The Kiss Bet: Oliver & Sara Oneshots

Dear Oliver

Dear Oliver,

     If you're reading this, then you've probably admitted that you like me in some way or another, and I feel the same! Of course, you probably knew that much already considering present-day me most likely already said that before sending this, but the interesting part about this note is that I'm writing this back in May of my senior year and your junior year. But honestly, when I'm writing this, I don't think you like me back... Well, why am I writing this, then? I don't know, maybe it's dumb, but I guess the simplest answer is out of hope.

     I always knew somewhere in my heart that someday, if things were truly meant to work out, you would finally notice me and start thinking of me in that way, and see what I have to offer exactly as I am, because I never wanted to change who I am for someone, even including you despite everything I've felt for you, so I always knew that if you ever fell for me then it would be because you liked me for who I really am. I suppose it wasn't so much that I KNOW things will come around for us, but more so that deep down there's just this small little bit of hope that maybe, just possibly, someday you could feel the same if things are really meant to happen between us. That was kinda what kept me going for the longest time, and still is when I'm writing this; feeding off those tiny little pieces of hope to keep myself from being too sad over the unrequited feelings until I found myself ready to move on. Clearly, if you're reading this, that day never came, and I am so so grateful that it didn't, because if you're reading this, then I assure you that this is all I've wanted for the longest time, and even on the bad days when it hurt the most or seemed like things would never change, I never let myself give up hoping. This is the day that makes everything from the last bunch of months (who knows, maybe years by the time you're reading this) worth it, all the waiting and all the hope that I thought may be pointless for anything other than keeping my chin up, because there was a small part of me that never let go of the hope that things would eventually work out how they were supposed to for us.

     I always sort of took it as my sign that if I was open to allowing myself to move on while stepping back and not acting on anything so I didn't push any boundaries if you didn't feel the same, but just couldn't truly move on, then maybe there was a reason I wasn't meant to move on just yet. I hope the fact that my past self, possibly from quite a long time ago by the time you see this, is telling you that I've never given up and always tried to keep moving forward is enough to show you just how important this is to me, and how much it means that you've grown to feel the same, even if it may have taken some time. I won't lie, I'm initially writing this with a bit of a heavy heart in fear that I'll never get to send you this letter, but maybe someday things will change, and if you're seeing this, then they have and I promise, my present self couldn't be happier that things have changed like this, and if you don't believe it, then go ask present-day me who showed you this letter yourself. I hope you get to see this someday.

- Past Sara :)

The girl sighed. Would she ever get to send this? Probably not... But the possibility made her smile nonetheless, even if she saw it as a rather unreliable and unlikely possibility.

Maybe it hadn't been such a bad idea after all, she decided; writing a letter to future Oliver, expressing all her present feelings to show him that hers had been long-ongoing if he were to ever confess his own. Not that she expected him to, though. He didn't particularly seem to want to be much more than just her grumpy tutor who clearly had an intense aversion to romance and her boy problems, especially the idea of teenage dating.

Even if she thought he'd never feel the same, though, at least writing a letter for such a situation was enough to give her a chance to lay out the hope that she had remaining, and make the chance of the feelings being mutual feel more real. Almost like a preparation for something that'd be happening someday, a preparation for a reality so that she could properly articulate things here if she were too flustered or frazzled at the moment in the real world.

Once she felt satisfied with her revisions, she returned her finger to the trackpad of her laptop, clicking into the title of the document and typing to change it. Rather ambiguous, she'd say, but such a title was just enough for her to know exactly what it was, should she ever need to send it.

"Dear Oliver"

A/N

Hey y'all!
Can you take a wild guess what I'm gonna say here? Surprise surprise, it's inspired by real life lol- I've written a letter like this for the guy I like, and I thought the idea of Sara making something like this felt very sweet and wholesome, like she was using it as some sort of coping mechanism for what I can imagine her actual reaction would be in canon to realizing she likes him. Y'know, thinking it's unrequited, thinking he's totally uninterested, the whole shabang.

I didn't want to include this because it felt incredibly pessimistic, but I'm terrified that my situation will someday take a satrick turn, and only after I've moved on will he finally like me, so I've made a second version of my letter too, which just feels like an interesting thing to share with y'all lol. The titles are less ambiguous for the sake of differentiating the two, so it's "Dear Julien: A Letter for if Someday You Feel the Same" and then there's "Dear Julien: A Letter for if Someday You Like Me, but I've Moved On" but obviously we can't use that here when Olivara's gotta get together in the end hehe- ok but side note, i literally do not know anyone named "Julien" which for some reason is really funny to me LOL bc it's a code name that only I understand since it's a reference to something but it's hilarious that i'm using a name that i know literally no one by for someone that i'm legit in love with pfffff-

Anyway, I hope y'all liked this story, please leave any ideas, prompts, thoughts, or constructive criticism in the comments, I love seeing your feedback!!