Rewatching Sex And The City In My 30s—And It’s Time To Admit I Got It All Wrong

It’s been nearly 30 years since Carrie Bradshaw met “Mr. Big” for the first time in New York City.

HBO’s Sex and the City, which ran from 1998 to 2004, was a cultural staple. A show that felt like the perfect vibe of being with your girlfriends and dating in the big city.

We could live vicariously through Carrie and her friends. And of course, the men they loved along the way.

Sex and the City premiered when I was in elementary school, but I didn’t see a single episode until my teens.

Since then, it’s been a casual, periodic rewatch. A series that carries throughout life’s biggest moments, from first apartments to first loves.

And to first breakups.

You could feel inspired like hopeless romantic Charlotte, or a cynic like Miranda.

Carefree and confident like Samantha. Or, in most cases, just trying to figure out all the chaos like Carrie. The girls made it a great time to dish and dissect all the dating woes.

It’s been a year since the disastrous run of And Just Like That… Season 3, closing the book on the franchise at large.

No amount of nostalgia could save the damage this spinoff has done.

As I’m now experiencing life in my mid-thirties, the same as the characters on Sex and the City, it felt like time for a rewatch. Rediscovering why we all fell in love with the series in the first place.

But as seasons passed, the startling reality became very clear: these weren’t the cool girls that once filled the aspirations of being a 20-/30-something in the city.

Instead, the older cool girls felt more like peers—friends that you could relate to, and ones that were in serious need of advice.

Age and life experience are interesting things.

Life can teach you so much. It can give you clarity to really look at a situation and break down the root of the problem.

For example, the Mr. Big situation would’ve been handled very differently, regardless of it being in the late 90s/early 2000s.

This latest rewatch, one that came after several years, revealed a new side to the friend group. The challenges they faced in dating, and how they, as well as their partners, played a part in everything.

Sex and the City feels less like a guilty pleasure now, but more like a frustrating return.

I Couldn’t Help But Wonder: “Why, Carrie?”

Carrie Bradshaw is a messy character. In many cases, she is the architect of her own chaos.

A surprising revelation about Carrie was how judgmental she was about everything.

She is a cynic with preconceived notions she lords over everyone. Judgments about those who live in New York, notions about dating, and the standards she expects others to follow but not herself.

For a lifestyle and sex columnist, she’s very narrow-minded about dating in general.

Sure, it’s been well-known among fans how self-involved Carrie is, especially in her friend group. It’s just surprising that her And Just Like That… attitude stems all the way back to Sex and the City Season 1.

Carrie’s dating life is even more divisive than the great Rory debate of Dean vs. Jess vs. Logan on Gilmore Girls.

They’re the big loves that guide the franchise. The iconic moments that fill all the one-liners.

But it’s in those big moments that we see the nuances we missed before.

For instance, Carrie’s romance with writer Jack Berger was doomed from the start. He’s an insecure man who only wanted someone who didn’t challenge him or help him grow.

In some ways, he’s the other side of Carrie’s same coin.

So, it’s surprising that Carrie felt “blindsided” that he broke up with her. Regardless of it being the Post-it note, she had been ready to leave a long time.

This is a decision of ego vs. love.

Jack Berger is all red flags, and he was a major problem. They both contributed to drawing out a relationship that had no place lasting.

In contrast, Carrie deserves credit for walking away from Aleksandr Petrovsky.

He lovebombed her, plain and simple. He’s an egotistical artist who didn’t love her; he only wanted a companion on his arm.

All those previous romantic gestures now look like manipulation tactics. These big, grand actions were to sweep her off her feet, but they were to lure her into his storm.

Big loves, bigger decisions

Carrie’s biggest loves, Mr. Big and Aidan, look messier than ever now. Even without the movies and And Just Like That… in the mix.

Carrie’s first relationship with Mr. Big imploded because of her expectations.

Let’s not forget: they only dated about a year the first time. They never lived together, hadn’t met family members, or crossed many of the big moments.

Their relationship progressed at a balanced pace. But Carrie wanted everything, all-in, and a confirmed forever within a year.

Even Mr. Big, who later debated whether he might not get married again, had warmed up to the idea of marrying Carrie.

If their relationship had kept the first time, while destructive it became, it could’ve led to the same place where the series finished.

The problem, however, comes in every iteration after that.

Regardless of whether it’s Mr. Big or Aidan, these relationships are one poor decision after the other. And these are choices brought on by both of them.

Like, Mr. Big only wanted to use Carrie until he realized he might lose her forever. Aidan was Carrie’s rebound man, and deep down, he knew and was fine with it until he wasn’t.

Carrie never should’ve gotten back together with Aidan the second time. She never wanted to marry him.

