In some families, you grow up with the expectation that it's OK to ask for anything at all, but you gotta realize you might get no for an answer. This is Ask Culture.
In Guess Culture, you avoid putting a request into words unless you're pretty sure the answer will be yes. Guess Culture depends on a tight net of shared expectations. A key skill is putting out delicate feelers. If you do this with enough subtlety, you won't even 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.
My friend told me he thought of me because I'm an Asker whereas he's a Guesser (although, with time, we have probably both become more moderately so.).
For me, the problem with the Guessers is precisely that it is sometimes hard to figure out what they really mean, and as an Asker, I may easily offend them and so I may easily bad, if not guilty. Whereas I'm not subtle enough to be a Guesser, I can be sensitive enough to fear my Guesser friends may be offended which can make my life complicated at times.
So how do you recognize an Asker? Well, here's a clue :
... in many social situations (though perhaps not at work) the very fact that you're receiving an anxiety-inducing request is proof the person asking is an Asker. He or she is half-expecting you'll say no, and has no inkling of the torture you're experiencing. So say no, and see what happens. Nothing will. (The Guardian)
It's true that as an Asker, I have no problem with people telling me "no" (as long as they do nicely of course)., and I'd rather have that than a insincere 'yes' - even if I find it hard to sometimes say 'no' myself. This means these types may of course vary and we may be a bit of both, depending on the circumstances. I may also be a Guesser when I'm on the receiving end, and that's because of something else - guilt.
The Guardian column is right though that those differences are very cultural, and may partly explain cross-cultural awkwardness - between, for instance, Americans and Japanese (Japanese culture being more of a Guess Culture) but also between more similar cultures such as French and American.
My guess (no pun intended) is that generally speaking, European culture is probably more of a Guess-culture, which would make sense since it is rooted in traditions, old social codes and rather homogeneous history, whereas Americans are made up of immigrants with difference cultural backgrounds. But then, there are also huge differences within the United-States.
As my friend (who is American) reminded me, people in the Midwest - those of Nordic descent anyway - tend to be more Guessers, than, say, Cuban-American or even Californians who are mostly Askers.