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On the first day of high school, in my freshman English class, I was asked to write a letter to myself to be read at a future date. Many of my peers chose to read it when we graduated from high school. To me, this scope was limited. I had only aged 3.5 years.

Why not read the letter when I gained twice of life’s wisdom?

That’s why I read mine when I was 30 years old—when I’d be “Mayor, married to a hot girl, play pool basketball in my enormous pool everyday, and live on the same block as Reed and Andrew.” My reaction was strong. The 15 year old letter to self is { poorly structured, ill-conceived, and dangerously untenable } .

man writing letter

Here is my rebuttal:

“Hey dude, what’s up?” Your letter is off to a precarious start with it’s first four words. It gets worse.

“I hope you’re still playing video games.” While you could have left it at that (because I have a swift answer), you didn’t, piling on further “advice.”

“Don’t throw away your XBOX, ever. Remember what happened when you threw away your N64? You regretted it and now Mario Party is cool again.” Not only does the first topic lack technological foresight as to how gaming systems will develop, its merit as a social activity is valueless. I’d reply by saying the numbed-down relaxation you get from FIFA will soon be replaced by images social media algorithms feed you and bourbon you feed yourself.

Then, without any hint of a transition, your letter dives into this question: “Do you still spend the night with your friends?” How naïve.

“Spending the night is the funnest. Never stop.” One, your “friends” all live in different cities. Yeah, that’s what happens after college. And two, some of them voted for Donald Trump. Now, when you see those boys you used to play Halo with, it’s for a lunch when they’re in town on a business trip. You’re probably asking, “Who is Donald Trump?” He’s the weird guy from The Apprentice commercials you see when you’re watching The Office on Thursday nights. He becomes the President of the United States of America. And it’s largely due to the willful ignorance of social bubbles, like the prep school you’re “so nervous about” right now. We’ll get to that later. (The Office is still funny, but a lot of its jokes are problematic).

“Do you still play driveway ball with Reed?” No, you do not. Reed’s wife won’t let us. Instead, she asks him to do other stuff like take care of their kids and earn a living.

“Are you gonna make varsity?” Who cares? Telling people you played lacrosse in high school is essentially starting off a conversation with, “Hi, I’m a douchebag.”

“Does Katherine like you back?” What’s with all the questions? Your letter lacks argumentative structure. Also, no.

“I am so nervous about high school. I can already feel our friend group drifting apart. Cool, older people are asking the girls on dates. And my friends on the football team are starting to drink. I wish we could return to the good old days of swimming in Stu’s pool and watching Nick at Nite.” Finally, a little bit of vulnerability. However, its expectations are misguided.

One, transitions destroy relationships. Period. You’ll get used to it. Two, wishing it were like the past will never help you. It’s a cyclical pattern of self-defeat that prevents you from living in the moment. And living in the moment is what life’s all about it. Last night was a great example. I signed off work at 8:45 P.M., poured myself a steep and stinky glass of bourbon, and stared at the wall, grateful to be living in a brief moment in which I am not working.

Also, I’d like to put something into context for you.

The high school you’re so nervous about is a toxic social bubble, designed to keep its members isolated and feeling self-important.

Instead of being nervous about drinking at parties, why don’t you ask the administration when the school actually “integrated” (use air quotes) and why race and their practiced exclusion aren’t a part of its self-written narrative? That’d be a better use of your time.

“I know by now you’re probably married (who is she, is it Katherine?) and plotting your campaign for higher office. I just want to say best of luck.” Oh boy. This is where your letter becomes dangerously untenable. Marriage is a social construct. You are self-partnered and fine with that. It’s fine that all your friends are married, that Reed and Andrew can’t go on trips because they vacation with their families, that dating apps are really just vapid Yelp reviews of somebody’s looks.

Your assumption is ludicrous, but 15 years later, you’re fine.

And running for office? My lord. Step aside and let somebody of color shape this country. You’re a fucking copywriter.

“Do I lose my v-card before prom?” Why is there another question after the previous paragraph? Also, no.

You then sign off:

“Never stop making people laugh,

The Doodyman.”

I have sad news for you. Not only is this letter way too short, but laughter is not that important. Eighty-five percent of your social interactions are with your coworkers, and nobody is hired because of a shared sense of humor.

I’d like to end with a few notes of advice. Gain some structure in your prose, skip the poetry electives you’re gonna take in college in favor of some coding classes, and stop calling yourself “The Doodyman.” It prevents people from taking you seriously.


P.S. – Mom and Dad get divorced.

Robin Doody

Thinks of himself as the love-child of Tim Riggins and Max Fischer.

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