S4N, you need to prepare a great deal for this conversation. You need to know how you will respond in each situation and with each answer. Then you need to work on yourself so that you can be ready to manage your emotional response on each of the possible answers.
Right now everything is status quo and moving along nice and slow. But is it really moving along at all?
I think the best thing for you to do is ask him more directly about the two of you. I think you have part of your answer in that he found a place for you on craigslist. But that could be him just looking after you and thinking you aren't ready.
So broach the subject with care and understanding. Be prepared for any response and definitely be ready emotionally for negative response.
If we really want to love, we must learn how to forgive. - Mother Theresa