I've had this HUGE crush on this guy for 11 years, we are both 16 now. I don't know what to do, this "obsession" is eating me alive. He is a great guy, and yeah he is a bit shy but he is amazing. We are not friends friends, but close to it. Over the years I've cought him staring at me whenever he hang out with our friends, but we've had like 5 conversations in all of the years that we've known each other. He once asked me to be his valentine when we were in 6th grade but I'm 87% sure that it was a dare. Last year he was dared to kiss me, but he chickened out.
He has never tried to even talk to me, and he has "dated" other girls but I don't know, I can't seem to get over him no matter how hard I try and it's driving me insane. Can someone please tell me if I should tell him how I feel (I'm pretty sure that he knows because all of my friends know and they are always messing with me in front of him, but this was like three years ago) or if I should at least try to be his friend and never try anything or wait until he comes up to me oh my gosh I don't know please help me, I'm pretty sure I'm in love with him..
I don't know about him, but if I were him it seems like I would love if you just came up to "me" and express your feelings. I don't think that you should tell him how long you have been interested at first because it could turn him off. It could make you look a bit weird, but if you develop a strong relationship, you will be able to tell him in time definitely. What's the worst that could happen? I bet you would still be friends, and hey may even reconsider his answer. Good luck to you!
Just indirectly ask him out, ''do you wanna grab a coffee sometimes, you and me? :)'' He will get it. Don't suddenly come out with I LIKE YOU, imagine a guy did that to a girl, he will INSTANTLY, INSTANTLY got friendzoned...