Opinion

The Most Pivotal Sex and the City Episode From Every Season 

An argument for the seven most important—if not necessarily the best—episodes of the enduring original series.
Sex and the City The Most Pivotal Episode From Every Season
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Sex and the City has been, in no uncertain terms, covered to death. Every possible angle and opinion already exists in writing, from the smarty-pants stuff to the personal essays to the debatable hot takes. The HBO series is so analyzed that there are articles covering the best coverage of the coverage. But of course it is. The show is a deeply important one for reasons other people have written about at length (see: smarty-pants stuff, above), but it also has fought to the death to remain a topic of conversation by refusing to ever go away. 

Should the Sex and the City experience have ended in 2004 with a bedazzled pink Motorola letting us know his name is John? I think yes. The 94-episode DVD set, followed by the emergence of HBO Go and on demand, followed by syndication runs on TBS and E!, probably would have been enough to sustain both die-hard fans and newcomers, but I also understand the allure of cashing in on something with the cultural cachet that Sex and the City had and has. And so, four years after the series ended, we were hit over the head with a bouquet of flowers by a jilted bride and a somewhat depressing three-hour epilogue. Then, two years after that, we’re riding camels in Abu Dhabi. 

And now, on December 9, 2021, we have the ultimate resuscitation: a 10-episode reboot titled And Just Like That…, which will undoubtedly give the internet license to once again scrutinize the show to absolute death, especially since it appears to have undergone a tonal transformation to fit the times: Nonwhite characters are (finally) included, a queer storyline might ensue, and menopause is looming for our main characters. 

So why am I cramming my voice into the oversaturated coverage of this inescapable show? I've spent a large part of my life with Sex and the City, which aired for six seasons starting in 1998. I was a teenager who was born and raised in a rapidly gentrifying New York City when the first episode aired and have rewatched it every single year—fine, day—since. At 17, I found the series mildly amusing but ultimately the sexploits of 30-something career women couldn't have been further from what I cared about the time. 

But art is frozen and we are not, so it’s been a disorienting experience to continuously consume Sex and the City and not only catch up to the characters, agewise, but start to surpass them. With each older and wiser rewatch, I see new flaws and absurdities that didn’t register before—a sign I'm able to think critically about a show I love—and it’s a humbling and strange sensation to suddenly find yourself older than the characters you initially thought of as...old. I’ll be interested to see how they're portrayed in the reboot now that time has unfrozen and we’re seeing them in their 50s and 60s and not 30s.

But before we drop in on 2021 Carrie, Miranda, and Charlotte (and raise a Cosmo to the Samantha-shaped hole sure to be felt), I figured I’d do my small part as a person working on the internet and contribute yet another (insightful or overwritten—you decide!) word salad on the original Sex and the City series. The theme: the most pivotal episode from each season, and context into what made it so vital. 

Season 1, episode 5: “The Power of the Female Sex” (1998) 

Season-one Sex and the City was a vastly different show than what it ultimately turned out to be. The fourth-wall breaking, the gimmicky man-on-the-street contrivance, the bland but realistic fashion, and the gritty camera style started to be put out to pasture by season two, but in episode five, a phenomenon was highlighted that had just started to take shape and form the New York we know today: the contrast between people who were able to use New York as a glittering playground and those who lived and worked in the city and experienced it in a more authentic way. 

Though nothing major happened in the way of lasting character development, the episode has an element of hyperrealism—and relevancy—thanks to the introduction of Amalita Amalfi. Though she's written as parody, Carrie's European acquaintance represents a very specific type of woman that started to descend on the city as it got safer, richer, and flashier during the 1990s. “An international party girl” is what Carrie calls her, but anybody who's spent ample time in New York has met her at least once: an attractive woman of indeterminate means who hustles her way into the most exclusive parties, the best restaurants, fabulous group trips, and—facts—has an uncanny ability to hook rich men.  

As soon as Carrie meets up with Amalita and her crowd at Balzac, the same restaurant she and Samantha couldn't get into at the top of the episode (an accurate nod to the timely emergence of the city's status hotspots), Amalita shoves her wrist in Carrie's face, proffering the diamond bracelet she received that day from new boyfriend Carlo at Van Cleef & Arpels. “Twelve thousand dollars!” she barks in a tongue-rolling Italian accent, cackling hysterically.  

