Notes:

.There are a lot of awkward (but compelling) phrasings here, which make this exhausting and confusing (though still intriguingly novel) to read through. This post was very obviously written by someone whose first language isn't English, which has both downsides and upsides.

.Giving new names to S1 and S2 is a good decision. "Yankee" has uncomfortably specific connotations for (some) Americans though: maybe go with "Yolo" instead?

.X and Y dialogue about how they see each other, how they need to listen to each other, and how much energy they each think they need. They don't dialogue about any kind of external reality, or show off their different approaches to a real problem: the one place they mention the object level is Y 'helping' X avoid "avocado coffee", a problem which neither he nor anyone else has ever had. (Contrast the Appendix, which is more interesting and meaningful because it involves actual things which actually happened.)

But it’s still really hard for me, which is why these dialogues are the best cost-benefit I’ve found to stimulate my probabilistic thinking. Do you know of any better ones?

Play-money prediction markets (like Metaculus)?

interesting! I'm curious how the conversation between "X" and "Y" will continue