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A shy man may never become courageous enough to approach women in general, but he can eventually grow comfortable with a girlfriend or wife.
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).
(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.
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, if you do choose to initiate, do so only during the early stages of dating, that is, until he builds his confidence and comfort around 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.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 a girl doesn't approach or initiate contact with a shy man, nothing will happen.