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.
(If nothing else, this will give you good insight into what it is like to be a man.) While all of this sounds like it might be too difficult to deal with - and many women will come to that conclusion - it is worth pointing out that if you can navigate through the difficult aspects of attracting and dating a shy man, he is likely to be completely faithful to you.
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...
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.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.At most, it is a reliable source of advice for women who want to improve their chances with the opposite sex.A post I made about why women shouldn't take the initiative in relationships evoked some questions about how to deal with shy men - after all, shy men don't chase women, and are unlikely to initiate anything." 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.