Politics related, niche interest related, meme related - surprise me.
E.g. "what's the temperature going to be like today?"
I'll answer "it's going to be pretty cold."
Then you edit the question to be "can you give me a hint about which layer of hell Henry Kissinger is going to?"
Just FYI it's unlikely someone with pronouns set to comrade/them want to be referred to as dude or man