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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.
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.
So, if you do choose to initiate, do so only during the early stages of dating, that is, until he builds his confidence and comfort around you.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.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.
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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.