Sorry this is happening but I found some humor in that conversation you wrote. I agree with all the posters but especially Soul Quake -tell him nicely that you won't engage in answering questions lie this. When he does it, remind him of your agreement and don't answer him.

I agree with Rhiannon, does he show any symptoms of OCD? He sounds very insecure and this is his problem not yours. If that were me, I turn it around and say "I don't know, what do you think" lol??