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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 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.
As the fear of the unknown dissipates with increased familiarity, a shy man's confidence in his interactions with you will rise.
His masculine instincts will kick in, and in some cases you can end up with a man that acts towards you the same way that a confident man would have acted from the outset.
So it is acceptable for you to initiate with a shy guy. The problem with male shyness is that it wears off in specific situations.
A shy man may never become courageous enough to approach women in general, but he can eventually grow comfortable with a girlfriend or wife.
The second caveat is that even a shy man has pride.
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.
The first thing to do when you find yourself attracted to a shy man is to question your feelings 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).That offense will reflect negatively on you and the relationship.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.Once this happens, you will need to gradually assume a less assertive (more traditionally female) role, because he will then be more liable to get bored with you, wonder if he could do better, consider his other options (the perception of which his newly-found confidence will likely inflate), fool around, etc.
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