Is the Cool Girl Really Dead, or Just Pretending?

I recently had dinner with a Friend who ordered one thing and received something entirely different.

Not a missing side of dressing or an accidental sprinkle of cheese. A completely different meal. When I suggested she tell our waiter, she looked at me like I was pressuring her to commit a felony in the middle of e. baldi.

“Nah, no reason to make the waiter feel bad.” So she spent the rest of dinner eating something she didn’t order and didn’t enjoy.

While I watched her push her food around (and realizing she was going to pay for this privilege), I started wondering: When did it become more uncomfortable to point out a mistake than to quietly live with one? How many things are we currently tolerating because we don’t want to seem difficult?

The Friend who never follows through. The coworker who adds more to our plates. The people we date who treat basic communication and respect like an optional and expensive subscription upgrade.

Someone else drops the ball. You pick it up. And then, for whatever reason, you apologize for noticing it was on the ground.

And we have a million names for this: easygoing, chill, low-maintenance. But if we know her most infamously as the Cool Girl.

We even gave the Cool Girl the full Barbie treatment: undeniably appealing and conveniently free of human needs. Her hobbies? Being agreeable, adaptable, unbothered, fine with whatever and down with whatever.

Her coolest feature? Requiring no maintenance whatsoever. Like a fake houseplant.

For years, we’ve been told she was the ultimate aspiration.

But, like every female star forced to maintain an impossible public image, what goes up must eventually come down.

We all know why “the old Taylor can’t come to the phone right now”.... And I’m proud to announce the Cool Girl is unavailable for the same reason.

And my men, please stick around. There are lessons in here for you too. Because while the Cool Girl might have started as a female dating stereotype, pretending not to care has become an equal-opportunity problem.

Before we bury her, let’s conduct a brief autopsy.

In her final years, she was spotted in our relationships, our workplaces, and our Friendships. And according to my findings, she wasn’t doing particularly well in any of them...

First up: Relationships. Historically, this is where we’ve been told we need Cool Girls the most.

The Cool Girl has been told that the most attractive thing she can do is not care. Including whether someone likes her (the Barbie and Ken dynamic ring any bells?).

Don’t text back quickly. Don’t ask where things are going. Don’t mention that you’d prefer plans made more than 45 minutes in advance.

And if a man disappears for two weeks before resurfacing with “hey stranger,” just pretend you also spent those three days in a remote location without cell service. You wouldn’t want him to think you noticed. Or worse, that you cared.

But, if you asked most women what they actually want in a partner? Someone who calls. Who makes plans. Who follows through. And who shows enthusiasm about getting together.

Basically, someone who is not chill about them.

I’m sorry to say that men are damned if they do and damned if they don’t. While women have been taught to idolize the Cool Girl, we’ve also been taught to idolize the opposite in men. Every rom-com gives us an unavailable woman and a man who pursues her, makes himself vulnerable first, and refuses to give up until we collectively swoon.

In real life, that same effort can either be super romantic or super not, depending on whether the feelings align. So showing interest has become a strategic liability for everyone. Two people can genuinely like each other but waste weeks pretending they have better things to do. We all want effort, but we’ll be damned if we’re caught making it first.

So why have we been encouraged to become the exact kind of person we would never want to date?

Relationship expert Shane Kohler talks a lot about why playing it cool can backfire. And if you insist you’re happy to “see where things go” when you’re secretly hoping they go somewhere specific, you are effectively marketing a version of yourself that does not exist. Congratulations: You are very chill and quietly miserable.

Eventually, you’ll say something. And the other person will wonder what happened to the laid-back girl they started dating. She was fictional. You spent three months pretending you had no needs and are shocked that someone actually believed you.

Nobody likes this plot twist. Especially the person who thought they found a girlfriend who could survive exclusively on vibes and the occasional text.

Conclusion: Chill (and quietly miserable).

Next up: Career.

Not to be confused with the Girlboss (she’s a very different creature), the Cool Girl doesn’t care about climbing the corporate ladder. She just somehow does it, usually while wearing impeccably tailored Khaite outerwear.

Emily in Paris is the perfect blueprint. Every week, Emily swoops in to save a crisis that has somehow stumped an entire agency of executives. The client is furious. A high-level campaign is falling apart. Her boss has no idea what to do. But don’t worry. Emily saw a croissant on the way to work and now has a revolutionary brand strategy. Crisis averted.

