It's worth considering that you might not have understood his argument. I had a friend who often had this issue, where if we started discussing something, they'

It's worth considering that you might not have understood his argument. I had a friend who often had this issue, where if we started discussing something, they'd just endlessly pester me with "but why?" and then declare an "ego protection" when I inevitably said something that could be construed as rejecting reality even if that wasn't what the point was, and they weren't doing this maliciously, they just genuinely thought this way. Eg if the discussion were about Spotify opposing Apple's exploitative fees, and my position were that it doesn't matter that Spotify is just supporting that position for the money, as long as it's aligned with consumer interests. They might've managed to pester me into saying "the truth doesn't matter" and declared that to be a fault in my position, even though that's a perfectly valid argument in this context.