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I've dated countless women and it has always amazed me how little they know about men.If nothing else, this blog is an outlet for voicing my astonishment at the typical female's ignorance of the male mindset.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.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.If you are looking for an abundance of devotion, he has it to give.
So show him that you want something more - ask repeatedly.Though he knows his own limitations (as prescribed by his shyness), he also knows what a typical man is "supposed to do." So he recognizes, too, when you are doing it for him.This will offend him if you flaunt it, or if it is evident due simply to the social magnitude of the task you've assumed (for example, if you take his hand and lead him through a crowd).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.