There needs to be some events regarding "rival" special characters if you manage to woo them, my character somehow managed to crush on The Admirer's Admirer and after managing to gift them enough times for them to no longer hate him, she ended up even asking my character on several dates until we got together. I expected some special events out of it, like even changing how some of the DnD sessions go but nothing, even the abrasive comments felt out of place considering at some point we were together. I kind of thought she'd be more showy during the sessions from now on, like she did a few times for The Admirer.
That, and the special characters which you're supposed to woo, there needs to be some negative events as well if you manage to flunk their interactions into dislike enough. For example, and talking about earlier, Admirer getting more desperate if she sees you with someone else, more possessive and so on. I think jealousy, with or without becoming an item, would be really good to make the world feel more alive.
That being said, these two were just the easiest examples that came to mind, other characters could be interesting to have such interactions(Quickieburger advisor/awkward love triangle etc...). Bring out the good in the bad and the bad in the good, if that makes any sense, it would make things really interesting...