A Letter To My Future Self

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During my junior year of high school, I sat with a few guys at lunch, one of whom was a senior. He was a good guy, more on the shy and quiet side, which was the complete opposite of the other guy I sat with who was loud and overly flirty. I wasn’t as shy back in those days and I was still pretty open with my friends about things, so we all got along interestingly well despite our differences.

As the year came to an end, he and I decided that we were going to write “goodbye” letters to one other. On the last day of school, he handed me his letter and instructed me to wait until I got home to read it. The letter was neatly folded (because who didn’t fold their notes into cool shapes back then?!) and he even drew my name on the front in colored pens, which showed me that he really put some thought into it.

I opened his letter, and this is what it said.

You want to know what will happen someday?

Someday you will be sick and tired of being afraid of dating again. After all you don’t know what type of asshole you may have on your hands once you get to know him, but your search for someone has matured on this later day.

The guy you’re watching doesn’t put his arm around you, doesn’t poke and tease you (well, maybe a bit), he won’t try to put the moves on you, he’s a bit shy and awkward with words when around you, but most importantly he is interested in what you think and listens to what you say.

He’s not a partier and not much of a dancer. He’ll like shopping and enjoys all movies and types of music. Chances are that he will be exactly what you were looking for all along but never knew you wanted it. You’ll have a hard time finding him, mind you, because he’s just as afraid to date as you are. He’ll avoid you because in order to go on dates you’ve got to have “cool” things, and he probably won’t have much to brag about. He’ll mainly be afraid to date because he doesn’t know if you will be a bitch once he really gets to know you.The right guy will be as frightened to find you, as you are to find him. Just keeps your eyes and your heart open. I guarantee you’ll have your share of bumps and bruises on your search, but how else will you find out what type of guy you don’t want to date?

Reading this letter again many years later, I can’t help but wonder about what he wrote. I have a general idea of what kind of person I want to date, but what if I’m completely wrong? What if the person I’m meant to find is the complete opposite of me? What if we’ve already met, but I’ve written him off because he doesn’t like dancing or clubs or bars or going out or the occasional trip to the trashier part of Indiana for a night at the strip club?

So many “what ifs”…. so many questions and not enough answers.

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Co-founder, Editor. My dating life can best be described as a lazy Sunday afternoon of window shopping.

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