I wasn’t going to write a post tonight, as I spent a large chunk of time going through some of my old junk looking for some test scores from a few years back (I’m trying to settle a bet with a co-worker on who scored higher on a particular standardized test). In doing so, I ran across some stuff from high school I had written, and it is all beyond horrific. So, in order to make sure I can never show my face in public again, I thought I’d share a letter I wrote to a girl that broke up with me after my junior year of high school (a long, long, long time ago).

Let me set the scene: I was set up with this girl by a mutual friend, and we went out for about a month. Little did I know, she was actually sticking around to get closer to my friend Dave, with whom we double dated on occasion. Finally, she broke it to me (after I spent a ton of cash for us to go to prom), and I reacted in true 16 year old fashion, thinking my life was over. So I wrote this letter to her, that I thankfully never sent. Take note of the masterful use of the sports metaphor.


Ever since I began playing sports years ago, people have always praised me for how hard I played and, if I happened to lose, what a good sport I was. I’ve lost.

However, this can’t simply be compared to a crummy game. In sports, you just pick yourself up, regroup, and give it your best try the next time out. But in my situation, I’ve lost a lot more. I’ve lost you, as well as a part of myself. Just like I needed my brain to think or my lungs to breathe, I needed you. The day you leave, it will probably have been months since you talked to me, and you will have forgotten this whole relationship totally. That day will be the saddest of my life (editor’s note – it wasn’t.)

I know you don’t like me to talk that way, but it’s true. That’s the only way I can truly express the way I feel about you. I would list all the great things about you, but my limited vocabulary just wouldn’t do you justice. From the first time we went out, you took hold of my thoughts for good. Every dream and aspiration I had from that point on was in your hands. I made the foolish mistake of falling in love with you, so now I can’t get them back. Whether you want to or not, you’ll always have my thoughts.

Anyway, I set myself up for this, so now I just have to eat it. Regardless of what I think of myself, I always thought I could enhance your life and make it even more wonderful than it was before. I guess we’ll never find out. It’s too bad you let your attraction to Dave get in the way. It blinded you to the fact that Dave doesn’t love you and I do (and always will). (Editor’s note – I don’t). I would do things for you that Dave never could. From this point on, my friendship with Dave will deteriorate quickly (Editor’s note – it didn’t: he was one of my groomsmen a decade later). I wish it wouldn’t be like that, but I know it will.

I’m not mad at you for not feeling the same way about me as I do about you. If not liking me was a crime, the entire female gender would be in prison. It’s a good thing you told me about all the guys who you’ve chosen to not talk to for months at a time, now that I’ve fallen into that category.

I didn’t lay a finger on you any time we went out. (Editor’s note: My ability to take hints wasn’t very sharp at age 16.) That doesn’t mean much, just that I liked you for who you had inside, not just because of your extraordinary beauty.

Well, this letter’s getting too long. Don’t even this begins to sum up everything I feel. You can pass this off as musty garbage, or you can look at the words for what they really mean. Anyway, I realize I’ve lost. In the future, when you’ve totally forgotten about me, I hope you find someone else who loves you half as much as I do. Then you’ll be a happy woman for a very long time.

P.S. – Stay away from the sharp cheddar cheese.

So there you have it – the ramblings of a 16 year old madman. I admit, I was cringing in pain while typing it out. So it only makes sense to share it with the world, right? I figure everyone has times like that during their high school years, I just can’t believe I wrote it out and saved it.

I actually never drank a single drop of alcohol in high school. In retrospect, I should have.

I am now going to puke my guts out.