The Best Sex and the City Episodes of All Time

According to me, an expert.

If you are a member of the cult of Carrie Bradshaw, you’re well aware that (HBO) Max’s Sex and the City reboot And Just Like That… recently returned for its second season. I have very mixed feelings about the new show, but I am of course watching it and will be throwing watch parties in its honor as long as it is on the air. Still, the new series has very little to do with the characters, spirit, and message of Sex and the City’s original run. The original world of the series was far more complex, messy, funny, and painful.

So, I invite you back to New York at the turn of the century. You can still smoke in restaurants. Everyone has a landline. Cabs and new boyfriends are around every corner, and Carrie Bradshaw can’t help but wonder if she’ll ever fall in love.

If you’re a fan, unafraid of spoilers, and due for a rewatch, please enjoy…

The 10 Best Sex and the City Episodes of All Time (In Order)

“One” Season 6, Episode 12

“One” highlights every character’s growth throughout the series: Brady’s first birthday party is the setting for Miranda and Steve’s heartwarming reconciliation, Samantha owns her age until trying to dye a grey pubic hair leaves her looking like “Bozo the Bush,” and Carrie begins dating her ever-controversial love interest Aleksandr Petrovsky aka “The Russian.” My favorite moment, however, is when Charlotte sets aside her grief and disappointment over a miscarriage to attend Brady’s birthday. Finding strength in Elizabeth Taylor: The E! True Hollywood Story, Charlotte triumphantly leaves the house in sunglasses and a pink dress. The small moment of strength represents a huge victory for her character and feels both honest and moving.

It’s so hard to fill the number one slot, but “One” sticks out in my mind as a series high point. It’s a beautiful portrait of friendship, love, loss, strength, uncertainty, and everything else Sex and the City is all about.

“My Motherboard Myself” Season 4, Episode 8

Every top ten list features “My Motherboard Myself,” and God, it’s good. Cynthia Nixon delivers the best dramatic performance of the series when Miranda deals with her mother’s unexpected death.

From the Bryant Park picnic opening to the closing funeral procession, this episode does not miss once. Carrie loses her mind about her laptop, Samantha can’t cum, and Charlotte becomes the “Martha Stewart of Death.” Samantha’s subplot in particular is a brilliant way of showing her character’s struggle to process her grief.

It’s an impeccable blend of comedy and pain in twenty-eight minutes. Rewatching the episode for this list made me cry.

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

A fan favorite, this episode features Carrie standing up for the validity of her life as a single woman.

When Carrie’s friend refuses to replace her Manolos that were stolen at a child’s birthday party because the shoes are too “extravagant,” Carrie finds herself wondering why she should be expected to financially support her married friend’s lifestyle with expensive wedding and baby shower gifts. It’s a fascinating question that blends the show’s capitalist themes with the personal. It’s ripe for critical analysis and remains culturally relevant.

“The Baby Shower” Season 1, Episode 10

A comedic masterpiece that I cannot do justice to in a recap. It’s the first episode of the series that explores pregnancy and shows Samantha Jones is a party-hosting inspiration. Friends, if you have sex on my futon, you buy it.

“Splat” Season 6, Episode 18

Another masterpiece! There is no other word for it. Carrie is deciding whether to ditch New York for a Paris fantasy with the Russian when the real star of this episode, Kristen Johnston’s aging party girl Lexi Featherston, delivers a killer monologue:

“When did everybody stop smoking? When did everybody pair off? This used to be the most exciting city in the world…now it’s nothing but smoking near a fucking open window. New York is over. O.V.E.R. Over. No one’s fun anymore. Whatever happened to fun? God. I’m so bored I could die.”

“I Heart NY” Season 4, Episode 18

Aired after 9/11 and dedicated to the city of New York, this episode is about transitions.

