I think a direct proposal would make a shy guy shocked and scared depending on how close you are. If you are quite friendly with each other, he might blush a little bit but he will appreciate your complement.
Umm. It depends on the person. When I was younger, someone had a crush on me and flat out told me, and I balked. My advice, try to build a strong friendship first. Start by saying a simple "hi" when you pass them.
Yes, truly yes. If he is insecure about himself and he sees this girl he admire far from anyone he would go crazy and avoid you as possible. He wouldn't even would dare to look you in the eyes when your flirting with him because he feels this great feeling that overwhelms him. But don't let yourself down, be nice to him and give him advise on how to build self-confidence. It may take time for him to open up but you'll always know when he loves you.
oh honey trust me, been there done that! i just walked up to him and i was like "so, i know you think this is really weird but i kind of like you"... but anyways it depends on the guy, what he's like. sporty jocky guys tend to think it's a bit weird or crazy, but down to earth guys would totally understand, even if they didn't like you back. just try to truly figure out what kind of person he is, and work from there. ;)
i am that kind of guy. my girlfriend liked me since october 2010, and weve been dating for a little less than a year. i was, and still am a shy kind of person. you just need to approach him slowly, and get to know him well as a friend before you do something like that, or else it will startle him. that way, you might even win him.