken Dance (24' 26")

Chris Noth (Mr. Big)

Miranda is shocked when her decorator and a friend who was just staying over for a few days announce their engagement with only knowing each other for a few days. At the engagement party, Samantha nags a date for herself, and Miranda wonders if her apartment will bring good luck to everyone but her. At the wedding, Charlotte is serving as one of the bride's maid, and gets the sexiest dress she can get to walk down the isle. Her escort is a very handsome man, and within a few hours they click as if they had gone out on several dates. Unfortunately the man takes his father's side when Charlotte complains that the old man felt her up. Samantha is shocked to realize that she had already slept with her engagement party date. Miranda is stuck with the guest book and thinks she's invisible to all men. Carrie is asked to write and proclaim a poem for the bride and groom, and is hurt when Mr. Big walks out of the room to answer his phone during her reading. She is saddened with the fact that while some people can get married after 4 weeks she can't even get Mr. Big to sign a card with her.

25/07/1999      The Man, The Myth, The Viagra (24' 21")

Chris Noth (Mr. Big) David Eigenberg (Steve Brady)

Carrie continues her relationship with Mr. Big, but wants him to get to know her friends better. Samantha starts spending time with a wealthy seventy-something. Miranda has a bad experience with a married man, and starts seeing a bartender, Steve Brady.  The first appearance of Steve Brady.

01/08/1999      Old Dogs, New Dicks (26' 08")

Chris Noth (Mr. Big) David Eigenberg (Steve Brady)

Carrie tries to get Mr. Big out of some of his annoying habits. Samantha chances on an old boyfriend who is now a drag queen, named in her honor, at drag bingo. Charlotte is horrified to find she's dating an uncircumcised man. Miranda is still dating Steve, the bartender, but they have problems with incompatible life-styles and schedules.

08/08/1999      The Caste System (26' 52")

Chris Noth (Mr. Big) David Eigenberg (Steve)

Carrie decides to say "I love you" to Mr. Big, but his response isn't exactly what she was hoping for. Instead, all she got was an ugly purse. They attend a fancy party from an upstate socialite, who won't allow indoors smoking or have any brown food or drinks at the party. While out in the terrace for a smoke, Carrie runs into Jeremiah, an artist/bartender with whom she's been flirting with for a several years. While he was showing her his tattoo, Serena the socialite walks in on them, and tells Mr. Big Carrie was giving him a blowjob. Offended, Carrie leaves the party with Jeremiah, get drunk and wakes up the next morning with him on his bed. Luckily they didn't do anything, because Mr. Big called her first thing in the morning saying he does love her, but he was just afraid to say it. Meanwhile, Charlotte meets a famous actor and acts like a groupie around him. But despite making exceptions on several dating rules, she feels like she has to establish some boundaries when the guy goes too far with his sexual requests. Miranda is seeing a guy who's poorer than her, and money issues eventually lead to a breakup. Samantha is sexing a guy with a servant, but she feels like there's no space for her between their employee-employer relationship after repeatedly being thrown out of bed by the two-faced jealous maid.

15/08/1999      Evolution (26' 13")

Chris Noth (Mr. Big) Willie Garson (Stanford Blatch)

Carrie thinks her relationship with Big has evolved enough to the place where she can leave stuff at his place. She purposely leaves a few items on his bathroom, only to be surprised by Big the next morning with a bag with all her items in it. Carrie is confused and tries to discuss it with him, but realizes she doesn't have to leave her marks on his place to know they're in a relationship. Meanwhile, Miranda feels her biological clock ticking when her gynecologist tells her one of her ovaries has stopped production. She starts taking hormones and going out on dates with guys she'd never go – like her co-worker with the hair plugs – but a discussion about freezing eggs leads her to realize she's only 33 and still has one ovary working. Samantha has the chance of getting back to the one guy who broke her heart, but can't resist the temptation of jumping to bed with him. Her vengeance plan goes down the drain when he dumps her and she realizes she hasn't evolved past having feelings quite yet. And Charlotte finds a piece of the male evolution of her own: a man who could be either a gay straight or a straight gay. The difference? The gay straight is nothing but the product of overexposure to the high life in Manhattan, but is still straight. Confused, she decides to go forward with the guy, but realizes her male side isn't as evolved as Stephan's female side.

