It is so frustrating. In my circle of companions growing up, I was always the devil's advocate. It was just part of the group's acceptance that I would likely challenge most anything, whether due to serious opposition or just for the mental exercise of exhausting alternatives. It was never personal, nor done to annoy, just to stimulate thought, and to prevent lazy decisions. I think we were all a pretty deep thought kinda crew. That was a long time ago.
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I love it, for the mental exercise. Just a nice back and forth to not be lazy about decisions!