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" 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.
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).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.
The reason for this is that shy men are more concerned with avoiding the social catastrophe of asking you out and failing than they are of getting you.