My high school is really small, about 150 kids total in grades 7th-12th. One of my classes had 3 people in it and my favorite teacher. My favorite teacher also happened to have "lunch duty" (where there would be two teachers keeping watch while we ate/had "recess"). Our recess was mostly in the old gymnasium, where we'd sit in the bleachers across from the teachers watching us. Anyways, I always sat with my close friend in the bleachers. He wasn't necessarily shy, but he never really talked to anyone other than me and a few of his other friends. He was also extremely good looking and I'm pretty sure every girl had a crush on him. We would sit together, just the two of us, talking and laughing until lunch/recess was over.
Whenever I'd have class with my favorite teacher, she'd try to play match maker and talk me into dating him. I never really had /those/ type of feelings for him up until my teacher started doing this. She would say "he totally flirts with you! I watch you guys all the time!" and stuff like that. I did start to notice he'd flirt with me, but I was pretty shy and never really thought he actually liked me like that.
We won a trip to Washington, D.C. together.. this is when I really noticed some of his flirting. I remember he brought his laptop and we watched a movie together while sharing ear buds. We laughed and joked about so many stupid things in D.C. We watched the changing of the guards and it was really windy out. I told my other friend (a girl) who also won the trip that I was freezing balls. He gave me his jacket. I told him I didn't need it but he insisted. I also remember when we went to the murals and such at night, we stood by this waterfall thing and took a really cute picture, ngl. One of our treats for being well behaved on this trip was that we got to go to the movies. On the bus on the way back, this is when I decided, what the heck. Let's see if he likes me. I told him I was kinda tired and asked if I could rest my head on his shoulder, and he was all "sure!". I remember my female friend in the aisle next to me smiling so big and cheering me on, LOL. (I now realize that all of this could just be a best friend being nice to his best friend, and NOT flirting, but I was dumb at the time. sorry!!~)
A few weeks after we got back from D.C., we were in our usual spot in the gym. I decided I might as well tell him and see what happens. I was soososososo nervous. I remember staring at the time on my phone, making sure I say it before the bell rang (as I had missed previous attempts to tell him before because I was too scared~~). Sooo.. I just kinda came out with it.
"So, hey. You know I like you, right?"
"What?"
"I kinda like you.. uh.. is that cool?"
"Sure..."
~*awkward silence for the longest 5 minutes of my life until the bell rings. we awkwardly get up and walk towards the hallway together*~
I don't even remember if anything was said after the "sure" or the walk back to classes. I've pushed that memory so far into the back of my mind, not even sure if the above conversation is 100% accurate. He wasn't in my grade, so I didn't have to go to the same class room as him. All I remember is slamming my head into the desk while thinking FUDGE.
Basically, nothing ever came of it. It messed me up for awhile, as I couldn't see why he didn't feel the same way because we were pretty much twins since we had so much in common. We had the same sense of humor and everything!

I think it was because I'm not that attractive to him, though, and he started to discover how badly all the girls wanted him. He ended up supposedly knocking up some chick and he smokes weed/drinks heavily now. I kinda wish we were still close so he wouldn't have gone down such a bad path, but then again, that's not my problem. ~