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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.

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).

Comments like "Oh, I thought you were going drive/get the tickets/plan the trip/[insert other traditionally masculine roles here]" can help in priming his confidence if it seems to be lagging and it bothers you.

Dating a shy man takes a lot of initial investment for an uncertain outcome.

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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.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.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.This can be humiliating, frustrating, even infuriating, and it can ultimately still end in failure.If a girl doesn't approach or initiate contact with a shy man, nothing will happen.