The primary storyline follows Big’s decision to leave New York and Carrie’s reluctance to let him go. There’s a melancholic and bittersweet mood that matches what the city was experiencing at that time. Carrie wants to have an incredible final night, but it’s one of the things where the timing just isn’t right. As our favorite couple meets their end, the friend group finds a new beginning in the birth of Miranda’s son.

Cue up “Moon River” and grab some new shoes for a Central Park carriage ride, as Carrie, Big, and New York say their goodbyes.

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

This episode dives into abortion when Miranda accidentally becomes pregnant at the same time Charlotte learns she likely can’t get pregnant. I watch A LOT of TV and this is among my favorite TV explorations of abortion (along with Veep and Sex Education). The episode’s title says it all. It’s always a difficult choice but once you make it there’s no point in shame or wondering what else you could have, would have, or should have done.

After Carrie and Samantha discuss their past abortions, Carrie finds herself unexpectedly anxious to tell Aiden she had one at twenty-two. It’s an interesting look at how (cis) men and women experience the issue differently. Carrie’s hookup from over a decade earlier hasn’t thought twice about what might have been, but Carrie’s carried the experience with her, and because it’s a part of her, it informs her present relationship. When Miranda is deciding whether she should go through with the procedure she asks how long it took for Carrie to feel normal again. Carrie replies, “Any day now.”

“Valley of the Twenty-Something Guys” Season 1, Episode 4

This episode is “a preview” of everything Sex and the City would become!

It shows how the series would pose weekly questions about sex and dating, for each character to offer an alternative perspective on. If Charlotte has anal sex, will she lose the power in the relationship, or is a hole really “just a hole?” “Valley of the Twenty-Something Guys” also highlights how the friendship between the four leads would become the heart of the series. Plus, the joke about 20-something guys’ apartments is spot on.

“They Shoot Single People, Don’t They?” Season 2, Episode 4

Are we single & fabulous question mark or single & fabulous exclamation point? Note that, “The question mark is hostile.”

With a guest appearance from a young Bradley Cooper and incredible use of a Dutch angle, this episode is the first of many to ask, “Is it better to fake it than be alone?” I still find the image of Carrie having a glass of wine all by herself at the end of the episode inspirational.

“The Agony and the Ex-Tacy” Season 4, Episode 1

“The Agony and the Ex-Tacy” is a mixed bag overall,¹ but it earns its spot on my list for having my favorite ten-minute sequence of the whole series.

At the end of this episode, Carrie is stood up at her 35th birthday dinner. In a hilarious and tragic sequence, we see her pay for her own cake, drop it, and have an all-around horrible night. When her friends arrive at her apartment late, Carrie admits to feeling alone without a man in her life. This prompts Charlotte to respond with the quote above.

In my mind, this moment is what the series is all about. Big may show up in a black town car after Carrie leaves her girls at the diner, but he’s not the one she’s honest with. Throughout the series, Carrie puts on a facade while dating, trying to be low-maintenance, cool, or more put-together than actually she is. It’s her friends who know the best and worst of her and love her anyway.

Honorable Mentions:

“Ex and the City” Season 2, Episode 18

Some people would call it sacrilege to keep this off my top ten list. It’s the quintessential Big-and-Carrie episode, but I don’t LOVE it as much as the others. Still, seeing Carrie quote The Way We Were in front of the Plaza Hotel is a defining moment of the series that sticks in any fan’s mind forever.

“The Ick Factor” Season 6, Episode 14

Miranda and Steve’s wedding is a rare heartfelt and hopeful celebration of love. There is no fear or “faking it” here. Miranda lets her cynical side go long enough to celebrate the family she’s found over six seasons. Coupled with the emotion of Samantha’s breast cancer diagnosis, any fan’s heart will be full by the end of this episode.

“All That Glitters” Season 4, Episode 11

In “All that Glitters” Charlotte’s marriage isn’t all gold. The fairytale she believed she’d found with Trey doesn’t pan out when Charlotte’s infertility becomes the final straw in a long line of compromises and differences.

