You will probably get frustrated at his lack of response to your initiatives.
The biggest problem is that it won't be clear to you whether or not his unresponsiveness is a product of his shyness or his lack of interest in you - because it could be either one. His persistent willingness to hang out with you might be stem from a real interest, but it also might be a manifestation of his unfulfilled desire for female attention; he could just enjoy dabbling in the idea of a relationship but at the same time not like you enough to want anything serious with you.
" If you answer these questions sincerely and still want to date him, you then face the problem of making it happen - or rather, making him make it happen. They fall outside of the predator-prey model for sexual interactions that is assumed in the "don't initiate contact" rule.
As I said, he will probably start to do this on his own anyway, so rather than forcing it, just be cognizant of the transition.The reason for this is that shy men are more concerned with avoiding the social catastrophe of asking you out and failing than they are of getting you.This is what prevents them from taking the initiative in the first place.If a girl doesn't approach or initiate contact with a shy man, nothing will happen.This is true, but handling this situation isn't as simple as you might think...