Yeah, definately show him some signs. See, if I really flirt with a girl, and she doesn't show anything back, then I get discouraged. I ended up missing an oportunity like that, and I was pissed when I found out. But hey, wtf was I supposed to do when to me it seemed like I was just making an ass of myself.

You don't have to come straight at him, but push back a little, or push back more, just push. Then it will make it easier when you feel you can put it out there.