The 5 Episodes of Sex and the City That Hold Up the Best—And 5 That Don’t

Every Sunday for six seasons, Sex and the City followed along as Carrie (Sarah Jessica Parker), Charlotte (Kristin Davis), Miranda (Cynthia Nixon), and Samantha (Kim Cattrall) entertained fans with stories from the dating trenches. To modern eyes, the show, which launched in 1998, is a time capsule. It is filled with artifacts of a much different era: answering machines, (eventually) giant cell phones, Harvey Weinstein references, near-constant cigarette smoking, physical instead of cloud backups for computers, and freelance writer salaries that are sufficient to afford a New York City apartment. There are plenty of elements to the show that transcend the decades, though, particularly issues surrounding love, friendship, and especially the love for your friends. However, there are many other elements in Sex and the City that don’t quite land more than 20 years since the show ended, including plot lines that are no longer acceptable and jokes that are certainly not funny.

For her part, Parker is aware that the show hasn’t aged entirely well. When asked about it at the Wall Street Journal’s Future of Everything Festival in 2018, Parker noted that at the time, “There were no women of color, and there was no substantial conversation about the LGBTQ community” on the show or seemingly behind the scenes.

Parker also admitted that the “enormous amount” of change in New York City’s political, social, and economic climate would impact the series if it were made today. “I think it would be a different show, honestly,” she said. She added that her character was reflective of the time and era in which she was written. “Carrie Bradshaw is very much a product of her generation and I think her conversations about sexual politics and intimacy spoke to the years,” she said. “I think that she would have a lot to say about [the #metoo movement], and I would be curious to read [her] column if she could sit back and look at it.”

The showrunners also seem aware of some of their past mistakes, and tried to address them in the Sex and the City reboot, And Just Like That, which has more diversity and more LGBTQ+ representation. 

As Season 3 of And Just Like That kicks off, take a look back at some of the episodes that have fared well over the years and some where the content and language are of a bygone era—and probably best left there.

5 SATC episodes that stand the test of time

“A Woman’s Right to Shoes” (Season 6 Episode 9)

This episode finds Carrie single once again, and feeling complicated about it when she attends a baby shower for her friend, Kyra (Tatum O’Neal). Carrie is not happy when Kyra asks her to remove her shoes before coming into the apartment, because, as she notes, her Manolo Blahniks make the outfit. When her shoes are stolen, Kyra offers to pay to replace them, but she balks when she discovers the $485 price tag. She thinks the shoes are unnecessarily extravagant and refuses to subsidize Carrie’s lifestyle. However, in a message that has resonated with single people for years, Carrie points out to Kyra that, actually, she’s the one who has been subsidizing her lifestyle—as well as those of her other married friends—by forking over cash for bridal showers, bachelorette parties, destination weddings, and baby showers. Since Carrie hasn’t had a wedding or a baby, she’s just paying to support her friends’ life choices without any reciprocity. So when Carrie calls up Kyra to inform her that she’s getting married—to herself!—and announces that she is “registered at Manolo Blahnik,” it’s a battle cry for all the single ladies.

Read more: Sex and the City Is Nothing Without Samantha Jones

“Ex and the City” (Season 2, Episode 18)

Sex and the City is at its best when it offers its viewers a meditation on the good, bad, and ugly of relationships, including all the heartbreak. Here, after projectile vomiting when she runs into Big and his new girlfriend Natasha in the Hamptons during the last episode, Carrie decides to try and be friends with Big. Over a boozy lunch, Big breaks the news that he is now engaged. In this episode, Carrie has to grapple with her feelings about Big really and truly moving on and the result is a painful and realistic look at a topic that will resonate as long as people have exes. 

Plus, this episode also highlights SATC’s other strength—the enduring power of female friendship. Here, the fab four wind up at a bar near the Plaza where Big and Natasha are hosting their engagement party. As Carrie understandably pouts, “Why her??” They realize it all comes down to life lessons learned from the film, The Way We Were, with Carrie slowly coming to terms with the past and the future. 

“Coulda, Woulda, Shoulda” (Season 4, Episode 11)

There aren’t too many TV shows that offer women a choice when their characters wind up pregnant. In this episode, SATC uses its archetypal characters to showcase reproductive options and the realities of it all that women face. Here, Miranda discovers that she accidentally got pregnant with Steve’s (David Eigenberg) baby and doesn’t want to have it, while Charlotte, desperate to have a baby, learns she has just a 15 percent chance of conceiving a baby with her husband, Trey (Kyle MacLachlan). Over an awkward brunch, Miranda tells an already-upset Charlotte the news, and when she reveals that she doesn’t want to have the baby, Charlotte can’t handle it and leaves. Later, in one of the series’ most poignant moments, Miranda runs into a devastated Charlotte on the street and even though she declines company, Miranda follows her home, a few paces behind, to make sure she’s okay. The two friends may be on separate paths, but eventually figure out how to support each other and their decisions, even when they disagree. The supportive and (mostly) nonjudgmental nature of the friends’ advice is reminiscent of the time that, even as she is about to walk down the aisle, Carrie reminds Charlotte that she doesn’t have to go through with her wedding. 

This is also the episode where Samantha covets a Birkin and ends up alienating Lucy Liu in the process, which is an equally memorable, if less emotional, plot point.