22/08/1999      La Douleur Exquise! (28' 13")

Chris Noth (Mr. Big) Willie Garson (Stanford Blatch)

Carrie freaks out when Big breaks the news to her that he might have to move to Paris for a year. She is revolted that all this time she thought of them as a "we" while his conception of "we" was "me and my penis". Angry and drunk after several shots of Cosmopolitan, Carrie calls Big at 5:30 am discussing their relationship. The next morning she drops by with greasy food and suggests that she too should move to Paris so they can stay together. Big shoots her idea down and says that if she moves to Paris it has to be because of her and not him. Carrie is even more revolted, but ultimately accepts that the man of her life has to go. Meanwhile, Charlotte's fetish with shoes brings her to a shoe salesman with a feet fetish who gives a 500-dollar pair of shows for free. She can't keep it and try to return, but the guy won't take it. Instead, he convinces her to model 6 new shoes that just came to the store. And Miranda meets a guy on a bookstore who likes to have sex where he can get caught. The only problem is his fetish is not about him, but her getting caught (which she does, in his bedroom, by his parents, when they walk in on them having sex and he still doesn't stop). Stanford faces his own fetishes when he meets a guy online and goes to an underwear-only gay bar.

29/08/1999      Games People Play (20' 31")

Willie Garson (Stanford Blatch)

Carrie meets a new man, Seth Robinson, in her analyst's waiting room. Samantha dates a sports fan whose sex life is in sync with his teams' successes. Charlotte joins a bridge club to try to meet someone. Miranda flirts with a Peeping Tom in the apartment opposite.  The crew can be seen reflected on the TV in the back when Carrie writes her article

05/09/1999      The Fuck Buddy (24' 20")

Ben Weber (Skipper Johnston)

Getting over Mr. Big, Carrie makes a date with a special friend, and tries to make it a fuller relationship. Samantha has an interesting time with the couple next door until reality strikes. After Charlotte summons the courage to ask men for dates, she gets carried away and starts to double book. Miranda dates a man who she thinks is highly-strung, but is really just unpleasant.  This is Ben Webber's last episode. He played Miranda's ex, Skipper Johnson.

12/09/1999      Shortcomings (26' 04")

Carrie dates a writer, Vaughn, and meets his very open family, but finds them all too much. Samantha dates Charlotte's brother, Wesley, who is in town following his separation. Miranda dates a divorced father, and finds that his family ties are stronger than his feelings for her.

19/09/1999      Was It Good For You? (26' 35")

Carrie meets a man and they go out for coffee. She gives him her phone number and when he doesn't call she wonders what she might of done to turn him off. She later runs into him in the street and he tells her the reason he didn't call is because he's an alcoholic and his AA sponsor told him that he shouldn't start any new relationships for at least a year. He throws caution to the wind and embarks on a relationship with Carrie. Soon enough though he becomes addicted to her instead of alcohol so she has to cut him off, which leads him to alcohol addiction once again.  Charlotte thinks she's bad in bed when a guy falls asleep while making love to her so she enrolls herself in a tantric sex workshop and signs Carrie, Samantha and Miranda up as well. They go to the workshop and they all learn how to please their partner without actually having sex and Miranda accidently gets hit by flying ejaculate.  Samantha agrees to have sex with a gay couple she knows but when the couple can't go through with it she thinks there's something wrong with her.

26/09/1999      Twenty-Something Girls Vs. Thirty-Something Women (24' 50")

Chris Noth (Mr. Big) Bridget Moynahan (Natasha)

Carrie, Samantha, Charlotte and Miranda head to the Hamptons and Charlotte meets a 26-year old guy. She tells him she's 27 and she starts to act like a girl in her twenties. They sleep together and he gives her crabs.  Samantha fires her 25-year old assistant Nina and she steals her business rolodex. She gets jealous when Nina plans "The Hamptons Hoe-Down" and people who have never shown up for her parties show up for Nina's. She decides to congratulate her and is happy to discover that Nina needs her help because nothing is going as planned and to pay her back she sets her up with Greg, the guy who gave Charlotte crabs.  Carrie gains a protege and can't believe that at 25 she's still a virgin. She goes to a book party and meets a doctor. Later at the hoe-down she runs into Mr. Big, who's back from Paris, with his twenty-something girlfriend whom he met in Paris.

03/10/1999      Ex And The City (31' 19")

Chris Noth (Mr. Big) Bridget Moynahan (Natasha) David Eigenberg (Steve Brady)

Carrie wonders why she has never become friend with an ex-boyfriend, and decides that if she must start with someone, that someone mind as well be Mr. Big. She calls him up for inviting him over for a dinner, where he breaks the news that he's proposed to his new girlfriend, Natasha. Shocked, Carrie storms out of the restaurant, shouting and yelling about how with her he had a commitment problem for 2 years, but had found no difficulties on proposing to whats-her-name after 5 months. Meanwhile, the other gals try to find friends themselves. After running away (literally) from Steve, Miranda receives a visit from him in her place and ends up in bed with him – they're friends who have sex. Charlotte tries to become friends with a horse and overcome her trauma caused by her best friend – a horse – who threw her from his back when she was a child. And Samantha faces a challenge: she meets a man with a huge penis. So big that she isn't sure she can make it. When the doubt becomes a certain, she proposes they stay just friends – for the safety of her own vagina!