Carrie is struggling to make ends meet but is charming enough to parlay her way into Amalita's moneyed inner circle if she wants to. The setup isn't subtle, but it does start to cement Carrie as something of a moral, relatable heroine for the millions of “real” women watching the show. Yes, she sleeps with Gilles, the irresistible French architect Amalita introduces her to after knowing him only a few hours, but she's filled with self-recrimination when he leaves her $1,000 on the nightstand, despite her declaring that she's not in a good financial way. “We had such a fantastic connection, then he leaves me money,” Carrie later tells her friends. “I don't understand. What exactly about me screams ‘whore’?”

The next time she sees Amalita at Balzac, Carlo has been replaced by a new rich man with a friend who immediately starts leering at Carrie. She resists—not before her voice-over lets us know she understands who Amalita is, and what might happen if she gives in. “I realized that I could leverage myself like the human equivalent of a sexy junk bond,” she says. “I'd parlay that $1,000 into a trip to Venice, into a nice piece of jewelry, a rich husband, followed by a richer divorce.” She resists, and goes back to her ordinary season-one life of playing poker with her girlfriends to rack up a few bucks. 

As a stand-alone 24 minutes, it does well to highlight a very specific moment in New York and also explains where our characters stood on gender roles (“You're like a Harvard Law Lorena Bobbit,” Samantha tells Miranda during a debate about men potentially abusing their power for sex). In the context of the series, though, the episode has a certain irony given how its pecuniary realism was pretty much abandoned soon after. In the seasons that followed, Carrie's financial status was rarely referenced, which kicked off the audience's running side-eye at the magical realism that is Carrie's New York existence: being able to afford to use the city as her playground on a tabloid newspaper columnist's salary.

Season 2, episode 17: “Twenty-Something Girls vs. Thirty-Something Women” (1999)

Season two marks the arrival of Sex and the City as a thing, a burgeoning cultural phenomenon that starts to settle into its narrative footing. The fourth wall has been rebuilt, the clothes are getting more interesting, Carrie's iconic curls are long and flat. Almost every episode is a win (minus “The Caste System,” which should be wiped from syndication for obvious reasons), and a case could be made for several being integral. What’s pivotal about this episode is its heightened meditation on age but also it’s the one where viewers really start to believe Carrie has moved on from Big, who fled to Paris after they shared a seemingly meaningful connection during the middle of the season. 

Throughout the entire episode, Carrie's confidence is palpable for a change. She seems like she's getting her mojo back and—unlike Charlotte and Samantha for their own reasons—presents as if she's truly comfortable being in her 30s. When the other women gripe about the world validating the existence of twenty-somethings, Carrie is the one with the perspective. “The only thing worse than being single in your 30s is being single your 20s.”  

The point is highlighted further by the younger women featured in the episode—the 25-year-old fangirl Carrie meets in the Hamptons, Laurel, and Samantha's entitled assistant, also 25, are written as clueless half-wits, and a cocky 26-year-old dude gives Charlotte crabs. It's driven home at a book party where Carrie gets approached by a handsome doctor and banters with him like a sexy grown-up, leaving Laurel in awe of her magnetism. “Did you just meet him when I was at the bar? Lady, you've got it going on,” she says. 

But then that final scene comes along and reverses the episode's entire stance in one frame. There’s Big, apparently back from Paris at a Hamptons party, holding hands with Natasha, his new and obviously young girlfriend. It’s a startling scene and a sad one, as Carrie shakily asks Big how old Natasha is. “26, 27,” he says vaguely, igniting an insecurity she lacked so visibly during the episode. 

The irony is that, much later, a 50-something woman echoes that same insecurity to a 38-year-old Carrie, who is involved with a much older man, but more on that later. 