“My Motherboard, My Self” (Season 4, Episode 8)

When Miranda’s mother dies unexpectedly the friends grapple with grief and death, some more capably than others. The parallel storyline is that when Carrie’s computer crashes, she learns a valuable lesson about relying on others. As a longtime strong and independent woman, this is particularly challenging because she and Aidan recently exchanged house keys and she is working through her need for independence and his team-oriented need to problem solve. The result is an emotional episode about what support in relationships (and bras) looks like and why sometimes it is hard to accept. It all comes to a powerful and heartrending funeral scene where the friends are all there for Miranda and then Aidan, and Miranda’s ex Steve, quietly show up to support them in turn. It is those little moments, whether asked for or not, which is what true support looks like. It’s one of the show’s strongest reflections on the idea of chosen families and how friends can show up for you in unexpected ways.

“Ring A Ding Ding” (Season 4, Episode 16)

Carrie struggles with one of the more pragmatic elements of adulting—paying the rent. She is forced to accept the reality of her financial situation when she and Aidan split and he wants her to buy him out of the apartment or vacate the premises. The result is Carrie having to come face-to-face with her finances, including a brutal moment when Miranda does the math and Carrie realizes, “I spent $40,000 on shoes and have nowhere to live??” Carrie can’t get a loan due to her finances (she has less than $2000 in her checking and savings combined), so she decides to go to Big for financial advice and he offers her a loan, which she rightly declines. However, when Miranda and Samantha offer to help and Charlotte doesn’t, Carrie turns into the worst version of herself, taking out her financial frustrations on her friend. The episode is a gimlet-eyed look at the realities of adulthood, the difficult sides of adult friendship and adult finances, and figuring out a path forward with a little help from your friends. For what it’s worth, some budgeting experts estimate that it would actually take Carrie 172 years to realistically afford her apartment, but hey, who is counting? 

“No Ifs, Ands, or Butts” (Season 3, Episode 5)

In this episode, perhaps surprisingly directed by Nicole Holofcener, Samantha starts a short-lived relationship with an “African-American” record executive named Chivon, played by Asio Highsmith. This episode highlights Sex and the City’s lack of diversity, giving Black characters important supporting roles for the first time but in a plot filled with racist tropes, clichés, stereotypes, and insulting lines. Like when Samantha can’t help telling her friends, “I don’t see color, I see conquests,” to which Carrie replies, “Talk about affirmative action!” Samantha seems to have genuine chemistry with Chivon, but his sister Adeena (Sundra Oakley) is not thrilled about the relationship and confronts Samantha about it. When Samantha asks why it’s such a big deal, because race shouldn’t matter— implying that she is actually the victim of racism—Adeena brushes it off and tells her it’s “a black thing.” The two women end up in a fist fight in the club and Samantha breaks up with Chivon for refusing to stand up for her. The episode is clunky, offensive, and very outdated. 

Oakley told Vanity Fair in 2018 that while she was thrilled to get a role on such a popular show, “even a few years later … it’s like, oh man, why did it have to be that way? Why couldn’t it have been a different story?”

“Models and Mortals” Season 1, Episode 2

It’s hard to imagine that even in 1998 it was alright for someone to record a person in a sexually explicit situation without their consent and yet it happens in just the second episode of the series. In this episode, Carrie’s supposed friend Barkley is revealed to be a modelizer, as in he prefers dating models to mere mortals, because he considers models to be “easier”. He also refers to models as “things,” but “beautiful things”, erasing their personality and individuality entirely. If that wasn’t vile enough, he then reveals his collection of tapes filled with intimate moments captured on film. When Carrie asks if the models know they are being taped, he replies, “Maybe.” Barkley seems to consider these tapes, all made without consent, an extension of his “artistic work” and Carrie barely blinks at the revelation, seeming to shrug it off as more quirky than criminal. Samantha, however, finds Barkley’s hobby intriguing and even asks him to film her. While he “only tapes models” she explains that she doesn’t mind, making her possibly the only woman he records with her consent.

“Boy, Girl, Boy, Girl” Season 3, Episode 4

Carrie has started dating a new man, Sean (Eddie Cahill), and while things seem to be going well, she is caught off guard when he shares that he is bisexual and enjoys the company of men and women. Carrie, a journalist who writes about sex and dating for a living, tells the girls over brunch that she doesn’t think bisexuality is real, but rather a “layover on the way to gay town.” Charlotte adds that she believes people should “pick a side and stay there,” while Miranda decides that bisexuality is both “greedy” and “a problem.” Notably, in an earlier season, Miranda brought a woman to a dinner party to impress a colleague whose wife wanted “to add a lesbian couple” to their inner circle, which could also be considered greedy and problematic. Carrie ultimately breaks up with Sean after a spin-the-bottle party with a “pupu plater of sexual orientation”, calling herself “an old fart” because she couldn’t understand being attracted across genders. Despite what Carrie stated, a 2023 Gallup poll found that 4.4% of U.S. adults and 57.3% of LGBTQ+ adults reported that they are bisexual.

“Cock A Doodle Do” Season 3, Episode 18

When Samantha moves to New York’s at-the-time rapidly gentrifying Meatpacking District, she finds herself in a nightly yelling match with the sex workers who have been in the neighborhood far longer than she has. The sex workers are described in a voiceover by Carrie as “pre-op transexual hookers” who were “half-man, half-woman, and totally annoying”. When Samantha complains to her friends about wanting her new, expensive, trendy neighborhood to be quieter in the evenings, her friends let loose with a cavalcade of denigrating and dated “jokes” that, to modern ears, feel both hurtful and cringeworthy. When hollering out her window fails to stop the nightly street party, Samantha decides to take noise control matters into her own. She not only continues hollering, using a derogatory slur for transgender people, she then throws a bucket of water on them to convince them to move further away. When the sex workers egg her apartment, it’s hard not to cheer them on and then be completely confused when they all show up after Samantha invites them to a rooftop BBQ.