I saw that Otin did one of these a while back and I absolutely fell in love with the idea. Only problem was I had trouble figuring out what I would say to myself but I think I've come up with something.
Dear Past Self,
Damn, you're cute.
I know you think you're chubby and you walk around that high school keeping to yourself but you should really let go every once in a while. I hate to break it to you but once you get to college you're gonna make some bad partying decisions and pack on 50lbs. Don't panic! You'll lose most of it but you'll never have that perfect high school curve ever again so skip the tankini and go for the string bikini instead. You will not regret this decision.
When you get to college there will be a lot of choices you'll have to make. I thought about telling you to avoid certain people but then decided against it. Knowing you, you'll over think it and f*** everything up for us. I don't want you to do that. Just go with your gut and don't ever let anyone tell you what to do. You'll be okay.
A Wiser Version of Yourself
Dear Current Self,
Damn, you're cute.
It's been a long road hasn't it? I can't believe we've made it this far and lived to tell the tale (and what a tale it is).
There are a lot of things you're questioning right now. Did you make the right decisions? What if you did that other thing instead? Personally, I don't think all of these "what if"s are going to get us anywhere. This is the way things are, but this isn't the way things will stay forever. We need to keep our head up and keep moving on. You'll be okay.
Your Crazy Self
Dear Future Self,
Damn, I hope you're still cute.
I also hope we have a cute husband, cute kids, cute dog, and cute house. I also hope that I did not depress you due to the fact that you have none of those things. If you don't, then I'm sure there's still time. No one specified just how far in the future you are.
Remember the student teaching dinner when that middle school principal told us that the only way to keep our sanity is to keep doing what we enjoy doing? Follow his directions. Keep doing the writing thing. We enjoy it and it's helped us over the past year.
Maybe you're not young anymore and I know that you're a little sad about that, but we had fun dammit! We had our day and now it is time to pass the torch on to the next generation. Don't be that old person who is still wearing my clothes. They don't look as cute on you as they did on me.
Also, continue to keep your head up. It's gotten us pretty far until now. You'll be okay.
You are okay, right??
A More Foolish Version of Yourself