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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.(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.If a girl doesn't approach or initiate contact with a shy man, nothing will happen.This is true, but handling this situation isn't as simple as you might think...

As the fear of the unknown dissipates with increased familiarity, a shy man's confidence in his interactions with you will rise.

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.

That offense will reflect negatively on you and the relationship.

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

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