In a old TV Star Trek episode Spock was asked by Kirk about what to do, and replied that there was no logical answer, thus the Kirk must rely on his human intuition.
Regarding and relative to this, we take so much for granted in discernment due to input from and to various sources, from surmising what kind of person a stranger is based upon his/her body language, speech, responses to others, etc., as well as what their speech means, parsing genre, language forms, tone, etc. body language etc., some of which is very subtle, which we progressively intuitively learn beginning in infancy, even partially in the womb to some degree.
For AI to learn such as well as humans can (which varies in ability) is likely impossible.
What you are describing is a “communication problem”.
It is incredibly complex as you say—but in my view that is an argument for AI to figure it out rather than the opposite.