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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.
This can be humiliating, frustrating, even infuriating, and it can ultimately still end in failure.
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.
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.
Due to the lack of female attention he has attracted or received, he is like an emotional spring that you will release.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...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.