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