Season 3, episode 9: “Easy Come, Easy Go” (2000)

The clichéd idea of wanting what you can’t have is played up in this episode, and—even if you’re a Mr. Big apologist—it’s probably hard to classify his behavior during this episode as anything other than reprehensible. Big is now married to Natasha and Carrie is with Aidan, although she’s torn about his constant availability and general affability, i.e., she doesn’t understand how to exist in a healthy relationship after two years of adrenaline-fueled push-and-pull with Big. But she does seem happy at the top of the episode, joking around with Aidan at a furniture showcase until—yup, we’re here again—Big shows up with Natasha. 

The scene in which the two men meet is brief but—to me—eternally memorable. Big looks shell-shocked, and Aidan is friendly but grows visibly confused about who these two people making Carrie so nervous are. Later, Big sidles up to Carrie, whiskey in hand and—highlighted by some smart, circular camera work—proceeds to not only mock Aidan but drunkenly tell Carrie his marriage isn’t working. “I’m getting out,” he slurs, but Carrie keeps her cool and dismisses him. Although he calls her later to tell her he didn’t mean what he said, the allure of knowing Carrie is with somebody else crushes Big’s ego and he follows her to the hotel she’s (conveniently) writing in as poor Aidan renovates her apartment, and an affair is born. 

I’d argue the episode is crucial because it cements Carrie’s status as a flawed antihero whose desire for love isn't an amorphous, romantic personality trait: It's always been all about Big, and nobody can measure up. “My mind was yelling how angry I was, but my heart…,” she says when they come together again. This is also the episode in which marriage-starved Charlotte essentially proposes to herself, thereby getting what she thinks she wants with seemingly perfect Trey. We all know how that turned out. 

Season 4, episode 15: “Change of a Dress” (2001)

While the season-four finale, “I Heart NY,” is widely considered one of show's best—it aired five months after 9/11 and signifies new beginnings by having Big leave the city for Napa and Miranda give birth to her son, Brady—“Change of a Dress” is important for our characters but also for viewers who might be ambivalent about committing to predictable stages of life that often accompany growing up. 

Carrie—newly engaged to Aidan, with whom she reconciled with earlier in the season—refuses to wear her ring on her finger and panics every time her upcoming wedding is brought up. It's obvious Carrie’s crippling anxiety doesn’t have to do with marriage itself, but the fact that she doesn’t want to spend her life with anyone but Big, no matter how perfect and stable this version of Aidan is. “I'm missing the bride gene,” she says, which we later know to be categorically untrue given the rigmarole around her wedding in the first movie, a wedding that that was so over-the-top Big stepped into Carrie's season-four shoes and became the one to reject the idea of marriage. 

Aidan assumes she just needs time, but he isn't willing to wait too long—he’s still feeling the burn of Carrie’s Big affair and wants to make it official. By the end of the episode, he’s sleeping in the spare apartment, and Carrie’s voice-over tells us he moves out the next day.  

Miranda's storyline is undeniably relatable for women who want or have children but who don't possess the “mommy” gene society demands. “Everyone else is glowing about my pregnancy. When will I?” Miranda asks, after faking excitement during a sonogram during which she finds out she's having a boy. 

Other new stages that come with growing up the episode touches on: divorce, in Charlotte's case, and letting yourself be vulnerable, as Samantha is trying to do with Richard. 

Season 5, episode 1: “Anchors Away” (2002)

Season five is a tricky one. It's almost 50% shorter than other seasons, each episode has a quiet sadness to it, and the women seems lonelier and noticeably more disoriented, likely because each episode was shot soon after September 11, 2001 and the series wanted to respectfully acknowledge the pain the city—and America—was still feeling. “Anchors Away” isn't a classic, but it's hard not to feel a pang watching it, especially when—after a Fleet Week party—Carrie ends the episode defending her city to the charming Southern Navy officer who says it's too crowded and too dirty. “I can’t have nobody talking shit about my boyfriend,” she says as she leaves the party, the lights of Times Square shimmering as we fade out. 

Season 6A, episode 9, “A Woman's Right to Shoes” (2003)

If this episode were a novel written in 1941, its title would be Carrie and the Mystery of the Stolen Manolos, but look closely and the silly through line is actually vital to the series, to Carrie's character, and also to a 2003 New York City.

