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.

At most, it is a reliable source of advice for women who want to improve their chances with the opposite sex.

" 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.

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.

A shy man may never become courageous enough to approach women in general, but he can eventually grow comfortable with a girlfriend or wife.

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

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.

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.