Funny, WCW...here we are, trading places for a bit....
I'm backing off from the R talk, and you're pushing forward with it, bit by bit!
So, some lessons I learned in R talk (believe it or not, I learned some!): go slow, since both of you have not done it for a while. Safe environment, your tone, face expression, ease will convey that he is safe. May want to start off expressing, gently, your thoughts on what you would like, in a caring way, and compliment him (not overboard) to get his ego boosted before hammering at questions about his plans (learned this the hard way). When you state your feelings, they are just that, put them out there, but no expectations of him doing anything about it. Just relax, do at least 1 thing to make him comfortable...even if it's a small smile during the hard conversation. You'll be great!