Let’s be real. If you’re a fan, you know exactly what I’m talking about. Mention season 5 of sex and the city to any die-hard viewer, and you’ll likely get a polarizing reaction. It’s the "short" season. The "baby" season. The season where Carrie Bradshaw’s hair reached peak chaos and the fashion went from "experimental" to "I’m wearing a bird on my head."
But there is a very specific reason why these eight episodes feel so vastly different from the glossy, high-fashion romp we saw in season 4 or the heavy emotional lifting of the final season 6.
Sarah Jessica Parker was pregnant.
That single biological fact dictated everything about the production. It shortened the episode count, it gave us those infamous empire-waist dresses, and it fundamentally shifted the energy of the show. While many critics at the time—and fans on Reddit today—dismiss it as a filler year, I’d argue it’s actually the most honest the show ever got. It’s messy. It’s awkward. It’s basically the "awkward teenage years" of a show that was otherwise incredibly polished.
The Big Red Flag: Why the vibes were off in Season 5
Most people remember the show for the "Heels and Martinis" lifestyle. By the time we hit season 5 of sex and the city, the girls weren't just looking for Mr. Big; they were looking for themselves in a post-9/11 New York that felt a little quieter and a lot more somber.
The premiere, "Anchors Away," is a love letter to New York City. It had to be. Filmed not long after the Twin Towers fell, the production team, led by Michael Patrick King, felt a massive responsibility to show the city’s resilience. This wasn't just about Carrie’s dating life anymore. It was about the city itself as the fifth character.
However, the "vibe shift" wasn't just about the setting. Carrie was single. Miranda was a new mom. Samantha was, well, Samantha, but Charlotte was reeling from her divorce with Trey. The quartet wasn't doing the four-person brunch as much. The synergy was fractured. Honestly, it felt a little lonely.
That hair and the "Carrie" problem
Can we talk about the bob? SJP’s short, curly bob in this season is a character in itself. Some fans love the freshness; others see it as a symbol of the show losing its way. It’s emblematic of the whole season: a bit frantic, a bit experimental, and not quite sure where it’s going.
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Carrie spends a lot of this season being, frankly, a bit of a mess. She’s obsessing over her book launch. She’s worrying about her "light." She’s wandering around the Atlantic City boardwalk in a giant coat trying to find a spark that isn't there. It’s uncomfortable to watch because Carrie is usually the one with the plan—or at least the one with the most interesting problem. Here, she’s just... drifting.
The Miranda Factor: Realism hits the fan
While Carrie was floating, Miranda Hobbes was anchored to the ground by a screaming infant. If you want to know what actually makes season 5 of sex and the city worth a rewatch, it’s Cynthia Nixon’s performance.
This was the first time a major "glamour" show depicted the absolute, soul-crushing exhaustion of new motherhood without a sugary coating.
- The "Magda" moments were gold.
- The scene where Miranda can't get Brady to stop crying and she just loses it? That’s 100% pure, unadulterated reality.
- She felt fat. She felt disconnected from the "sexy" world of her friends.
- She was eating chocolate cake out of the trash (wait, that was season 4, but the vibe carried over).
The show didn't shy away from the fact that a baby changes the group dynamic. In the episode "Plus One is the Loneliest Number," we see the stark contrast between the single life and the "mom" life. It’s one of the few times the show acknowledges that maybe, just maybe, you can’t have it all at the exact same time.
Samantha and the Richard Wright fallout
Samantha Jones is usually the comic relief or the sexual pioneer. In season 5 of sex and the city, she’s actually the one dealing with the most grounded emotional stakes. She got her heart broken by Richard Wright.
Watching Samantha—the woman who "doesn't do" relationships—try to navigate the aftermath of infidelity was fascinating. We saw her spy on him with a wig. We saw her struggle with the concept of trust. It humanized her in a way that the earlier seasons didn't.
The Atlantic City Trip
The episode "Luck Be a Lady" is probably the quintessential season 5 experience. The girls go to Atlantic City. It’s depressing. It’s gray. Samantha thinks Richard is cheating. Charlotte is worried she's the "old maid." Carrie is trying to force a "fun girl" vibe that just isn't happening.
