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If they have even the slightest doubt about your intentions they will hold back.
Dating a shy man takes a lot of initial investment for an uncertain outcome.
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.
At most, it is a reliable source of advice for women who want to improve their chances with the opposite sex.
A post I made about why women shouldn't take the initiative in relationships evoked some questions about how to deal with shy men - after all, shy men don't chase women, and are unlikely to initiate anything.
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).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.Of course, he will question this over and over in his mind, wondering whether you were asking him to hang out just to be friends, or if you wanted something more.So show him that you want something more - ask repeatedly.You will probably get frustrated at his lack of response to your initiatives.