>>If I see a glaring error or if I need more clarification/criteria,
>>I will seek that.
Bollocks. Your technique is ......
1) Raise a scenario which is problematic for the persons position.
2) Get the person to EITHER defend the scenario OR acknowledge that you have committed a coup.
3) If scenario appears to fail.......extend scenario or replace with new scenario.

You don't start off with "could you clarify something because
I may have misunderstood........".

If someone says "I don't think I would have been traumatized at 15 with a sexy
schoolmistress" and you follow that with
a) "so you think its okay for adults to fuck children"?
b) "so you think its okay for 15 year old boys to fuck 30 year old men"?
I mean....you're not really in a discovery process here ..... are you?

You are being entirely to kind to yourself.