Hard to say more than he seems like a really nice guy just a little broken by society.
In some cultures men are beaten into submission to always pay for food. It is a custom evolved from when men purchased women for breeding heirs and when women were only allowed to be house wives. (yes I am trying to be honest...vulgar eh?) I will pay for food for people I like to be around whether woman or man. I expect the same from them. I am disgusted with women that think a man "should" pay for food. Sorry just venting.
Still it can sometimes indicate that he actually likes you. That doesn't mean he is all into having a full on relationship.
Just ask him if he likes you and take him out to eat and you pay. A good way to show him you aren't a gold digger and actually like him too. Us men like to know that you like us too! Plus it takes away the aura that you have built up around the things he buys and does for you so you can see more clearly who he is.
It definitly depends on the guy and the situation. My best friend Matt is sorta like that, but I know for a fact he does not like me. He has a girlfriend, and he considers me his little sister. But I don't know what your situation is. He could like you, but maybe not. If you really want to know, I suggest talking to him.
From what you said it does sound like he may like you then again some guys are just really nice and would do those things. How long have you two been friends?. Has he flirted with you any, does he say sweet things about you. Maybe you should just bring it up or hint around about it.
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