Oliver Burkeman picks up a great idea first floated by blog commentator Andrea Donderiand and runs with it:

We are raised, the theory runs, in one of two cultures. In Ask culture, people grow up believing they can ask for anything – a favour, a pay rise– fully realising the answer may be no. In Guess culture, by contrast, you avoid "putting a request into words unless you're pretty sure the answer will be yes… A key skill is putting out delicate feelers. If you do this with enough subtlety, you won't have to make the request directly; you'll get an offer. Even then, the offer may be genuine or pro forma; it takes yet more skill and delicacy to discern whether you should accept."
Neither's "wrong", but when an Asker meets a Guesser, unpleasantness results. An Asker won't think it's rude to request two weeks in your spare room, but a Guess culture person will hear it as presumptuous and resent the agony involved in saying no. Your boss, asking for a project to be finished early, may be an overdemanding boor – or just an Asker, who's assuming you might decline. If you're a Guesser, you'll hear it as an expectation. This is a spectrum, not a dichotomy, and it explains cross-cultural awkwardnesses, too: Brits and Americans get discombobulated doing business in Japan, because it's a Guess culture, yet experience Russians as rude, because they're diehard Askers.

This is actually pretty simple: Guessers are wrong, and Askers are right. Asking is how you actually determine what the Asker wants and the giver is willing to receive. Guessing culture is a recipe for frustration.

What's more, Guessers, who are usually trying to be nice and are holding themselves to a higher level of politeness, ruin things for the rest of us. I'm not a super hospitable guy, but I frequently find myself offering things to other people that I'd like them to take -- say, leave their kids at my house to play with my kids -- but they refuse to take because they think I'm a Guesser, offering hospitality I secretly hope will be turned down. Guessers are what forces people with poor social discernment, like me, to regard all kinds of interactions as a minefield of awkwardness.

Maybe the next best thing to everybody becoming an Asker would be for more people to be aware of the two categories. That way, when you meet somebody in a situation where this sort of confusion might pop up, you could just state whether you're a Guesser or an Asker and adjust accordingly.