Men who have no interest in dating
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.
This is true, but handling this situation isn't as simple as you might think...
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.
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 you are looking for an abundance of devotion, he has it to give.