Trying to divine what is in their minds from the entrails of song choices will drive you mad...lol...trust me, been that and done there.
Plus it is addicting...
Sounds like some cracks may be appearing in "The Wall"...Ha!
I think you are doing the right thing to let him approach you with any sharing of info from C...it can stir up stuff, unsettle things a bit. He will share when he has processed some of it, W did A LOT of that with me this late winter and early spring. We are still the most trusted, even if said status is unacknowledged, person in their lives.
Just keep being your most awesomeness-defined self, Raine...you're getting there, he is noticing, taking baby steps....
In the depths of winter, I finally learned that within me there lay an invincible summer. - Albert Camus
Uncertainty is the very condition which impels people to unfold their powers.-Eric Fromm