When I thought he was going to a place I didn't want him to go I said to him I'm not going to answer any of your questions because I've been on the other side before and I know what to expect and that's when he laughed and promised me assured me that was not his intention whatsoever-
Now I wonder if he himself was reaching out. Maybe he's the one who's curious about the other side. If he's been in the WT organization for that long, chances are he's seeing and feeling the changes that are not too kind for old timers who have sacrificed so much of their lives. Maybe he's feeling too lonely in his congregation. I know how sometimes "uncool" JWs get as shunned even thought they are JWs in good standing.
I'd be thrilled if there will be more conversations. I hope you left the door open for him.