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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.
All kinds of problems spring up around the edges. If you're a Guess Culture person -- and you obviously are -- then unwelcome requests from Ask Culture people seem presumptuous and out of line, and you're likely to feel angry, uncomfortable, and manipulated.
If you're an Ask Culture person, Guess Culture behavior can seem incomprehensible, inconsistent, and rife with passive aggression.
Obviously she's an Ask and you're a Guess. (I'm a Guess too. Let me tell you, it's great for, say, reading nuanced and subtle novels; not so great for, say, dating and getting raises.)
Thing is, Guess behaviors only work among a subset of other Guess people -- ones who share a fairly specific set of expectations and signalling techniques. The farther you get from your own family and friends and subculture, the more you'll have to embrace Ask behavior. Otherwise you'll spend your life in a cloud of mild outrage at (pace Moomin fans) the Cluelessness of Everyone.
As you read through the responses to this question, you can easily see who the Guess and the Ask commenters are. It's an interesting exercise.