I think it requires emotional intelligence to know if you should ask or guess.

I've encountered a few people that just won't stop asking for unreasonable things, and it destroys the relationship very quickly, because they just won't take no for an answer. I also have one child that I used to have to firmly say "stop asking for things" once it would get out of hand.

But those are extremes in ask vs guess.

An asker who won't take no for an answer is just an asshole. As is a guesser who continuously hints when they want something and you don't offer.