And Carrie is just as bad as Mr. Big because she knowingly went into that affair.

Mr. Big cheated on his wife, Natasha, but Carrie knew what that betrayal meant for everyone: Natasha, Aidan, and all her friends.

We could go on and on. In reality, Carrie’s relationships with Mr. Big and Aidan should’ve ended a long time ago, and the signs were all there that neither would truly work in the long term.

Carrie’s voiceover makes it all seem like a philosophical dating journey. However, these were all self-aware decisions made by adults.

Samantha Will Try Anything

Meanwhile, the allure and excitement of Samantha wore off this time.

Don’t get me wrong, Samantha is cool, confident, and knows exactly what she wants. Her self-esteem and confidence are very desirable!

However, did anyone realize how little Samantha cared about everyone else?

No, not about her friends–she cared about them the most, besides herself. It’s about all the other “insignificant” people who get in the way of pleasure and fun.

They mean nothing to her.

It’s surprising how many times Samantha was the other woman.

She didn’t care if she ruined someone’s relationship. In her eyes, it wasn’t her couple, so it wasn’t her problem. Regardless of whether she knew she was the other woman.

In the Carrie & Mr. Big affair, she’s encouraging Carrie to cheat. She wants her to have fun, dismissing any concerns or hurt Natasha could feel.

Samantha is all pleasure and no consequences.

It’s disappointing to unpack this deeper side to her. Thankfully, she’s grown the most throughout the franchise, experiencing new sides to love and the pain of being cheated on (Richard is the worst!).

But it’s shocking how that cool and confident side also stems from a self-involved mindset.

Miranda chooses mayhem

Among the friend group, Miranda’s path is the least surprising.

In every rewatch, she’s built a wall that both keeps love away and gives herself a pedestal to criticize it.

She is cynical. To make matters worse, she and Carrie feed off each other, reinforcing their negative judgments.

For every time she’s wondered about love, there are at least nine times when she’s had a negative opinion about something or someone.

Sure, it’s a defense mechanism, and she’s taught herself to be strong. It can also be said that she gravitated to it.

Like with Skipper and Steve. I forgot how on-again, off-again her mindset toward them was.

Miranda was so decisive that neither was the right match for her.

She knew in her bones that they didn’t align with her life goals or with who she was as a person. Yet, she kept reigniting the romance, almost expecting different results.

We’ve all had friends like Miranda: someone who’s smart and level-headed, yet kept making the same mistakes. This friend could also be who you see yourself as.

It’s surprising how much Miranda contributed to her dating disasters. Sometimes, even more detrimental than Carrie.

Skipper and Steve were no better. We’re not giving them a pass, and rightfully, they don’t deserve it.

They jumped right back in, even if they knew how toxic things had been. And even if they were in relationships with other people. Everyone gravitated back together.

Their dynamics felt like a toxic cycle.

A continuous return to what felt safe, or choosing “the devil they know” because of old feelings. Skipper and Steve created, if not also enabled, the messy dynamics during their time with Miranda.

Charlotte Always Wanted True Love

On the other hand, rewatches kept Charlotte consistent throughout. In most cases, her goal stayed the same: she wanted to get married and find love.

The biggest surprise this time, however, was realizing how much Charlotte rushed the process.

She was so determined to get her “Happily Ever After” that she looked past every red flag to see the end goal. Or she rushed in before communicating a plan with her partner.

Sometimes, she would be 100% right (Trey), and other times, it could’ve been permanently disastrous (Harry).

For those who get married quickly, to each their own. When you know, you know!

In Charlotte’s case, despite the implosion of her marriage with Trey, she worked through all the discoveries and issues. He didn’t want to be married or have kids, and that’s not something she could’ve ever known beforehand.

Their goals didn’t align anymore.

Charlotte deserves all the kudos for respecting her boundaries and sticking to what she wants, and how she wants to be treated.

Trey barely treated her like his wife, like a loving partner in their marriage. He’s 100% at fault for being the root of all their problems.

Harry, on the other hand, is a lucky break that everything worked out.

As mentioned above, Charlotte rushed in and expected a lot so soon. The original assumption about their timeline was so far off; they were barely together before she converted and expected marriage.

Harry and Charlotte should’ve sat down first and communicated a plan.

The fairytale romance is a beautiful story, but it takes more than just overcoming barriers. There are relationship dynamics and shared visions, ones that Charlotte wanted to bypass.

If any couple deserves to survive the franchise, Charlotte and Harry did. Their love is just too cute!

Let’s keep the conversation going — it’s the only way the good stuff survives.

Do you agree or disagree with the romances of Sex and the City? Is there one you think people are getting wrong?

Which character has surprised you during your rewatches?

Share your thoughts in the comments below, and invite another fan to join the conversation.

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