Another writer and I once decided to engineer a meeting between Diogenes and Socrates.
It is possible that they met in real life. The Athenian army (of which Socrates was but one lowly soldier) were sailing to lay siege to Syracuse In Sicily (a possible colony and a way to remove the over-lordship of the Spartans, ((Lacedaemonian)) They marched past and stayed for the night near the city of Thebes. It was there that Diogenes lived in his fabled clay pot and it is possible that the fathers of Stoicism and Morality once met. Though "if" they did, no record was ever made of the meeting So a fellow writer and friend of mine and I decided to write that meeting.
It was a disaster. Always remembering a little more, trying to change each argument, doomed to failure. Ended up in a wastepaper bin.
It is also worth noting that Demosthenes (the father of democracy) and (or so it is rumored) Alcibiades himself marched with the same army. It is still a tempting thought. Put the four of them together in a tent (or indeed a clay pot) and imagine the discussion. Cool huh.
Lol- but I am not thinking of even attempting it.