So there's this guy...

[InbetweenDreams]

Your desperation is showing.

Sorry. That was blunt as fuck, but I don't mean it as in "cover it up" type of thing and move on. I mean that your desire for friendship/relationship with others is overshadowing your instinct.

Everything said in your post sounds like your instincts telling you a big fat "BAD IDEA" that you hedge around and poke at, but don't actually want to believe is true.

Listen to your instincts, yeah?

IMO, friendships (like relationships) are built on trust. If you can't trust him, he's not your friend.

I suppose it does and typically doesn't get me anywhere. In this guy's case I have a pretty good indication of what he's after and what he's like. I think perusing anything beyond friendship would be a bad idea... I'm very skeptical of people but try to give people the benefit of the doubt and seldom do things work out. It is both a good and bad thing that my intuition about people is good, I just don't always listen to it.