As a product of Southern American culture, I would note that "guess" culture as described here - specifically, the preference for indirectness and inference - is always something that exists primarily in and near interaction among strangers. It doesn't always disappear entirely in familiar relationships, but does abate significantly in favor of being more direct. (Of course, this in itself increases the chance of cultural mismatches causing conflict, as what's ordinary for someone from an "ask" culture can easily read as an insulting assumption of excess familiarity for someone raised with "guess".)

That said, it is important to keep in mind that what's here under discussion is a broad and fairly imprecise description of how varying acculturation can affect interpersonal relationships mostly among people who don't know one another all that well. In that context it's useful; to try to generalize it to every human interaction is not.