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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.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.I've dated countless women and it has always amazed me how little they know about men.If nothing else, this blog is an outlet for voicing my astonishment at the typical female's ignorance of the male mindset.If they have even the slightest doubt about your intentions they will hold back.
So be careful about how much (and which) initiative you take.
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.
Once this happens, you will need to gradually assume a less assertive (more traditionally female) role, because he will then be more liable to get bored with you, wonder if he could do better, consider his other options (the perception of which his newly-found confidence will likely inflate), fool around, etc.
The second caveat is that even a shy man has pride.