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When he wasn’t writing creatively, he was writing about how much writing he was doing. John III is a musician and producer who owns an independent record label in Chicago.

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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.

That offense will reflect negatively on you and the relationship.

So be careful about how much (and which) initiative you take.

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.

If nothing else, this blog is an outlet for voicing my astonishment at the typical female's ignorance of the male mindset.

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.

Dating a shy man takes a lot of initial investment for an uncertain outcome.

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.