So be careful about how much (and which) initiative you take.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 what prevents them from taking the initiative in the first place.

If they have even the slightest doubt about your intentions they will hold back.

About his past, about some current projects he's working on, etc. If I share something I'm interested in, he will ask a few questions, but he rarely initiates. I don't want to waste too much time or get any hopes up with someone that is just not into me.

I feel like if I didn't do 80% of the talking, there would be a lot of silence. If he just needs more time to feel more comfortable opening up that's fine.

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. I was much more chatty, shooting question after question at him. He rarely seems to ask things about me - more than "how was your day? No probing questions or really getting to know you questions. We started texting and flirting and our last date this week was a lot of fun.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.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, 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.