Getting a shy guy out of his shell?

I've been trying to text this guy every couple days. I'm pretty shy myself so I don't know how to get him into a good conversation and can only say hi and ask a few questions. Then our conversations just end. He responds to me quickly, but only with short answers. He never asks me anything or initiates, but since he responds, I'm not sure how to take this. I'm not sure if my texts are bothering him or making his day. Schools over now, but he would always stare at me from afar and his face would get really red if I sat near him. I know this is really tough and people keep telling me to give up on him, but I can't. I really like him and if he likes me, I'd like to help him overcome his shyness at least a little bit. I want to get comfortable with him. How do I go about this? Do I ask him if I'm bothering him? How do I develop a meaningful conversation that doesn't just end because neither of us know what to say? Should I be texting him at least once everyday or should I take it slow?

If it matters, he is incredibly shy. When I say this people don't seem to understand the level. He didn't even go to our high school graduation. He doesn't go out to lunch with anyone and just sits in the library by himself.

I just want to be the one who he can trust. I want to listen to him. But I first need to get to that level of trust and understanding with him.
Getting a shy guy out of his shell?
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