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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.
Unfortunately there is no quantifiable or simple rule here, as his threshold for embarrassment will vary in proportion to his shyness and his pride, which are different in every man. Well, for starters, in the early stages, you will need to give him blatant signs of your interest.
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.
Dating a shy man takes a lot of initial investment for an uncertain outcome.
If a girl doesn't approach or initiate contact with a shy man, nothing will happen.
This is true, but handling this situation isn't as simple as you might think...
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.