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.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.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.
Due to the lack of female attention he has attracted or received, he is like an emotional spring that you will release.
" 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.
You will probably get frustrated at his lack of response to your initiatives.
The biggest problem is that it won't be clear to you whether or not his unresponsiveness is a product of his shyness or his lack of interest in you - because it could be either one. His persistent willingness to hang out with you might be stem from a real interest, but it also might be a manifestation of his unfulfilled desire for female attention; he could just enjoy dabbling in the idea of a relationship but at the same time not like you enough to want anything serious with you.