Faith, The beauty of dbing is trying new things. If something doesn't work, try something else. I would say try it, but do it in a very subtle way. You could be a little bit flirty, start w/a touch on the arm, a smile, a compliment, etc. If he pulls away, then you will know that he's not ready for any of that.
Sit quietly, the answers will reveal themselves when you least expect them to. The past is gone, the present is a gift and you need to focus on today, allow the future to reveal itself when it is ready.
