One distinction: "guess culture" isn't easy to discern from low-self-esteem culture. But "ask culture" isn't easy to discern from narcissist culture.
Service people have to cater to the lowest common denominator. Serving low-self-esteem culture just means doing the same kind of customer service one would do anyway: be clear, assure and reassure, be positive, listen closely, be understanding, consistent, etc.
Serving a narcissist is a completely different category: predict bad faith misinterpretations of your positive statements and sensible responses to them, low-key reject 2nd and 3rd attempts at bad faith misinterpretations, ignore ad hominem attacks, intuit whether their friends acknowledge the narcissism, know when to (quickly) turn them over to a manager, etc.
Consequently, some members of the "ask" group preface everything they ask with politeness or some other obvious tell to distinguish themselves. But the rest are jerks, IMO. They want to pretend that randomly requesting a free desert at an Applebee's is just a case of, "If you don't ask you won't know." But at the moment of asking, the server has to assume they are a narcissist and up their stress level accordingly. At least in America, there's no way you can be adult age without having witnessed narcissists making rando requests so that they can take out their stress/anger on service people. Given that knowledge, it's not a matter of culture-- it's just plain stubbornness and selfishness.