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The second caveat is that even a shy man has pride.
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.
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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.
This is true, but handling this situation isn't as simple as you might think...
The first thing to do when you find yourself attracted to a shy man is to question your feelings for him.
In other words, ask yourself "Am I attracted in spite of or because of his shyness? A very close friend of mine is extremely shy, and I know plenty of other guys that are shy. Shy guys, almost by definition, do not have the balls to initiate and pursue women.
" If you answer these questions sincerely and still want to date him, you then face the problem of making it happen - or rather, making him make it happen. They fall outside of the predator-prey model for sexual interactions that is assumed in the "don't initiate contact" rule.
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).