Search Results: men who do everything to make them happy

I've had this guy friend since high school that, apparently, has had feelings for me for a year or so. He no longer lives in my state due to family relocation, etc. Deep down I know he could be a really great man, but he has little faith in himself. So, with my high level of empathy, I feel the need to make him see himself for who he truly is. We were having discussions quite frequently, often of more sexual nature, which led to the inevitable question: Should we stop doing this to ourselves and just be friends, or continue on this emotional roller coaster of "I want to be with you, but I can't." (because of distance, etc.)?
This eventually all got too exhausting, so I said I'd leave it up to him, (mostly because I know what I wish would happen, and I know it's not plausible at the moment) I told him that I didn't want to sway his decision either way, because I want him to be happy as well. We didn't speak for a short while, and when we began speaking again everything felt fairly closed off, and I didn't know where we stood, so I made feeble attempts at directing the conversation to those similar to past we'd had. Needless to say, he never 'caught on' & somewhere amidst this he'd decided to be friends and never made me aware of it, so I made a pretty huge ass of myself for a while. It feels a like he doesn't know what he really wants & I don't have much experience to go off of, so I'm mainly wondering if I should believe him when he says that the reasons he doesn't contact me and I'm always the one initiating conversation is because "he doesn't really know what to say," is it all just bad timing and should I get over my feelings for him before they even take off? Or should I just sit tight and play this whole "friends" thing out? On several occasions he's straight out asked what I want him to say, and told me to communicate these things, but that feels like I'm forcing feelings that aren't real. Shouldn't he be able to express his feelings on his own?