Dating men down low
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.If a girl doesn't approach or initiate contact with a shy man, nothing will happen.
So, in conclusion, if you are interested in a shy man, start by questioning that feeling. 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.