Thanks for the personal example!
That's what I've been trying to do. When he asks me how I feel about him I try to give very specific answers, I like __________ about you. I have to push myself to say what I really feel, even if it makes me feel vulnerable, and be careful not to say I feel more than I do because he would see right through that (even though its tempting to do so to make him feel better).
The more time that passes the less insecure he seems and the easier we can talk about our feelings. And the "feelings talk" usually only happens after we've already talked about everything else for hours. I feel like we are on the right track I'm just looking for some reassurance.