I'll tell you from expirience Cassidy, there is nothing more freeing than telling someone you like them. Even if they turn you down and break your heart, once you tell them, you are FREE.
Free from the constant, haunting thoughts about them, free from your obsession, free from waiting, free from thinking "what if"
I went through that a couple of years ago, I was OBSESSED with this guy, totally thought I was in love with him. He was constantly invading my brain, I would go out of my way to see him, I'd take the BUS HOME when I didn't even need to just to see him.
When I finally told him I liked him, he said he didn't feel the same (in a very nice way mind you) and it broke my heart, and I cried, and I was sad for a couple of weeks, but then it was OVER. I could stop thinking "what if" and go on with my life.
So honestly honey, you just need to let him know (and TRUST ME, I know how scary it is!!!) but who knows, maybe you'll get lucky and he'll feel the same way.
pls feel free to mesage me if you need any advice or anything like that!!
I truly hope everything works out for you.
(and sorry for the tremendously long response!)