Rules in dating
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.The first thing to do when you find yourself attracted to a shy man is to question your feelings for him.In other words, ask yourself "Am I attracted in spite of or because of his shyness? A very close friend of mine is extremely shy, and I know plenty of other guys that are shy. Shy guys, almost by definition, do not have the balls to initiate and pursue women.That offense will reflect negatively on you and the relationship.So be careful about how much (and which) initiative you take.Unfortunately there is no easy way to discern his true intentions without putting yourself on the line over and over again, and seeing how he responds.This can be humiliating, frustrating, even infuriating, and it can ultimately still end in failure.
As the fear of the unknown dissipates with increased familiarity, a shy man's confidence in his interactions with you will rise.
In general, you will need to carry the relationship up until the point that it is "official." When it has been established (or is otherwise clear) that the two of you are together, then you should start reducing your initiative and letting him take the reins.
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.
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.