The person who expects you to know everything has mistaken familiarity for mind reading.

Long familiarity gives you good guesses, not access. Someone who knows you well can predict which restaurant you would pick and still have no idea that today you wanted to be asked. The trouble starts when closeness gets treated as a substitute for saying things: the unspoken expectation goes unmet, the disappointment is real, and it lands as evidence of not caring rather than of not knowing.

Say the thing you were hoping would be guessed, even though saying it feels like it spoils the gesture. If you are on the other side, ask instead of predicting, especially about the things you are sure of.