Mr. Big Was the Biggest Red Flag on Television, And I used to Date him...

If you were a millennial like me; or honestly, anyone who came of age while Sex and the City was taking over television, you couldn’t help but fall in love with the fabulousness of it all. Carrie Bradshaw’s tongue-in-cheek commentary on women’s sexuality and relationships made us feel seen. The fashion was aspirational, the friendships iconic, Manhattan itself felt like a fifth character, and somehow every brunch came with a life lesson wrapped in Manolos.

Twenty years ago, my gay best friend introduced me to the series. After meeting my first boyfriend, he declared with absolute certainty, “He’s soooo Mr. Big. And you’re soooo Carrie.” Reader, I am ashamed to admit… he sooooo was.

He was avoidant, emotionally unavailable, possessive, intoxicating, and perpetually just out of reach. Meanwhile, I was doing Olympic-level mental gymnastics trying to decode his cryptic behaviour, convinced that if I could just understand him, I’d finally unlock the love story I deserved.

The embarrassing part isn’t that I dated a Mr. Big. It’s that I romanticized the anxiety. The pining. The uncertainty. The waiting for texts. The dramatic reunions. The almosts.

Somewhere along the way, my generation confused emotional inconsistency with passion. We thought butterflies were chemistry when, in hindsight, they were often just our nervous systems screaming.

This year, I rewatched Sex and the City, expecting to feel the same nostalgia. As a fashion academic, a writer, and someone who has actually dated in Manhattan, I thought revisiting this cultural phenomenon would feel like meeting an old friend. Instead, I felt… heartbroken.

Not because the show wasn’t brilliant; it absolutely was. It changed television. It gave women permission to talk openly about sex, ambition, friendship, and pleasure in ways we hadn’t seen before.

But Carrie ending up with Mr. Big? That wasn’t the fairy tale I remembered. It was trauma with a designer wardrobe. Let’s recap. This is a man who spent years breadcrumbing her. He repeatedly kept one foot in and one foot out. He married someone else. He disappeared. He returned whenever it suited him. He resisted commitment until she was emotionally exhausted. And then, just when she was finally getting married, he abandoned her at the altar because… he panicked.

The image of Carrie hitting him with her bouquet outside the New York Public Library remains iconic.

The relationship? Less so. Viewed through the lens of attachment theory, Big is textbook avoidant. Carrie oscillates between confidence and anxious attachment, becoming increasingly preoccupied with his emotional availability. Their relationship becomes a cycle of pursuit, withdrawal, reunion, and relief.

The relief is mistaken for love, and that’s the trap. When someone keeps activating your abandonment wounds, finally “winning” them feels euphoric. But that’s not because they’re your soulmate. It’s because your nervous system mistakes intermittent reinforcement for intimacy. We called it chemistry.

Psychologists call it variable reward. No wonder we were addicted.

Back then, I celebrated when Carrie finally “got the guy.” It felt like validation that all the waiting, crying, analysing, and hoping had finally paid off. Now? It feels like a cautionary tale.

The irony is that when Big dies in And Just Like That…, I found myself feeling hopeful for Carrie again. Not because I wished him dead; that would be absurd, but because, for the first time in decades, she had the opportunity to rediscover herself outside a relationship that had always required her to shrink, chase, or compromise.

That’s hardly the happily ever after we’d been sold. Interestingly, the older I’ve become, the more I’ve realised Carrie isn’t even my favourite character anymore. Samantha Jones is. As a twenty-year-old, I thought Samantha was outrageous. As a thirty-something woman, I think she’s the protagonist. She is unapologetically herself. She owns her sexuality without apology or shame. She refuses to mould herself into someone else’s expectations. She leaves relationships that no longer serve her. She ages on her own terms. She knows exactly who she is.

Even Charlotte, whom I once dismissed as hopelessly traditional, earns my admiration now. She never pretends to want something she doesn’t. She values marriage, family, and romance, and she remains remarkably authentic to those values throughout the series.

Carrie, on the other hand, feels different on a rewatch. She’s witty, stylish, and charming, yes. But she also spends an astonishing amount of emotional energy revolving around men.

I found myself wishing someone had introduced her to therapy. To feminism beyond clever one-liners. To boundaries. To hobbies that didn’t involve obsessively dissecting her latest romantic crisis over cosmopolitans. Because here’s the thing no one told us in the early 2000s: The goal isn’t to be chosen by your Mr. Big. The goal is to become someone whose life is so full that Mr. Big either shows up consistently; or becomes a mildly entertaining anecdote you tell your friends over brunch.

Sex and the City didn’t lie about friendship. Miranda, Charlotte, Samantha, and Carrie remain one of television’s greatest portrayals of female friendship. It didn’t lie about fashion either. I’ll happily defend the tutu, the Fendi Baguette, and every outrageous Patricia Field ensemble until the day I die.

But it absolutely lied about love. Or perhaps, more accurately, we were too young to know the difference between longing and compatibility. The older I get, the less I want fireworks. Give me consistency. Give me peace. Give me someone who doesn’t make me decode text messages like they’re the Da Vinci Code.

Because the sex was fabulous. The city was magical. But Mr. Big? He should have stayed just that; a big red flag.

---

Photo © Sex and the City, HBO