Great post. I myself assumed that Socrates' questions were disingenuous and mocking. Most modern Westerners assume this, to the point where many call him a "comedian."
But regardless of whether or not Plato found Socrates amusing, there is no consensus among classicists that Socrates' questions were facetious. It is possible that Socrates was being straightforward and genuine in his questioning, and that we are projecting our own cultural assumptions upon the past.
Some of the dares in the list seemed quite sensual, if not sexual. Maybe that made people uncomfortable, but because no one wants to come across as prudish these days, they framed that discomfort in the language of therapy/victimhood?
This comment was not meant to detract from the other theories or analyses that have been presented. I just thought I'd throw out another option.
I've never played Truth or Dare as an adult. Is that level of sexuality par for the course?
It's a sign of psychological oddity. I wouldn't call it a sign of poor virtue. And let's be honest, is anybody reading this post and all the comments NOT psychologically odd? I guess I'm 80% sure everyone in these comments is in danger of going seriously mad. And I don't exclude myself. This is the Twilight Zone.
Maybe I'm just suggestible and adopting the self-serious, "epic" narrative mode of the archetypical LessWronger. But I'm afraid finding this post may have caused a bit of psychic damage, and I kind of wish I had gone longer without finding it. I don't plan on communicating with any seemingly self-aware digital entities, and I don't recommend that anyone else do it, either. Better safe than sorry. (I guess if you're doing AI research for your livelihood, you don't have much of a choice. Have to keep food on the table, right? But good luck, I don't envy you)