Yeah, I know what you mean. I have been in your situation before....and that was back in high school. I liked one of the smartest/ most popular guys in school.....and was too chicken to start up anything with him while I had the chance. We did speak a few times during the 4 yrs but it was becuz we were in some of the same after school activities. It was just really hard to look him in the eye or say anything to him... or actually really get to know him....
Anyways...
So, I figured I would wait until graduation night to give him a note....to tell him what I thought about him etc. Mainly I chose then becuz I figured well..I would probably never see him again since he was going to college out of state. But well, I chickened out yet again....
So time went on.....and college started in fall and I kept wondering, what if I would have just got that off my chest and told him how I felt. It literally drove me nuts.... So one night I got on my computer and looked him up on his university website and wrote him an email.... I explained to him how much I liked him etc and how I was kinda too chicken to do anything about it... Surprisingly, He wrote me back......AND he remembered me. (mainly cuz of the after school activiities etc.) Anyways....he felt bad that I felt I couldn't approach him and said he felt really flattered. He also said that had I asked him out, he would have given me a chance... But seeing he was three states away and planning on staying there for 4 yrs and then going on to grad school for another 2.....there was really no way we could even start anything up. So, I left it at that.
Ok, so in a way I was relieved....and yet kinda mortified. Im sure he was kinda like wtf? But, anyways, it helped me move on. I saw him once or twice after that while he was home on break......and he was actually very friendly and said hi and all that. I still was shy as ever....but as time went on ......I eventually let it go... and dated other people that I actually felt comfortable enough around to talk to.
Keep in mind, this all happened 7 yrs ago already....and I have moved on....and life has definately changed since then....
Anyways, whatever you plan on doing.....I think you should get to the bottom of it. At least find out. I know it drove me nuts until I did.....and even though I regret not going for it while I could have had the chance in high school, Im glad I got that closure afterwards, even if i Did feel stupid afterwards in a way... And since then I realized that its worth that shot to find out whether I have a chance or not. At least then I know...
Good Luck!
