Sigh. We nerds are difficult to talk to sometimes because we're so literal and we get bogged down into the semantics and completely miss the point.

No matter who asks it or at what time or because of what, the literal answer to "what's the worst that can happen" is some variation of either the universe being annihilated instantly, eternal pain and torment, etc, etc. Even your little examples pale in comparison with the worst that could happen.

So maybe that's not really the point that he's trying to make, and instead of quibbling over the semantics, we should think about what the real lesson here is.

To me, the point of this exercise is that we often get incredibly stressed out over little things without stopping to ask whether they're worth the stress we're affording them.