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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.
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.
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).
A shy man may never become courageous enough to approach women in general, but he can eventually grow comfortable with a girlfriend or wife.