My favourite example of a "Guess culture" is that of Iranian taarof[0]:
Another example occurs if a Western individual is not familiar with taarof in Iranian culture. When an Iranian individual is offering taarof, it is to first view it as a sincere offer with the hope of decline up to four or five times. If the individual offers more than five times, it can be concluded that the individual is not doing taarof, and the opposite side should respectfully thank that individual and accept the offer with gratitude.
In that example one has to decline about 5 times (!) to be sure the offer is genuine, most people unfamiliar with that custom will take the offer the second or third time or will be enraged that they don't understand a "No, thank you".
The most laborious combination is a "genuine offer" and you deciding to decline it. The person signaling the genuine offer will try to double down, - so expect an 8th time - until your genuine rejection is "accepted" and while you are at it firmly holding your ground try to sneak in a counter-offer, too ;) In the end you will end up most likely accepting a "symbolic offer" of the genuine offer. E.g. if you decline a ride you are offered genuinely (say because you want to have a comfortable ride with a taxi), you can decline eventually by accepting the symbolic offer that e.g. a taxi is called up for you.
Pretty hard to figure out if you are coming from an ask culture.