Why it’s pivotal: First of all, praise God that this episode was essentially a 28-minute hot take on lunatics who make people remove their shoes at an adult party. I’m strongly against this, but since we’re dealing with a germ-propelled pandemic at the moment, I’ll back off. 

Carrie's ongoing awareness of being single as the world moves around her is magnified when her designer shoes get lifted at a house party. When she confronts the host, Kyra offers to pay for them—until Carrie tells her they cost $485. “That’s insane,” Kyra says, offering her $200. When Carrie points out that Kyra used to buy Manolos, the response is cutting: “Yeah, before I had a real life...but Chuck and I have responsibilities now—kids, houses.”

“I have a real life,” a wounded Carrie sputters. The tables turn when a fed-up Carrie “registers” at Manolo Blahnik for the shoes and the saleswoman scolds Kyra for her wild children. The opposing perspectives—Carrie’s being that a single woman could consider possessions as satisfying as children and Kyra’s being that being a mother trumps all frivolity—feels on point. 

With this episode, SATC also nailed the newfound bougie “buggy boom” Manhattan was starting to see in 2003. In season one we saw satellite friend Lainie move to the suburbs, because that’s what city people did when they had families. By season six, choosing to remain in the city after having kids started to become a status symbol, and Kyra and Chuck were written as cartoonish yuppies with a downtown loft, three kids (!), and a Hamptons house. Listen closely and you’ll hear razor-sharp background chatter while Carrie looks for her missing shoes about “the amazing house in Sag.” (“We got the house, but we couldn't get a table at Nick and Toni's for the rest of the summer!” Kyra crows, the stray, stoned party guests roaring with laughter.)

“A Woman's Right to Shoes" is pivotal for its shortcomings, as well. It was indisputably too late in the game for the series to address the lack of people of color onscreen in a meaningful way, especially given the fact that almost every single episode takes place in New York City, and it’s a shame they used Blair Underwood’s wonderful Robert as a romantic foil—a “hot Black doctor” as Samantha cringily calls him—that eventually helps Miranda come to terms with her love for Steve, despite Robert's seemingly real feelings for her. 

Season 6B, episode 18, “Splat!” (2004)

Is it heavy-handed in its messaging? Yes. Is it also one of the most iconic episodes of the series? Also yes.

This is the final straw in Carrie’s internal struggle with singledom. Now almost 40, she experiences an overabundance of scenarios throughout this episode telegraphing to her that it’s time to flee to Paris with Aleksander Petrovsky, her older celebrity-artist boyfriend. The Paris invitation, while not relatable to most real women, brings things full circle: After a satisfying arc in season two during which Carrie and Big are finally finding their groove, he scurries off to Paris without telling her. In “Splat!,” Carrie is torn about leaving New York, but the invitation to go to Paris is a novelty gift, one that says, “My new boyfriend isn’t withholding like my last one,” despite plenty of evidence to the contrary. 

The eventual decision to flee with Petrovsky comes after a series of hilariously unambiguous events, including when Carrie’s former boss at Vogue, 50-something Enid Frick (Candice Bergen) delivers a searing monologue about what it’s like being single after a certain age while confronting Carrie about dating fellow 50-something Petrovsky. (I’m personally shocked that Vetements never slapped “Why are you swimming in my wading pool?” across a hoodie.) But we’re also given the character of Lexi, a tragic overgrown party girl and obvious proxy for Carrie if she decides to stay in New York and be single. We all know what happens to her: In a cocaine-induced rant, she falls out a window...and dies. “Ladies, if you are single in New York after a certain age, there is nowhere to go but down,” says Carrie at Lexi’s funeral. And so her future has been decided for her with all the subtlety of a two-by-four. 

Before Lexi’s demise, Petrovsky throws a dinner party for all Carrie’s friends—probably the best ensemble scene in the series—after having dismissed them in the previous episode. Each friend is so fully themselves, and Carrie wants to laugh at the vibrator jokes and she wants to explain to the group exactly what type of art her boyfriend does but she also sees the people closest to her through Petrovsky’s pretension and retreats. But the dinner shows her something shocking: Nobody in her life—Samantha included—is single anymore.

Perrie Samotin is Glamour's digital director and the host of the podcast What I Wore When.