In my opinion, I feel the fact that you two live in different cities should make things easier if you needed to vent your feelings. It’s not like you see him every day, so what’s the worst that could happen? Have you ever noticed you regret not doing something more times than you regret doing something? It couldn’t hurt to put your feelings out there. It wouldn’t ruin a friendship, it may make things a little akward if the feelings aren’t returned, but awkwardness goes away in time. It’ll give you more practice in speaking your voice when you really want something out.
You don’t need to be blunt about it and say ‘HEY I LIKE YOU.’ But casually bring it up, asking if he’s dating anyone first… then he’ll recipricate. Or say so have you met anyone, and when he asks you, just say no, but I do have feelings for you and it’s something I wanted to get off my chest. The very worst thing he could say is I’m sorry.
I’m sorry, I know that sounds a little middle-schoolish. But it always seems to work on my part. I hope you figure things out!