As Trey and Charlotte pose for their Better Homes and Gardens photographs, Carrie describes in voice-over, “Trey had moved out by the time the magazine was on the stands. But all over America little girls in their mother’s pearls saw the picture and thought ‘That’s what I want.’” It’ll break your heart.

“I Love a Charade” Season 5, Episode 8

Nathan Lane as cabaret singer Bobby Fine offers the central question for this episode with his character’s trademark song “Is That All There Is?”

Like “Splat,” the season five finale shows the darker side of aging as a single woman. The fear sets in as our girls watch an older friend choose a sham marriage with a gay man rather than face life alone. It’s a funny and sad plotline that pushes each main character closer to their ultimate arc.

“What Goes Around Comes Around” Season 3, Episode 17

Robber: “Give me your bag!”

Carrie: “It’s a baguette!”

Carrie getting robbed at gunpoint and Miranda’s drunken date with a hot cop are scenes of comedic excellence. The episode features an important development between Charlotte and Trey and a cringe-worthy Samantha c-plot. BUT any fan knows that what makes this episode so iconic (aside from Carrie’s newspaper dress) is Natasha’s chills-inducing monologue:

“I'm sorry about it all. I'm sorry he moved to Paris and fell in love with me. I'm sorry that we ever got married. I'm sorry he cheated on me with you and I'm sorry that I pretended to ignore it for as long as I did. I'm sorry I found you in my apartment, fell down the stairs and broke my tooth. I'm very sorry that after much painful dental surgery this tooth is still a different color than this tooth. Finally, I'm sorry that you felt the need to come down here. Now, not only have you ruined my marriage, you’ve ruined my lunch.”

Scathing and deservedly so.

“Don’t Ask, Don’t Tell” Season 3, Episode 12

Charlotte’s first wedding is anything but magical. Again, the show excels in creating contrast when Charlotte’s dream WASP wedding is warped by the reveal of Trey’s impotence. As Charlotte enters a fraught marriage, Carrie finds herself out of a relationship when Aiden breakups up with her for cheating with Big.

“Twenty-Something Girls vs. Thirty-Something Women” Season 2, Episode 17

Titled from a section of Candace Bushnell’s book, this episode features a girls’ trip to the Hamptons and the introduction to Natasha! Call me crazy, but Carrie’s cowgirl glam get-up for the Hamptons end-of-summer bash is one of my favorite looks of the series.

Even More Honorable Mentions with My Favorite Gags of the Series:

“Luck Be an Old Lady” Season 5, Episode 3

The ladies hit Atlantic City, and Samantha delivers the ever-iconic breakup line, “I love you, but I love me more,” with such casual honesty.

“Plus One is the Loneliest Number” Season 5, Episode 5

Happy book release to Carrie Bradshaw! Any episode that features Candice Bergen’s Enid Frick is a cause for celebration, and she gets some great moments in this one.

“Where There’s Smoke” Season 3, Episode 1

Staten Island, disco dancing, drunk Charlotte, Roger Sterling. What’s not to love?

“The Big Journey” Season 5, Episode 7

I have to include this episode because I think Samantha and Carrie taking Amtrak from New York to L.A. is one of the funniest gags of the series.

“The Real Me” Season 4, Episode 2

Sex and the City is a show about a woman who falls on her face and is forced to get back up again. “The Real Me” makes that literal. Plus, we get a Margaret Cho guest spot!

“Take Me Out to the Ballgame” Season 2, Episode 1

Happy Yankees season! If only one could so easily snatch a date with the “hot new Yankee” in real life.

“Hot Child in the City” Season 3, Episode 15

Mrs. Adams (Carrie’s Boyfriend’s Mom): “Have you been smoking marijuana in my house?”

Wade (Carrie’s Boyfriend): “Carrie brought it.”

Mrs. Adams: “Is this true Carrie?”

Carrie: “Yes, it is Mrs. Adams. And I'm gonna take it with me when I leave.”

1. Samantha pined for a hot priest before Fleabag, just saying.