Do Cool Girls spend six hours researching and revising a project four times? We’ll never know. She must be brilliant without looking ambitious, prepared without appearing to prepare, and successful without revealing how hard she worked, how often she doubted herself, or how many times she failed.

Recently on Call Her Daddy, our Friend Alex Cooper examined why trying hard has somehow become more embarrassing than pretending success just happened. Apparently, it’s no longer enough to be good at your job. You also have to act like it requires no effort. Duke University named this “effortless perfection.” Stanford calls it “duck syndrome.” Calm above water but paddling like hell underneath.

Of course, natural talent goes a long way. So does being in the right room at the right time.

But neither of those can carry an entire career without work, grit, and help. When all anyone sees is the polished result, they assume the process was smooth and then compare your invisible effort to their very visible struggle. They wonder why the same success feels so much harder for them.

The better you get at hiding the work, the less work everyone assumes it takes. And your reward for making everything look manageable is more to manage in secret.

In conclusion: I’m exhausted for her, and for everyone comparing themselves to her. And finally: Friendship.

In Friendships, the Cool Girl comes in two editions.

Similar to dating, the first is the low-maintenance Friend. She doesn’t care about unanswered texts or canceled plans.

At least, that’s what she says.

Chanté Joseph wrote about this trap for British Vogue last year (queen has always been ahead of her time). She asked for little and expected even less because expecting less felt safer than admitting she wanted more from her Friends. It worked. Nobody could disappoint her because nobody was required to show up. Small catch: they also stopped being close.

Then there’s the other Cool Girl we’ve all tried being Friends with. She isn’t afraid of needing people, she’s just very busy making sure everyone knows how little she needs them. She’s terrible at texting. Impossible to schedule dinner with. She cancels plans almost religiously because “something came up,” then always reappears two months later with “I’m the worst!” (as if identifying the problem counts as fixing it).

She wears her chronic unavailability like a badge of honor. She’s booked. She’s thriving. And nobody is receiving much of her time.

And I’m not even going to pretend this works the same way with you dudes. I fully believe in the saying that female Friendships happen face-to-face while male Friendships happen side-by-side.

Women can chat over dinner at Seline about everything that’s happened that week, including how they feel and what their moms think about it. Men can catch a Lakers game, exchange six words, and leave knowing they had a great catch-up. You may or may not know what your best Friend does for work, but you know exactly who he’s starting in fantasy this week. Even side-by-side Friendships require occasionally showing up beside someone.

Back to our two Cool Girls. One makes herself smaller to keep her Friends. The other makes her Friends feel smaller to keep herself cool. And both treat caring like an embarrassing amount of effort.

In conclusion: One is exhausted from pretending she doesn’t need anyone. The other is just exhausting.

Cause of death seems to be quiet misery and exhaustion across the board. Because the problem with “low-maintenance” is that it usually means doing all the maintenance yourself, in every category.

And if the Cool Girl really is dead, why is everyone still obsessed with certain Cool Girl archetypes like Carolyn Bessette-Kennedy, or even SATC’s fictional Samantha Jones...

Maybe because it isn’t the Cool Girl that’s dead. Maybe trying to perform like one is...

A recent Vogue piece (yep I’m citing two Vogue pieces like an academic journal) makes the case that the way Carolyn Bessette-Kennedy is portrayed in Love Story represents the truest kind of Cool Girl. She isn’t suppressing herself to win a man. She knows her value—and apparently, even a Kennedy can be expected to make an effort. At the same time, she was very vocal about things she was not cool with. Which is really cool, because having boundaries is not the same as pretending you don’t have needs.

There’s a fine line between what you’re genuinely cool with and the things you’re just pretending to be cool with.

And Samantha? She genuinely didn’t want traditional relationships, openly cared about her career, and dropped everything for her Friends. She wasn’t pretending not to care. She was just very clear about what—and whom—she cared about.

If something genuinely comes naturally to you, fantastic. But if it took six tries, three rejections, and an emotional meltdown, that’s cool too. If you’re genuinely fine not having active Friendships, carry on. But if you miss your Friends, pick up the phone—and if one keeps blowing you off, give yourself permission to stop calling. And if you genuinely aren’t looking for a relationship, go on with your cool self. But if you are, that’s also cool.

It’s even cooler if you say it early on.

Intentions are cool. Caring is cool. Effort is so fucking cool.

And the coolest thing you can possibly be is honest.
—Your Friend