The last highlighted paragraph is a doozy. But it is the cult mind speaking, and we don't speak the same language anymore.
If I felt consideration for the person, I think I would just answer positively and thank him for his thoughtful response. Keep the communication as such that if down the line he had issues with JW he could approach you. I make it clear I'm happy and well and glad they are the same. It seems to befuddle the JW's I know. They expect us to be "sighing and crying" in our lives. When we are not, they seem to not know what to say.
Good luck.