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If they have even the slightest doubt about your intentions they will hold back.
So whatever you would normally do to indicate your interest to a confident man, double or triple it for a shy man (in proportion to his shyness): While I don't suggest that you overtly ask out a shy guy on an "official" date (this would too flagrantly undermine what he knows to be his role as described above), I do suggest that you suggest and then ask him to hang out under casual pretenses.
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." If you answer these questions sincerely and still want to date him, you then face the problem of making it happen - or rather, making him make it happen. They fall outside of the predator-prey model for sexual interactions that is assumed in the "don't initiate contact" rule.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.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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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.