It doesn't sound to me like you're having a road-block, sweetie.
What happens in our daily lives really is how we learn about one another and get to know other people. And that can often be more illuminating than say, where you were born, how many partners you have had or what your goals are, if that makes sense.
It sounds to me, though, like perhaps he just is looking for other modes of communication, so perhaps the next time he asks that, you should simply say that you can't really think of set questions like that, but if he wants to ask YOU anything, he certainly can, and that he shouldn't take your not asking him those things as disinterest in him.
If and when he comes back you both feel stilted in talking, where it goes from there will be up to you. Obviously, a partner we can't talk to isn't a good partner for us. But for the time being, it doesn't sound to me like that is an issue.
I would take a look at you goal of "being together as long as you can," however. THe quality of a relationship really can't be charted by how long or short a time we are with someone, and if things aren't good in the now, it doesn't really matter how long something goes on for, does it? maybe you might want to consider adapting that goal to, say, enjoying the time you DO spend together as much as possible. Might also take the pressure off a bit.
Editor and Founder, Scarleteen
My epitaph should read: "She worked herself into this ground."
-- Kay Bailey Hutchinson