" 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.
So it is acceptable for you to initiate with a shy guy. The problem with male shyness is that it wears off in specific situations.
If a girl doesn't approach or initiate contact with a shy man, nothing will happen.
Aside from their innate male tendency to overlook anything that isn't spelled out in black and white, shy men will by default doubt any sign of your affection.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.Comments like "Oh, I thought you were going drive/get the tickets/plan the trip/[insert other traditionally masculine roles here]" can help in priming his confidence if it seems to be lagging and it bothers you.Dating a shy man takes a lot of initial investment for an uncertain outcome.