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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.

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A post I made about why women shouldn't take the initiative in relationships evoked some questions about how to deal with shy men - after all, shy men don't chase women, and are unlikely to initiate anything." 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.So it is acceptable for you to initiate with a shy guy. The problem with male shyness is that it wears off in specific situations.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.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.Unfortunately there is no quantifiable or simple rule here, as his threshold for embarrassment will vary in proportion to his shyness and his pride, which are different in every man. Well, for starters, in the early stages, you will need to give him blatant signs of your interest.Aside from their innate male tendency to overlook anything that isn't spelled out in black and white, shy men will by default doubt any sign of your affection.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...

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  1. Today’s guest blogger is Susan Cain, author of QUIET The Power of Introverts in a World That Can’t Stop Talking, available today! Are you an introvert.

  2. Things Every Extrovert Who's Dated An Introvert. Introverts need to be challenged and extroverts aren’t. Dating an introvert is the best move.

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