Rules for dating on the internet
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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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.
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 you are looking for an abundance of devotion, he has it to give.
So, in conclusion, if you are interested in a shy man, start by questioning that feeling.
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.
Comments like "Oh, I thought you were going drive/get the tickets/plan the trip/[insert other traditionally masculine roles here]" can help in priming his confidence if it seems to be lagging and it bothers you.