In my case, I'm very afraid of insisting, of imposing.
I think this is the emotional baggage we carry as LBSes. For the last 3 or 4 years of my marriage, I was trained by my ex to view every attempt at contact -- normal, marital contact -- as an intrusion into his headspace. It is going to be a difficult pattern to break.
Maybell, I've also dipped back into the dating pool and am seeing someone who I am 100% sure is interested in me. He plans great dates for us, is very affectionate, initiates contact with me almost daily -- and yet, he rarely asks me any questions about myself. I don't think he's self-centered (far from it, actually), just a nervous dater with a slightly different communication style from my own. So I've done what you've done -- adapted a bit to keep the conversation going. And I'm ok with that, given the other stuff that he's bringing to the table.