I think I'd expect to find Guess cultures in places and contexts which:

• are homogeneous (so that inferential distance doesn't hamper guessing)

• are rigid (implying stable roles and clear boundaries and expectations)

• are hierarchical (anticipating needs places cognitive load on the guesser and offloads it from the guessee)

• value apparent harmony (explicit refusal implies a conflict of needs)

• value apparent confidence (asking implies uncertainty)

That should suggest reasons why we find Guessiness in a lot of contexts that're notable for it. Dating, for example, isn't especially homogeneous and doesn't always break down along hierarchical lines, but harmony and confidence are very important within it.

Conversely, I think I'd expect to find Ask cultures in contexts which:

• are fluid or diverse

• value apparent egalitarianism

• value apparent ambition (explicit requests signal initiative)

• involve very high downside risk (so you can't get away with the occasional cache miss)

Haven't thought much about Tell cultures yet.