Introduction: Coolness, That Endangered Species
Let’s be honest. “Cool” is one of those words that dies a little more every time someone earnestly uses it. It was murdered first by dads in cargo shorts, then resurrected ironically by hipsters, and finally embalmed by corporate branding teams who thought tweeting “How do you do, fellow kids?” would make Pepsi edgy.
Yet, despite the tragic decline, people still crave it. Being cool is like getting into an exclusive nightclub with no line, no cover charge, and free drinks forever. But here’s the thing: the harder you try to get in, the more the bouncer knows you don’t belong. That’s the paradox of cool—you can’t fake it, but you also can’t really earn it. It’s like charisma mixed with witchcraft.
So, welcome to this “short course” on coolness. It’s not short, and it won’t actually help you. But if you want to waste 15 minutes of your life learning how to stop embarrassing yourself at parties, buckle up.
Lesson 1: Stop Announcing That You’re Cool
The first rule of Cool Club? Don’t talk about Cool Club. If you say, “I’m cool,” congratulations—you’ve just outed yourself as the human equivalent of a participation trophy.
Coolness is a vibe. It’s the difference between James Dean leaning against a wall with a cigarette and your uncle leaning against a barbecue grill asking if TikTok is still a thing. One looks effortless. The other looks like a public service announcement about midlife crises.
The true giveaway? Language. Cool people don’t say “cool” unless they’re mocking it. They also don’t use “vibes” unironically past age 27, and they definitely don’t send you memes three weeks late with the caption “This is so me.”
Lesson 2: Master the Art of Not Caring (But Secretly Caring A Lot)
The performance of not caring is cool. The actual state of not caring is just apathy. Apathy smells like Axe body spray, unopened mail, and regret.
Real coolness comes from selective indifference. You don’t care about the small stuff (who unfollowed you, whether pineapple belongs on pizza, if your socks match), but you care deeply about the right big things. Like art. Or justice. Or which vintage band tee to wear that signals “I was into them before they sold out.”
It’s the delicate balance of shrugging when someone insults you, while also spending three hours in the mirror perfecting your “effortless” hair.
Lesson 3: Develop an Aesthetic
Cool people have a look. They don’t just buy clothes; they curate an identity. They’re not wearing a jacket—they’re wearing a jacket that “says something.” Usually, it says, “I don’t shop at malls, peasant.”
But beware: aesthetic is not the same as cosplay. Dressing head-to-toe in biker gear when you’ve never been on a motorcycle doesn’t make you cool—it makes you look like you wandered out of a bad Halloween party.
A true cool aesthetic comes from consistency. Steve Jobs wore black turtlenecks. Prince wore purple. Meanwhile, you wear Old Navy clearance rack mixed with desperation. That’s not an aesthetic—that’s laundry day.
Lesson 4: Learn the Dark Arts of Timing
Coolness lives in the pause. The delayed text back. The glance that lingers just long enough. The Instagram post that somehow looks casual, even though they took 174 versions.
Timing separates the cool from the cringe. Cool people know when to leave a party (before someone breaks out Cards Against Humanity). They know when to drop a one-liner (never in a group chat full of dads). They know when to disappear entirely, creating an aura of mystery.
Meanwhile, you’re still explaining your joke from five minutes ago, killing whatever ghost of coolness you had.
Lesson 5: Curate Your Cultural References
Coolness is about taste, and taste is about pretending you discovered everything three years before the masses. Did you actually know that obscure Icelandic shoegaze band before they blew up? No. But can you convincingly pretend you did? That’s the skill.
Cool people name-drop in ways that make you feel insecure about your Spotify history. They’ll casually say, “Yeah, I was into them back when they only had, like, 500 listeners,” as if they weren’t also frantically Shazaming the band in a coffee shop.
Here’s the secret: the cool person didn’t discover it either. They just lie better.
Lesson 6: The Social Jiu-Jitsu of Coolness
Cool people aren’t loud. They don’t dominate conversations. They don’t need to. They weaponize silence, smirks, and well-timed exits.
Think of coolness as social jiu-jitsu. While everyone else is flailing, trying to be noticed, cool people lean back, sip their overpriced drink, and let the attention come to them. Their power move is acting like they don’t need the room to like them—even though they absolutely do.
The rest of us? We’re human golden retrievers, desperate for approval, panting and wagging our tails for scraps of validation.
Lesson 7: Pick the Right Vice
No one ever became cool by drinking a sensible amount of water and getting eight hours of sleep. Cool people always have a vice—something that makes them look rebellious, dangerous, or at least Instagram-worthy.
It used to be cigarettes. Then it was artisanal whiskey. Now it’s probably microdosing psilocybin while lecturing you about cryptocurrency. The trick is to have a vice that looks edgy but won’t completely ruin your life.
Cool = mysterious. Not cool = losing custody hearings because you thought meth was a vibe.
Lesson 8: Don’t Try Too Hard (Which Is Impossible, Because You Already Are)
The central irony of coolness: the minute you consciously pursue it, you’ve lost it. It’s like chasing butterflies—you end up sweaty, weird, and empty-handed.
Cool is walking into a room like you belong there. Not cool is walking into a room like you’ve rehearsed this entrance in the mirror 47 times. Cool is wearing sunglasses indoors because you forgot they were on. Not cool is wearing them indoors because you thought it would make you look like Johnny Depp.
The second you read an article titled “How to Be Cool,” you’re already doomed. Which, unfortunately, brings us to you.
Lesson 9: Accept That Coolness Ages Like Milk
Even the coolest people eventually lose it. The once-cool band guy is now a middle-aged man yelling about vinyl purity. The indie film darling is now doing Netflix rom-coms. The skater kid with perfect hair is now bald with a bad knee.
Coolness expires. Confidence doesn’t. If you can transition from “effortlessly cool” to “confidently uncool,” you might just survive adulthood with dignity intact.
Otherwise, you’re the 45-year-old still talking about how high school was your peak. Yikes.
Conclusion: The Final Exam
Here’s the final exam for this course: Go to a mirror. Look yourself in the eye. Now ask, “Am I cool?” If you actually have to ask, the answer is no. But don’t worry—most of humanity isn’t cool. That’s what makes the rare few who are seem so mythical.
Coolness is a rigged game you’ll never win. So the real hack is to stop playing. Lean into your weirdness. Own your quirks. Be the person who laughs too loud, wears socks with sandals, or still thinks puns are funny. Because authenticity may not be cool—but it’s the next best thing.
And honestly, nothing is cooler than someone who doesn’t give a damn about being cool.