My Life in Shame – Episode 2 – The Middle School Years


In part 2 of this epic saga of my most regretted moments, I cover the start of The Awkward Years. This is the time when boys begin to dream of being older. They’re old enough and just mature enough to see what the big kids are like and what they’re up and to want to emulate it. This is to say they’re dangerous—little a-holes in the making. More often than not this emulation involves pretending to be cavalier and independent to a degree that is not felt internally in the least. You see kids in the throes of this stage all the time. Anytime you are out somewhere and you see pre-teen or early teenage kids running around, flailing arms, making noise and generally calling attention to themselves in a way that can really only be described as “unfortunate”, you are witnessing kids trying very hard to impress upon you that they, for the record, do not care in the slightest what you think of them. This is tricky because being able to effectively communicate this depends desperately on your paying attention to them.

Thusly, I am sufficiently introduced.

I was part of a pretty tight cadre of boys. We had all been at school for a good long time, some of us since first grade. We’d have sleepovers and were intensely into the gateway elements of “cult culture”. Not the rock band, not Scientology. Real Genius. Monty Python. Mel Brooks. Army of Darkness. We had our in-jokes and our one-liners that we’d throw around.

We also had a real sense of competition between us. If you’ve ever played a video game that only seems to have the high score list to measure success and thought to yourself “That’s it? That’s all the incentive to play is?” you have not hung around enough 13-year-old boys (note: seeking out 13-year-old boys to hang out with might lead to some awkward encounters). To ride atop a high score list, to be able to point to something very real and have it be known to all that you are the most awesome at killing people in Goldeneye with proximity mines is to be king. You’re all buddies and you’ll cheer your friend with all your heart when he’s riding on top of the world but the fire burns strong to knock his punk ass off the top of that heap so you can reap the glory you so richly deserve.

Most of the time when kids get into trouble it’s less because they had the idea to do something bad on their own and more that they wanted to prove that something that is an exceedingly poor idea could be accomplished, or they just wanted to prove that “Pffft. Yeah, I’ll do that.” The best way to not have to be the one stuck doing things is to be the one daring the others to do things.

The particular dare in question here took place at Magic Mountain up in Valencia before it added Gang Shankings to its list of featured attractions. We were leaving the park; I was probably only a few hundred yards from avoiding permanent embarrassment. Me and the other young Lotharios I was with had somehow gotten it into our heads that the truest test of our awesomeness on this day would be to approach some attractive young lady and ask her for a kiss. She would, of course, be overwhelmed at our boldness and readily apparent maturity, and consent.

This was a dare that had been tossed out and no one had picked it up. So, as we were leaving the park, it began to get shuffled about around the group like a hot potato. The longer it went before someone claimed it, the greater the subsequent glory would be. It clearly crossed an invisible threshold for me after a time, though, because I seized upon it. “Yeah, I’ll do it.” (Incidentally, this unknowable threshold to simply “man up” and do something unexpected is also the source of one of my proudest high school moments. How you doin’, Lauren Sherman?)

There was a girl walking with a friend and, in all likelihood, some other form of chaperon that I blissfully didn’t take any notice of in the slightest. I approached, excused myself as an means of introduction and began my spiel.

“Excuse me. Hi.”

At this point, both she and her friend look wary but interested. Potentially this will be something funny or interesting. They are not wrong from a perspective that is not my own.

“My friends over there have dared me to come over here and…”

If there was ever any moment that you may have thought that a young kid ever had the chance of really being smooth, just refer back to that clause. This seemed to be an acceptable thing to me. “Those guys over there told me to do this.” Really, anything else that popped out of my mouth after that is going to be a sort of insult. I don’t care if I wrote a sonnet on the spot. I didn’t do it because I wanted to do it. I did it because those guys over there told me I could not do it. Is there a better aphrodisiac than spite?

“… tell you that you are very pretty…”

It’s at this point that her face brightens up and she blushes a bit. Her friend even grins because she’s happy for her. It’s a compliment! They’ve missed the insulting introduction about the compliment being the result of a pressured dare! She’s pleased! I am GOLDEN.

“… and ask you for a kiss.”

Her faces crashes into a look of revulsion that burns itself indelibly into my mind (see Exhibit A: This Post). I shrug and turn around immediately—cavalier—and return to my friends. I am, quite clearly, the man. They are laughing and clapping me on the back and talking about how they can’t believe I did it. I am as much a celebrity as I am likely ever to be at that moment.

I am also totally horrified. The notion that I could do something that would cause someone to make that face remains absolutely haunting to me.

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