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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.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.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.The second caveat is that even a shy man has pride.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.The first thing to do when you find yourself attracted to a shy man is to question your feelings for him.

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

(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.

In general, you will need to carry the relationship up until the point that it is "official." When it has been established (or is otherwise clear) that the two of you are together, then you should start reducing your initiative and letting him take the reins.

As I said, he will probably start to do this on his own anyway, so rather than forcing it, just be cognizant of the transition.

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I also have both short and long term goals for doing so. So please save the condescending lectures (and arm-chair therapy) for someone else.

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