Hi Marshall, I'm not Jean but I'd like to put in my two cents with your question.
I think technology has driven us more towards ask culture than guess culture. With decreased face-to-face communication, there's now a level of disconnect between people that makes it easier for one to more confidently assert what they want. There's a shield that gives people more confidence to say and do things in general that they would not in the face-to-face presence of another person.
Furthermore, with communication like texts being ever so prevalent, it's harder to read a person's emotions, tone, etc. through a screen, so rather than play off of implications and clues, people might find it easier to just ask outright than try to scope out the situation before making a request.
What are your thoughts?