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.

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That offense will reflect negatively on you and the relationship.

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

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.

The reason for this is that shy men are more concerned with avoiding the social catastrophe of asking you out and failing than they are of getting you.

This is what prevents them from taking the initiative in the first place.

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.

(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.

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.