Thank you for reading and for your thoughts, Jess!

I think that might be a slightly different situation because it doesn't incorporate a request. The concept of Ask vs Guess is entirely premised around how to frame a request, which is when it can get multilayered because of additional concerns about how to ask without trying to impose, or whether even the act of asking is presumptuous etc.

Without further context, the particular situation you describe is more pure unsolicited presumption, which understandably would annoy anyone!

However, you're not wrong in saying that a Guesser 'guessing wrong' (ie trying to veil their true intentions based on how they think (inaccurately) how the other person will react) can have disastrous reactions. That can certainly be true and also insulting as well!