I find it odd that he's asking if YOU think it's time. If HE thinks it's time, why can't he come out and say that. Trying to place the decision on you?
I was kind of thinking the same thing. Like he's feeling you out. My H did the same right before we were scheduled for our first mediation. I could be mind reading but just a thought
I would maybe shorten the reply some. This is not what I want but I won't stop you on your path to happiness. I know I can be happy too.