Friday, October 19, 2012

Dare: Natalie Whipple + High School Crush + Letter

This dare was sent a long time ago by Elodie, and I thought it was time to bring it out to the light. She dared one of us to "write a letter to our high school crush." Oh yes, here goes nothing. You are about to get a lovely window into my teen angst.

Letter To My High School Crush

First of all, I just want you to know that I didn’t plan on liking you. We were friends for a long time, and then I suddenly wished it’d be a lot more than that. I don’t know why, but I guess that’s how crushes work, don’t they? They flare up for inexplicable reasons and have a talent for making things awkward.

And, oh, it was awkward, wasn’t it? Though I never told you how I felt, sometimes I thought you knew. There were moments I’m sure it was painfully obvious, what with the staring or leaning on your shoulder or pathetic attempts at flirting. I think occasionally you avoided me because of it, which was fair. I also imagine that you never said anything because you wanted to spare my feelings.

I’m still not sure if I should be grateful for that “sparing of feelings” or not. If you’d told me you didn’t like me, I probably would have cried and felt stupid and avoided you for awhile. Okay, let’s be honest, probably I’d avoid you forever. But you know what? I still cried and felt stupid for liking you. Worse than that, I hoped. I held out. I didn’t move on until after high school because I always hoped that one day things would change between us. Holding a torch for you meant I missed out on other boys who might have liked me (and I actually did turn down a boy because of you, which is totally lame and regrettable because he was very sweet and actually pretty cute).

So I don’t think you did me any favors, though at the same time I’m sure you meant well. You were my friend, after all. It was an impossible situation. There was only one way to win and a million ways to lose.

It was all for the best, though, right? I think so. Sometimes it’s okay to lose. Sometimes it takes us where we need to be. I ended up right where I always wanted, and I hope you have, too.

Much now-totally-platonic love,



  1. Awwwww! Natalie, I´m sorry that crush didn´t work out. It´s a beautiful letter...Thanks so much for taking my dare!

  2. Aw, Natalie this is actually the sweetest thing ever. Makes me reminisce about my own past crushes. <3

  3. Haha love it!!! You were so nice!!! So sorry it didn't go as planned, but for th better right? :)

  4. I had a similar experience, Natalie! The difference is, I actually confessed. Sure, he rejected me and I cried and cried and cried but after awhile, I felt better because I regretted nothing. I still avoid him though hahahaha

  5. Natalie, this is so sweet and a little heart-breaking, and makes me remember high school so well. Thanks for sharing :)

  6. Oh Natalie, I so could've written this letter. I went through the same thing. I think maybe a lot of us did. Fantastically nostalgic post. :)

  7. I loved 'There was only one way to win and a million ways to lose.' Melted me, and took me right back to 12 years ago!

  8. Memorieeeeees. (Yes, I'm singing that) Very good letter. :)

  9. So sweet! So sweet! But man I don't miss those days for anything!!!

  10. I think it all worked out :)

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