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It’s an episode about realizing that you’re getting older and the things that used to be easy—like a weekend getaway with the girls—now feel like work. It’s not "escapism" TV. It’s "holding up a mirror" TV. And for a lot of people, that’s not what they signed up for.
Why the critics were wrong about the "Short" season
Because there were only eight episodes, the pacing is weird. Usually, a season has room to breathe—roughly 18 to 20 episodes to build an arc. Here, we get the book launch, the trip to San Francisco, and then... it just ends.
But there’s a secret benefit to this. There is zero filler.
Every scene in season 5 of sex and the city has to move the needle. We see Charlotte meet Harry Goldenblatt. This is arguably the most important thing to happen in the entire series. If we had a full 20-episode season, Harry might have been just another "bad date" in a string of many. Because the season was compressed, their relationship had to be fast-tracked, which actually mirrored the intensity of their connection.
Harry was the antithesis of the "Park Avenue Prince" Charlotte thought she wanted. He was sweaty, he was loud, and he was perfect. Without the constraints of season 5, we might not have gotten to their "real" love story as quickly.
Key episodes you shouldn't skip
If you’re doing a marathon and thinking about skipping this year, don't. Just watch these three. They contain the DNA of what the show eventually became in the movies and the revival.
- Anchors Away (Episode 1): The fashion is insane (that sailor outfit?), but the sentiment is real. It’s the "reintroduction" to a New York that felt very fragile.
- I Love a Charade (Episode 8): The season finale. It takes place in the Hamptons. It’s where Bobby Fine gets married and where Charlotte finally admits she has feelings for Harry. It’s the most "classic" feeling episode of the bunch.
- Cover Girl (Episode 4): This is the one where Carrie’s book cover becomes a major plot point. It’s a great look at the "career woman" aspect of the show which sometimes got buried under the dating drama.
The Fashion: A transition period
Patricia Field, the legendary costume designer, had a tough job this season. Hiding a pregnancy is one thing; making it look high-fashion is another.
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We saw a lot of:
- Huge Hermes Birkin bags held strategically in front of the stomach.
- Flowy, bohemian tops that were a departure from the tight Dior saddles of previous years.
- Over-the-top accessories to draw the eye upward toward the face.
It created a "shabby chic" look for Carrie that defined the early 2000s. It wasn't as sleek as the "Paris" era of season 6, but it was influential in its own quirky way.
What most people get wrong about the ending
People think season 5 ends on a cliffhanger. It doesn't. It ends on a note of growth.
When Carrie is walking down the street at the end of "I Love a Charade," she’s not looking for a man. She’s confident in her success as an author. Miranda is settling into motherhood. Samantha is back to her confident self. And Charlotte is on the path to a religion and a man she never expected.
It’s the first time the show suggested that "happily ever after" didn't have to look like a diamond ring and a white dress. It could look like a sweaty lawyer and a baby in a Brooklyn apartment.
Actionable takeaways for your next rewatch
To truly appreciate season 5 of sex and the city, you have to change how you watch it. Don't look for the Big vs. Aidan drama. It’s not there.
- Watch for the Harry/Charlotte origin story: It’s one of the best-written "mismatched" romances in TV history. Pay attention to how the show slowly strips away Charlotte’s superficiality.
- Focus on the New York tributes: Look at the background shots. The show was filming in a city that was healing, and you can feel that reverence in the cinematography.
- Analyze the "Work" arcs: This season is more about the women’s careers—Carrie’s book, Samantha’s PR firm, Miranda’s law partner struggles—than almost any other. It’s a great blueprint for how to handle professional identity in your 30s.
- Embrace the brevity: Treat it like a limited miniseries. It’s a bridge between the "dating" show of the 90s and the "relationship" show of the 2000s.
If you view this season as a transition instead of a destination, the weirdness starts to make sense. It’s not the best season, but it might be the most human one. It’s the season where the characters finally grew up, whether they wanted to or not.
Next Step: Watch the season 5 finale "I Love a Charade" and the season 6 premiere "To Market, To Market" back-to-back. You’ll see exactly how the momentum from the short season perfectly set up the high-stakes drama of the show’s final run.