A shy man may never become courageous enough to approach women in general, but he can eventually grow comfortable with a girlfriend or wife.As the fear of the unknown dissipates with increased familiarity, a shy man's confidence in his interactions with you will rise.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.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.
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.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.You will probably get frustrated at his lack of response to your initiatives.