Haven't been this confused in a long time.

Hi, there. It sounds like you have a bit to work through, here. Mostly it seems to be stuff you've internalized about yourself. Poor self-esteem can be pretty debilitating in your day-to-day life; it can impact how you feel about yourself in public, perhaps even dissuade you from going out and doing things that are otherwise simple and can make interactions with others seem insurmountable.

But regarding your friend in particular: the only way you'll know what he thinks or feels about you is if you either ask him or he tells you point-blank. But considering you don't think you necessarily want him to have feelings for you, it's probably better to sort out your feelings before putting your friendship at risk (which, unfortunately is something that can happen when you confess having feelings for a friend). You sound like you're in a pretty vulnerable place, so whatever you decide, just be careful.