In my opinion, I feel you should enjoy reminiscing and hold off on the JW stuff. I would be kind about it too when it did come up. Remember the saying, "You can win the battle, but lose the war." If you come on strong he's going to pull away. So then what was accomplished? That's the bottom line here. What end result would you like to see? And what is the best way to get there.
Remember what your mindset was while in. Wouldn't you have put up your guard when someone spoke against the organization? I know I would have.
Juni
Edited to add: Sounds like we're both on the same page after I read your latest response.