This reminded me of a game of chess against yourself, but not knowing the direct outcome anyway. Do you get "Oh, if only we could start things over..." for all endings. It was nice having this conversation, not sure why he has to go. :)
"We don't see things as they are, we see them as we are." This was the theme for the 14ᵗʰ GGJ, and Our Way is our humble game for it.
You always hear what you want. In a rare conversation where you not only control what you say but also what you hear, would it be easier to have things go your way? At least in a game you can start things over, experiment. Our Way is an experiment on the fact that everything said to you is subjected to your own interpretation. Conscious or subconsciously.