Hello! I have a strange question. Do characters have to be consciously aiming to fill out a square for it to count, or can it also be like a "oh this happened and now the square is marked" type of deal?

And more specifically, for the "ideal date" square--do the characters have to be aware that they are on their ideal date? Is there a "right answer" to their ideal date that the character might not be able to put into words (ie could they keep going on dates and not know why it never fills)? sorry if these questions are incoherent