[yodon]

I'm wondering if you may have rediscovered the concept of "Wicked Problems", which have been studied in system analysis and sociology since the 1970's (I'd cite the Wikipedia page, but I've never been particularly fond of Wikipedia's write up on them). They may be worth reading up on if you're not familiar with them.

[Agraillo]

It's interesting. The question from the paper "Darling, please be honest: have I gained weight?" assumes that the "socially acceptability" of the answer should be taken into account. In this case the problem fits the "Wickedness" (Wikipedia's quote is "Classic examples of wicked problems include economic, environmental, and political issues"). But taken formally, and with the ability for LLM to ask questions in return to decrease formal uncertainty ("Please, give me several full photos of yourself from the past year to evaluate"), it is not "wicked" at all. This example alone makes the topic very uncertain in itself

[ICBTheory]

Wow, that is a great advice. Never heard of them - and they seem to fit perfectly into the whole concept THANK YOU! :-)