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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.
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...
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.
The second caveat is that even a shy man has pride.
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.
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.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).That offense will reflect negatively on you and the relationship.So be careful about how much (and which) initiative you take.