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.
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.
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 are looking for an abundance of devotion, he has it to give.
So, in conclusion, if you are interested in a shy man, start by questioning that feeling. That offense will reflect negatively on you and the relationship.So be careful about how much (and which) initiative you take.Comments like "Oh, I thought you were going drive/get the tickets/plan the trip/[insert other traditionally masculine roles here]" can help in priming his confidence if it seems to be lagging and it bothers you.Dating a shy man takes a lot of initial investment for an uncertain outcome.You will probably get frustrated at his lack of response to your initiatives.