Trying to understand another person through imagining what it is like to be that person leads to profoundly misunderstanding them. You are most likely projecting your preconceptions or are imagining that they are the person you want them to be.
Asking someone to honestly describe their thoughts and feelings in real time in a shared space may lead to some genuine insights into who they are. Not guaranteed, but at least there is a fighting chance you could learn something.
But you must be willing to put aside what you think you know and listen.
Anyone out there trying to build a relationship of any kind with another person please take note.