For most of my life, I’ve been a Cool Kid. Now before you jump all over me, calling me a prick and what have you, please note the capital C and K. I’m not talking about adjectives, I’m talking about proper nouns: a category and designation all its own.

Starting in about 1991, I fell in with the people who set the social tones at recess and elsewhere. Every Cool Kid had his or her place. At Hamilton Elementary, we had such standards as Fastest Boy or Girl, Kid Who Kicked The Farthest In Kickball, Kid Who Can Actually Draw … the list goes on. For the record, I was Tall Black Kid Who Did Not Intentionally Terrify White Students (let’s be real — I’m still that).

While the selection process into the fold was extremely arbitrary, there were a few things that could nudge said process along, including cool clothes, cool sneakers (Sidebar 1: When Brett Cowman busted out the black-and-white Bo Jacksons after Christmas break in second grade, his stock skyrocketed), athletic deftness during gym class or — and this is truly clutch if you can swing it — an older sibling that is a Cool Kid.

It’s not to say that Cool Kids didn’t interact with other kids, it’s that such fraternizing needed qualification, i.e. So-and-So is funny and a rather fearless dodgeball player. In fact, there were always a handful of kids who ascended to the Cool Kid ranks for such feats of courage. It was something like Social Scene Affirmative Action. Still, in an unstable atmosphere, theirs were the most precarious positions of all. In a “what cool thing have you done for me lately?” sort of world, it was swim coolly or sink quickly.

In middle school, the dynamics were essentially the same, though the categories changed somewhat. There was the addition of such wrinkles as: Basketball Team, Baseball Team, Cutest Guy, Cutest Girl and the oft-pursued Cute Girl With Boobs. The system was scarily efficient. At Wickford Middle, which housed the students of two elementary schools, the Cool Kids found each other and took our rightful place at the top. I think we legitimately liked each other, but I also think we inherently knew we were supposed to like each other. For us, whether we were cool or not was not a matter of contention. We were the defenders of the Cool Canon because life up to that point had said so.

Because Cool as a social order is nothing if not consistent, high school was much of the same with drugs, booze and sex thrown into the mix. In a general sense, going to prep school is not considered cool, and being a Cool Kid at prep school is like coming in seventh in the Olympics. While it is an accomplishment, the rest of the world doesn’t consider it that great. It wasn’t until I got to prep school that I became thankful for being considered Cool in the conventional public-school sense despite the fact that, in many ways, I was a nerd. Moreover, I saw that there were different kinds of Cool in all kinds of people. It wasn’t conventional Cool Kid cool — I mean, prep-school kids are nutty — but it was something I could recognize. Still, it took me four more years to truly realize which Cool actually mattered.

I wish I could say something like, “And after prep school, I was completely changed and always managed to find the best in all people,” but I can’t. Though life has taught me not to be too gassed on myself by roughing me up a few times, I still have moments when I’ll look around Yale and think that I’m surrounded by lames. The difference between saying that now and saying it previously is this: Cool Kids are not exempt.

Cool is more complex than I used to think. I certainly think that Cool Kid coolness in college matters a lot less than it does in grade school for the simple fact that there are too many people and too many subsets to contend with. That is not to say there are no Cool Kids, or rather people that are convinced of their Coolness, it’s just that they are merely a group of people that exists rather than a social juggernaut that sets the tone for everyone else. In fact, it’s probably more accurate to say that each subset has their own Cool Kids and they set the tone for whichever particular group they inhabit.

Yet, in all my understandings of Cool — at least in what I think I understand — it wasn’t until I was 21 years old that I finally recognized the difference between Cool Kids and Kids Who Are Cool. Kids Who Are Cool are not cool in the Cool Kid sense. It is unlikely that they set the social tone of any environment they are in. Their attributes often go unrecognized in the social marketplace, but what they excel at is one of the few things in life that actually matters: friendship.

Cool Kids are not good friends, not because they are terrible people, but in fact because they are, oftentimes, well-liked and have a charisma that people are attracted to. The demands of the social market require that Cool Kids sate the appetite of the public. While it is rarely said, it is understood that there is no time for friends when the masses call. For Kids That Are Cool, the obligation is different. Their loyalty lies in their friends. For Kids That Are Cool, being considered a Cool Kid is essentially worthless.

True Story: Senior Week 2006, a friend called me to meet up before she left. When I got to her room, I saw about 15 people sitting in a circle with a table of booze in the middle. I didn’t know most of the people in the room, so I had no reason to stay for more than a few minutes, but instead I sat down a little outside the circle and just took it all in. For the better part of an hour, I watched people pass a deflated football around the circle and tell stories about one another. Surely the relationships between all of those involved are more nuanced than this snapshot, but as I sat there and watched people cry over the end of an era, I couldn’t help but review my own life and the people I generally kept my counsel with. For all the Cool Kids I knew, for all the Somebodies that I was acquainted with, I couldn’t help but feel jealous of this group of people I was given the opportunity to observe, people generally anonymous by conventional Cool standards — jealous because, at the end of things, they were cool enough to remember who and what mattered.

Funny, in all this talk about Cool, I haven’t defined what Cool actually is. Honestly, I can say I don’t know. But neither do Cool Kids. Peace to entryway B.

Penultimate Thought: I now understand the hype about “24.”

Final Thought: White Southerners: Black people with rights.

Jon Pitts-Wiley is that bully you knew back in elementary school. Don’t let him tell you any differently. Sure, he might say that he was “just” a Cool Kid but we all know the truth Mr. Pitts-Wiley, don’t try to run from the past.