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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.

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.

Unfortunately there is no easy way to discern his true intentions without putting yourself on the line over and over again, and seeing how he responds.

This can be humiliating, frustrating, even infuriating, and it can ultimately still end in failure.

Of course, he will question this over and over in his mind, wondering whether you were asking him to hang out just to be friends, or if you wanted something more.

So show him that you want something more - ask repeatedly.

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

(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.

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.

This will offend him if you flaunt it, or if it is evident due simply to the social magnitude of the task you've assumed (for example, if you take his hand and lead him through a crowd).

381 comments

  1. Thank you for this! I broke off an engagement last fall and just started dating again and the man I am currently interested in is very shy. I actually.

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