Maybe gently point out one thing, or perhaps two, no more. He might appreciate a little help. Make it something fun and/or easy for him to do. Like he could think up a date. It might be time to try just the slightest bit of a push. My two cents, anyway. Remember, experiement and see what works, if it doesn't, back away quickly but calmly and smoothly.
I think those positive, upbeat conversations are a great sign!
Good luck, dear Wonder. And thank you for your big, juicy hug. It gave me courage for tonight!