There were several dares to choose from – here is a list from Tom’s website HERE.
Know that as you get older, you will continue to write letters to your past and future self. And before I write anything else to you, know that you are still true to yourself, and that you are loved.
You’re 16 years old, so that puts you in 11th grade? Oh no, does that mean that you’re still dating him? I guess that’s where I’ll begin this letter then. You won’t understand why he leaves you, but know that it isn’t the reason you think it is. It’ll be so, so hard. I know baby, it’s going to hurt for a long time, but I’m so proud of you for putting that energy into your AP exams and acing them. Especially that 5 in AP Biology you’re going to get – it’ll be worth every tear you shed after he dumped you.
Don’t worry, you’re too young to know it, but it happened for a good reason. It wasn’t a realistic relationship and you both would not have remained satisfied. Especially once you started college. I know you admire Jess and Gideon right now, but not every couple is meant to end up like them. By the way, I’m 21 now, and they’re still together, it’s amazing.
I need to steel you for something. I know that college was mainly about escaping the parent trap, but you’re going to meet some AMAZING people along the way. People you can’t really imagine life without anymore. Cherish your high school friends though, because after HS, I think we both know the ones you’ll keep in touch with.
I’m supposed to detail the journey. I guess I can give things away if you promise not to dwell on them. Maybe if you were able to process this and then forget it, maybe it would make you a confident person? But I know giving you the details now would totally mess up the future. I mean, the ME who is writing this letter doesn’t remember receiving it at 16, so there has to be some way of explaining that. I guess there were moments when a peaceful assuredness came over me. Perhaps that will be the feelings elicited from this letter.
Your journey will be bumpy. Nobody has a smooth journey anyway, and what would be the fun in that? Boring, plain old vanilla.
Your mom still makes the most amazing cold coffee. Aka coffee milkshake. And no, you still don’t have an actual Coffeemaker in your life.
I’m stalling. I need to tell you about college, but that means opening up a raw, still sort of vulnerable part of me. But this letter is being written for an honesty challenge, so I’ll get to it.
You will end up in your dream college! It will be extremely tough, and you will not be an A student. Your 4.0 from High School will pretty much mean nothing.
College will be a lot of firsts. Your first kiss, your first drink, your first time kissing a girl. Your first time completely drunk. Your first time…doing it. Your first boyfriend. Yeah, somewhere along the way, you will realize that Dan didn’t even count. And all that heartache was for nothing, except the 5 you got in AP Bio, like I said, will make it worth it in its own twisted way. Want to know something better? You still talk to him.
You will be stronger, more independent. You will have experienced things, dined out, drank, partied, gone clubbing. WALKS OF SHAME. A few of them. Okay maybe like one.
You will be less of a nerd. You’ll have a life, and you’ll have a wonderful time in the city. You’ll fulfill your dream of living in your own apartment in the city. No guest policy or anything.
No, you still haven’t been to Top of the Rock. You have, however, now been to Coney Island once, and also to the Highline now.
You know what it feels like to reject somebody’s advances. It’s a heady feeling, and you probably understand what Dan and John felt like. You know who I’m talking about. But you’re still sensitive, and you’ll try your best to make amends. It isn’t your fault you’re fabulous, right?
Right now, the almost-21 year old you is at a crossroads. You really want a boyfriend. I really want a boyfriend. I guess in that department, we’re just going to remain lacking. Let’s see how things turn out, shall we. Everything happens for the best.
Boys will always send mixed signals. Just trust your head and study a lot when you feel down. That’s a good habit, keep it. In fact, I love you for it.
Yours always and forever,