Rules of dating in college
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.This is what prevents them from taking the initiative in the first place.
So show him that you want something more - ask repeatedly.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.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).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.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.
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.
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.
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.