Just a quick update as I have to run off to school. What I ended up doing was saying the above to him last night, less the item I had issue with. He said thanks, that it meant everything and gave him incentive to keep trying. I have to do it in the evening because I don't see him in the morning and didn't think text was appropriate.
I also asked him about the book and he said he would love to do it together. I already finished it but plan on going through it again. What a great book! I really feel like it screams to both his and my issues. I ordered one so I can mark it up with notes. I just left it up to him as to when/how to go about it.