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That offense will reflect negatively on you and the relationship.So be careful about how much (and which) initiative you take.In general, you will need to carry the relationship up until the point that it is "official." When it has been established (or is otherwise clear) that the two of you are together, then you should start reducing your initiative and letting him take the reins.As I said, he will probably start to do this on his own anyway, so rather than forcing it, just be cognizant of the transition.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.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.
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.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).