Im dating a single father
Im dating a single father - should women pursue men for dating
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.
A post I made about why women shouldn't take the initiative in relationships evoked some questions about how to deal with shy men - after all, shy men don't chase women, and are unlikely to initiate anything.
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 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.
Once this happens, you will need to gradually assume a less assertive (more traditionally female) role, because he will then be more liable to get bored with you, wonder if he could do better, consider his other options (the perception of which his newly-found confidence will likely inflate), fool around, etc.
The second caveat is that even a shy man has pride.
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.
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.