Dear Highschool Me,
I Forgive You for Everything You Couldn't Figure Out On Your Own
Dear Highschool Me,
It’s been over a decade since high school. Crazy… I know. I spend many moments of my life now, and when I reflect back, I realize just how long ago highschool was. When I think on those moments, you come back to me. I remember everything you went through, the wins and losses, the good, and the bad. In fact, what I remember most, unfortunately, is the bad.
I remember the texts, the poor decisions, the fights. I remember sticking our feet in our mouths more times than we can count and saying things we would regret. I remember how our actions sometimes ended friendships. Most of all, I remember the sadness. I remember the pain that you felt. That’s why I wrote this letter. I wanted to say, for the first time ever, I forgive you. I forgive you for the texts, the breakups, the mispeaks, and the cringey moments. I forgive you for all the wrong you feel like you did, all of the things you did that made you feel like you were forever tainted, forever unworthy of love or success. I forgive you.
For years I felt like I punished you for what we couldn’t control. I kept pushing down what you felt, what you were trying desperately to bring up. I kept blaming us, blaming you for some moral failing on your part that made us fail, something that kept us from living up to our potential. I am sorry that I punished you for your cries for help. Looking back now, I know that you were doing the best you could with the tools you had, which weren’t the best tools for the job. The bike accident, the abusive girlfriend, the bullying, and your own insecurities left your tools incomplete and not the most effective. This whole time, all the flashbacks and the memories were cries for help, cries for closure that I had ignored, because I felt like it was our fault that we didn’t do better. I’m sorry I wasn’t there for you. You tried your best, and I forgive you for where we fell short of the mark.
I want you to know that life is better now. We don’t have the perfect body we always wanted, and we’re not a millionaire (yet), but what we have now is incredible. We have a wife who loves us, a good job, and our relationship with our dad is healthier than ever. Not to mention, we have a fun and slowly growing corner of the internet that reads what we write. We have a bright future ahead of us, and we’re worthy of it, every last bit.
Sincerely,
Your friend, you.
This week I had a powerful experience that is causing me to do something that I don’t think I’ve ever done in my life: I am writing a letter to forgive my high school self.
It sounds strange, but I was talking with an AI model about my mental health (I know…you're not supposed to do that) and about how to integrate my inner shadow. While we were talking, I started to spill my soul deeper than I ever had before (except maybe to my wife). I tried to lay everything that was disturbing my peace bare out in the open, leaving nothing hidden.
The response I got was something I didn’t expect; it wasn’t a bland platitude or “it’s okay to not be okay” kind of comment; instead, it was actionable. The AI took what I was feeling and came to a conclusion that resonated with me, and it told me some things I could do to help me. What you just read was one of those things. For the first time in my life, I forgave my highschool self.
I’ve been stewing on that regret for over a decade now… It feels good to let it out. I didn’t write this to get your pity… honestly, I wasn’t planning on putting this here at all. But as I thought about it last night, I felt like sharing it just might help somebody else.

