Philosophical puzzlement: unless this does–or may–threaten the possibility of understanding altogether, then it is not the sort of thing that has worried philosophers. If you overlook that, then you do not see what the understanding is that is sought in philosophy; or what it is that may be reached. But the understanding that is sought, and the understanding that may be reached–the understanding that has been achieved if philosophical difficulty has really been resolved–is not something one could formulate; as though one could now give an account of the structure of reality, and how how language corresponds to it; and to show the possibility or reality of discourse in that way. –Rush Rhees
A most remarkable passage. There’s much that I’d like to say about it, but I want for now to limit myself to its bearing on the issue of philosophical questions and answers. Take Rhees to be pointing out just how hard it is to see how deep philosophical questions go, and so how hard it is to see how peculiar the answers to them must be.
Philosophical question threaten the very possibility of understanding altogether, but this means that the questions threaten their very possibility as questions, and threaten the very possibility of answers to them. The questions challenge the reality of discourse, of understanding: but how can a question, a mode of discourse, something that must be understood, challenge the reality of discourse or understanding? Success would seem failure; but failure cannot be success, can it? What sorts of questions are these?