Andrea Donderi says there are two types of people in the world: Askers and Guessers:
“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.”
Thank you Erika for pointing me to this article after I expressed on Twitter how I have a hard time asking for favors. Definitely giving this some more thought.