Pertaining to your update:"how do I get to the point of hanging out. As in, how would I approach someone I'm not talking to who is shy?"The answer lies in yourself. Why aren't you approaching? It's because you are shy. If you want the answer to your question, then you need to find the answer to your own issue.
Clearly, you misunderstood.
I think you misunderstand.The answer is that you simply go up to him and introduce yourself. That takes courage; courage shy people rarely have.
The question is how do I go about doing that, as to not scare him. You imbecile.
And that's what you just don't get...Good luck with that... With that attitude, you may get the shy guy, but he'll be smart enough not to stay with you.
Wow. Look old man, do you have a disorder? I'm asking how to approach it without blatantly asking him out and scaring him off. Are you dense?
Instead of the name calling and acting immature, I'll try to explain it more civily than I should have at the start.You aren't going to scare him off. Men are not deer.A shy guy is like a guy in a prison cell. He wants to get out, but he can't. All he needs is for the woman to unlock the door to the prison cell and he will come out of it and be thankful.A shy guy is the same way except that his prison cell is that he fears rejection - he doesn't fear you - he fears being rejected by you (or any other girl). That fear of rejection is so paralyzing, that a shy guy will not bother being proactive in getting into a relationship unless he has a very strong suspicion that he won't be rejected.So, very simply, if you approach the shy guy, then he will realize that he is not being rejected. His new problem is that he'd become slightly paranoid that he will blow it with you thus, be merciful if he makes mistakes because he is scared of failing and is inexperienced.
So, in summary:1. Just approach him; he won't run off but he will be scared in the sense that he's never gotten to this point before and, with so little experience, he will be afraid of making a mistake and blowing it with you.2. Make him feel at ease if he looks uncomfortable. Give him that YOU are not a deer who will run off at the slightest incorrect thing he does.3. He will make mistakes; be forgiving and reassuring.If you do these things and create an environment in which he can gradually feel safe, not only will he be yours but he'd become dedicated to you and love you more than the most loyal of dogs.... but you have to make the first move. A simple "Hi" with a simple question or two will get the ball rolling.
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Watching to many Romantic Comedies.. smh