It’s been over twenty-five years. Seriously. If you think about the math, it’s a little terrifying that Carrie Bradshaw first stepped onto a New York City sidewalk in her tutu back in June 1998. When we talk about the Sex and the City years, we aren’t just talking about a time slot on HBO. We are talking about a very specific, pre-social media era of Manhattan that feels like a fever dream now.
New York was different. The dating world was analog. People actually had to call each other on landlines and leave messages on tape machines. If you missed a call, you missed a date. It’s wild to look back at those early seasons and realize how much the show relied on the physical absence of people. That’s something Gen Z, currently discovering the show on streaming, finds almost alien.
When exactly were the Sex and the City years?
The show didn't just appear out of thin air; it was born from Candace Bushnell’s columns in The New York Observer. The actual series ran from 1998 to 2004. Six seasons. Ninety-four episodes.
But the timeline is actually kind of messy.
While the show aired over six years, the internal logic of the characters' lives often stretched or compressed time to fit the emotional arc of the week. For example, Carrie’s age is a bit of a moving target early on. In the pilot, she’s supposedly thirty-something, but the show’s "present day" always felt untethered from a strict calendar until the later seasons when big milestones—like Miranda having Brady or Charlotte’s first marriage to Trey MacDougal—started forcing a more linear progression.
The show basically captures the transition from the late-90s "Cool Britannia" influence into the post-9/11 landscape of the early 2000s. It’s worth noting that the show famously chose not to address 9/11 directly in the plot, but the shift in tone is visible. The colors got warmer. The fashion got more expensive. The city felt more like a sanctuary and less like a playground.
Breaking down the eras
You can generally split the Sex and the City years into three distinct phases:
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- The Gritty Indie Phase (1998-1999): This is seasons one and two. The lighting is harsher. Carrie talks to the camera (thankfully they stopped that). It feels more like a documentary about dating and less like a fashion show.
- The Golden Era (2000-2002): Seasons three and four. This is when the show became a global phenomenon. This is the Aidan vs. Big peak. It’s when the puns got faster and the Cosmopolitans were everywhere.
- The High-Fashion Drama Phase (2003-2004): The final two seasons. The stakes got real. Cancer, infertility, moving to Paris. The costumes by Patricia Field became high art, and the budget clearly exploded.
Honestly, the way the show aged with its audience is why it stuck. Most sitcoms just stay the same age forever (looking at you, Friends), but these women actually got older. They dealt with the physical and social reality of aging in a city that prizes youth above almost everything else.
The logic of the 1990s dating scene
Think about the "Secret Sex" episode or the one where Carrie dates the "New Power Lesbian." These stories worked because information was scarce. You couldn't Google your date. You couldn't check their Instagram stories to see if they were actually at dinner with their "cousin."
During the Sex and the City years, the mystery was part of the problem. And the fun.
The "Manhattan dating" lexicon—ghosting (though they called it "the mid-week fade"), the "waiting by the phone" anxiety, the "is he a freak?" vetting process—it was all managed through brunch debriefs. That’s why the diner scenes were the heart of the show. Those four women were each other’s search engines. They were the original Reddit thread for "Am I the Drama?"
Darren Star and later Michael Patrick King understood that the city was the fifth character, but the dialogue was the engine. If you listen to the cadence of the early seasons, it’s fast. It’s snappy. It’s cynical in a way that feels very New York. As the years went on, that cynicism softened into something more sentimental, which some fans loved and others... well, others missed the bite of the first twenty episodes.
Why the math of the show's timeline matters
If we look at the specific years, we see a massive shift in how women were "allowed" to exist on TV.
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In 1998, a show about four women over thirty talking explicitly about their sex lives was revolutionary. By 2004, it was the blueprint. But there are some weird inconsistencies if you’re a total nerd about the timeline. For instance, in Season 1, Carrie mentions she’s been in the city for ten years. If she moved there in the mid-80s, her evolution from a "club girl" to a "Vogue contributor" is a very specific New York trajectory that mirrors the city’s own gentrification.
The show's "years" also represent a peak in magazine culture. Carrie’s job as a columnist was a real, high-status career back then. You could actually afford a (rent-controlled) apartment on the Upper East Side by writing one column a week.
Okay, maybe not really. Even back then, fans pointed out that Carrie’s shoe habit—which she famously calculated had cost her $40,000 at one point—didn't match her paycheck. But the Sex and the City years were about aspiration, not necessarily a budget audit. It was about the vibe of being independent when that was still a relatively fresh narrative for TV.
The impact of 2004 and the "End"
When the series ended in February 2004, it felt like the end of an era for New York too. The city was changing. The Meatpacking District, where Samantha lived, was becoming a mall. The rough edges were being sanded off.
The finale, "An American Girl in Paris," took Carrie out of her element to show that she only truly made sense in Manhattan. It was a polarizing ending. Some people hated that she ended up with Big. Others felt like it was the only way to close the loop on the six-year cycle.
What’s interesting is how the "years" didn't actually end in 2004. We had the 2008 movie, the 2010 sequel (which we mostly try to forget), and now the And Just Like That era. But the original 1998–2004 run has a specific texture that can't be replicated. It’s the grain of the film. It’s the lack of iPhones. It’s the way people smoked in bars.
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Practical takeaways for the modern viewer
If you’re revisiting the series or watching it for the first time, keep a few things in mind to actually enjoy the historical context:
- Look at the background. The storefronts, the taxi cabs, the lack of Starbucks on every corner. It’s a time capsule of a pre-luxury-condo New York.
- Pay attention to the technology. From the massive "brick" cell phones in Season 1 to the Blackberry era later on, the show accidentally documented the tech revolution.
- Ignore the "money logic." If you try to figure out how they afford those clothes, you'll get a headache. Just accept it as a sartorial fairytale.
- Watch for the guest stars. Everyone from Bradley Cooper to Elizabeth Banks popped up before they were "anybody." It’s like a game of Hollywood Bingo.
- Notice the shift in "The City." The early seasons feature a lot of downtown, darker locations. The later seasons are almost exclusively "Gold Coast" Manhattan—bright, shiny, and expensive.
The Sex and the City years were a bridge between the 20th and 21st centuries. They defined a specific kind of female friendship that hadn't been seen on screen before—one where the "happy ending" wasn't necessarily the guy, but the three women sitting across from you at the table. Even with all its flaws, the lack of diversity, and the questionable financial choices, that core remains why people are still talking about it decades later.
If you want to understand the cultural shift, watch the pilot and the series finale back-to-back. The evolution isn't just in the hairstyles (though Carrie’s hair journey is an epic of its own); it’s in the way the characters stop looking for "the answer" to dating and start accepting that life is just a series of messy, expensive, and beautiful mistakes.
The real legacy of those years isn't the fashion or the drinks. It's the fact that for the first time, single women were the protagonists of their own lives, not just the sidekicks in someone else's. And honestly, that’s why the show still works. It wasn't about finding a man; it was about finding yourself in a city that's constantly trying to change you.
Stop worrying about whether the timeline makes perfect sense. It doesn't. New York time moves differently anyway. Just enjoy the ride through a version of the city that doesn't exist anymore, but still feels like home to anyone who’s ever been a little bit lost in their thirties.