This is the point - you are not skipping anything. As of now chances to get a really meaningful dialogues on that particular subject in any game (probably including dating sims, though could not say for sure) are even less than developing a mechanical system. I am talking only about existing trends, where the number of options is already in place, but the system to handle it still did not emerge.

But it sounds as we are discussing something probable. Most likely neither wish will ever be fulfilled.