The "Ask vs Guess" name rhetorically frames it in favor of the Askers. Asking sounds reasonable, guessing does not! But really it's not about "Guessing", it's about understanding. It's about community, and relationship, and trust. What this culture really wants is for you to pay attention and understand the people around you, rather than treating everything as a transaction.
And it is guessing, because at some point it requires mind reading to accommodate. Again, most askers still understand, they are just sane enough to understand that mind reading is impossible.