6th grade. My only defense to my awkwardness was humor.
So, I liked this girl, and for the first time wanted to do something about it.
I went out and got a "mood" ring (haha) and put in in an envelope that read:
"I like you a lot, would you care to adventure with me?"

I watched some romantic flicks and then at the end of the school day as she was walking out the school side door I called her name... well.. I think I may of screamed it. I immediately lost any bit of cool I had and lost my shit as well. She asked: "Yes"?

That is when my heart exploded, my short sword tried to hide, and I screamed (I shit you not): "MESSAGE FROM GENERAL DICK AT YOUR SERVICE."
And I ran as fast as I could after throwing the letter with the mood ring in it at her.

Next day she had the ring on gave me a kiss and we dated for some time. . . Just as well, I learned to be a wee bit more smooth given practice. I still cannot get that embarrassing ordeal out of my head.

Oh dear god... why?

Your face when.