Search Results: give him the confidence to ask me out

I'm pretty socially oblivious, nice, non-talkative. I don't say things unless they seem relevant, as in I don't just talk for the sake of airing my thoughts. I feel like it makes me the needlessly strong silent type to some people that appear to like my company. I'm often unsure if I should even CARE whether or not people see my "sensitive" side or the underlying madness I impulsively suppress. (I assume most people have the underlying madness?). By "open up" I guess I mean express that I'm kinda oblivious and often choose inaction instead of being a fuck up in situations where it wouldn't be funny... worries, etc. or somehow insinuate they seem like good people, persons I'd hang out with, maybe steal friends from. And hope I don't have to figure out more obvious ways to fish for rejection.
(don't give me crap about having confidence, my only confidence is in things that are clearly relevant or knowing what I'm actually capable of doing. I don't understand the "hey look at me! I'm awesome!" confidence. It looks like a joke I don't get.) big parentheses.

These people, acquaintances, are just people I see in my regular life occasionally cause they work places or used to and bump into me. We talk, have funny conversations, some I've "known" for more than 2 years. Like my tattoo guy, this girl who works at a pipe shop with the lowest prices, one of my makeshift supervisors at work, other people I can't think of off hand.

So I guess I could ask this a couple of ways:

Would you gagger people go about making friends with new other people this way?

-or-

Should I make an effort to open up to these nice acquaintances?

basically same question.