Jean Hsu's article on Ask vs Guess Culture is a great read:
If you’re more a guess-culture person, asking people for help without knowing their circumstances can feel rude or intrusive. Broadcasting publicly your need for help can feel awkward and vulnerable.
If you’re more of an ask-culture person, the guess-culture example of juggling everyone’s specific scenarios and the historical context of favors probably seems exhausting. Dropping hints in the hopes that you won’t even have to make your request can feel extra passive and manipulative.
And because I'm an Asian living in the U.S., I experience so much clash between the cultures:
I was raised deeply in guess culture, as many Asians and Asian-Americans are. The Japanese proverb that “the nail that sticks up gets nailed down” reinforces the idea of social collectivism and keeping your individual needs and wants to yourself — values that are shared by many Asian culture.
Western society is very much ask culture. A classic example can be found in proverbs. “A squeaky wheel gets the grease” is an American proverb, enforcing the ideas of individualism and that asking for what you want will benefit you.