I was twenty-three, standing in an art gallery, holding a glass of wine I did not want, looking at a painting I did not understand.

The painting was a large canvas covered in what appeared to be random splashes of red and black. There was no shape I could recognize, no image I could name. My honest reaction was simple: what is this? But I did not say that. Instead, I turned to the woman beside me and said, “Fascinating deconstruction of capitalist imagery.”

I have no idea what those words meant. I had heard someone else say something similar earlier. It sounded intelligent. It sounded like something a person who understood art would say. So I borrowed it, wore it like a costume, and waited for approval.

The woman nodded. “Absolutely,” she said. “The tension between form and void is remarkable.”

We stood there, two frauds admiring each other’s performances, neither of us willing to admit we had no idea what we were looking at.

I think about that night often. Not because it was unusual, but because it was so ordinary. I had been performing my entire adult life. Pretending to like music I found boring. Pretending to enjoy books I never finished. Pretending to have opinions I had simply copied from people who seemed cooler than me.

Cool. That word. That expensive, exhausting, fraudulent word.

What is coolness? I have thought about this for twenty years. The best definition I have found is this: coolness is the performance of not caring. Cool people do not get excited. They do not show enthusiasm. They do not admit ignorance or confusion. They maintain a careful distance from everything, as if genuine engagement would be beneath them.

I spent years trying to be cool. I learned to hide my excitement when I liked something. I learned to pretend familiarity with things I had never heard of. I learned the strategic smirk, the knowing nod, the casual dismissal of anything too popular or too sincere.

It was exhausting. And it was lonely.

Because coolness is a wall. It keeps others out. When you perform indifference, you cannot connect. Connection requires vulnerability—admitting you don’t know, showing you care, risking the embarrassment of genuine enthusiasm. Cool people do not risk these things. They stay safe behind their masks. And they stay alone.

I remember the moment I began to see through the performance.

I was at a party, surrounded by cool people. Everyone was performing. Strategic laughter at jokes that weren’t funny. Careful opinions designed to impress rather than express. References dropped like credentials. I looked around and realized: everyone here is terrified. Everyone is pretending. No one is actually having a good time.

Then I noticed a man in the corner. He was older, maybe fifty. He was talking to a young woman about something—I couldn’t hear what—but he was animated. His hands moved. His face changed. He laughed loudly at his own joke. He was completely uncool. And the young woman was captivated. She was leaning in, engaged, genuinely interested.

He was real. Everyone else was performing. And she could tell the difference.

That night I started to understand something. Cool is a moving target. What was cool when I was twenty-three is embarrassing now. The music, the clothes, the attitudes—all of it dated, all of it cringe-worthy in retrospect. I had contorted myself to fit a standard that would change before I could even master it.

But the man at the party—his realness would never go out of style. Authenticity does not age. Enthusiasm does not become embarrassing. Genuine curiosity, honest confusion, unguarded joy—these are timeless because they are human.

I started experimenting with honesty. Small experiments at first. When someone mentioned a book I hadn’t read, I said, “I haven’t read that. Is it good?” When I didn’t understand something, I asked questions instead of nodding along. When I liked something uncool, I admitted it without apology.

The results surprised me. People did not think less of me. They seemed relieved. As if my honesty gave them permission to be honest too. Conversations became real. Connections formed. The wall of coolness came down, and suddenly there were people on the other side.

I am forty-five now. I have stopped performing almost entirely. I admit when I don’t know things, which is often. I show excitement when I’m excited, which embarrasses my teenage daughter. I ask basic questions that reveal my ignorance, and I no longer care who notices.

This is not courage. This is exhaustion. I simply do not have the energy to perform anymore. The cost of coolness became higher than the benefit.

But something else happened too. I started to like myself more. The performed version of me was always slightly wrong—a costume that never quite fit. The real version, with all his enthusiasms and ignorances and unfashionable opinions, turns out to be more comfortable to inhabit.

My daughter thinks I am embarrassing. She is probably right. I get excited about things she finds boring. I ask questions she thinks I should already know the answers to. I laugh too loudly and care too visibly and fail entirely at the indifference she is working so hard to master.

But I notice something. When she is upset, she comes to me. Not to the cool parent, but to the embarrassing one. Because she knows I will actually feel something with her. She knows I will not perform concern—I will be concerned. The uncoolness she mocks is also the authenticity she trusts.

Perhaps this is the trade-off. Cool people are admired from a distance. Real people are loved up close. Cool people impress. Real people connect. You can have one or the other. You cannot have both.

I think about that art gallery sometimes. I wonder what would have happened if I had told the truth. If I had looked at that painting and said, “I don’t understand this at all. Can you help me see what you see?”

Maybe the woman would have thought I was stupid. Maybe she would have walked away. But maybe—and I think this is more likely—she would have been relieved. Maybe she would have said, “Actually, I don’t really understand it either.” Maybe we would have laughed about it. Maybe we would have had a real conversation instead of a performance.

I will never know. I chose coolness that night. I chose the mask over my face.

I don’t choose it anymore.

My weirdness is my signature now. My ignorance is my invitation for others to teach me. My enthusiasm is my gift to people who are tired of strategic indifference.

Cool is a mask. Real is a face.

I spent too many years wearing the mask.

It is good to finally feel the air on my skin.