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.(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.I've dated countless women and it has always amazed me how little they know about men.
So be careful about how much (and which) initiative you take.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." 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.A shy man may never become courageous enough to approach women in general, but he can eventually grow comfortable with a girlfriend or wife.