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His masculine instincts will kick in, and in some cases you can end up with a man that acts towards you the same way that a confident man would have acted from the outset.
So show him that you want something more - ask repeatedly.
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.
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.