When I Was Cool: An Illustrated Essay

Something I think all humans do, and have perhaps done since we were living in caves, is that we remember an embarrassing incident we were involved in and wince in psychic pain as we relive it all over again.  Sometimes the memory rears its head right on the cusp of sleep, when we’re at our most comfortable and innocent.  I can imagine our prehistoric ancestors, barely illuminated by a dying fire late at night, snapping their eyes open and feeling existential dread for inadvertently committing some dreaded faux pas.

My painful, embarrassing moment comes from when I was hanging out with some friends of mine at a party.  I was 19 years old, sort of learning how to become an adult on my own.  We were sitting on a carpeted floor upstairs, arranged in a circle, drinking beers, passing around a bottle of whiskey and a bong.  We’d sip from our beers, take slugs from the whiskey, rip the bong, and make each other laugh.

One of my friends asked the question, “When did you realize you were cool?”

And it’s a fair question.  Everyone there was, indeed, super fucking cool.  As their own answer, someone would say something nice and flattering to the group too, like, “I didn’t really ever realize I was cool until you all thought I was,” and everyone would go, “Aww” and blush.  What a cool fucking answer, to make everyone else feel cool instead.

Now, I never, ever considered myself to be a cool person.  I still don’t.  I don’t mean that in a self-deprecatory way.  I don’t dislike myself any more than I feel is healthy to dislike one’s self (I don’t trust anyone who doesn’t self loathe at least a little bit), but I think it’s more than fair to agree that, no, I’m definitely not a cool person.  I’m nice!  I think I’m a nice person!  But cool?  No, thanks.  I’ll leave cool up to the kids.  They can have at it.

So, when it came my turn to tell everyone my story of when I realized I was cool, I decided I was going to wing it.  I’d wung things before, so I was no stranger to the process.  I opened my mind to a sort of stream of consciousness and allowed myself to talk.  I was going to freestyle it and see where it took me.  It… didn’t take me far.  I wanted my stream of consciousness to take me down the river and back, but I only got a few words in and choked.

I remember distinctly that I said, “I realized I was cool when I—” and then panicked, realizing I had nothing to follow after that, but kept going on anyway, and continued “—was walking down the street, and looked at my shoes.”  I immediately became embarrassed, realized that I was never cool, will never be cool, and that I was being so uncool in that moment that I was scaring everyone.  I saw gaped mouths of horror staring back and me and I choked back a single sob, wiped tears from my eyes and stopped talking immediately.

Looked at my shoes?!

Someone else took over and told their own story about positive self-realization and got everyone back on track laughing again, but my night was ruined.  The damage had been done.  When I think back about what happened in real time, what happened was someone asked me when I realized I was cool, and I said, “I realized I was cool when… I was walking down the street and looked at my shoes,” then cried a little bit.  I can’t possibly imagine a less-cool way of answering that question.

On a Coolness Scale, ranked from Fonzie to Urkel, I’d rate my story three scrappybillys.

Bonus Content

This is an idea I had for a long time.  I can’t remember how I came up with it, but I remember explaining, “Because I’m afraid of tarantulas,” whenever I’d detail the idea to someone in these weird, vague terms.  “It’s this guy, who, like, looks like he’s from a comic strip from the 30s, see….”

This one… chickens are just dumb.  If you’ve ever had chickens, you know they’re just… man, they’re dumb.