Yup, once the BFF is down to try dating, you'll know, it's a whole thing. ;)
More "everyday" type events, reactivity, and socializing is something I'll keep working on. I try to keep a balance between big new content additions and just going back to shore up the foundations, so to speak. Both are important.
I don't think every special NPC will have their own big storyline... some just sort of fill particular niches, or I wanted the player to be able to see at a glance who they are, and that's why they have a listed role in the story. At some point I might have to make some distinction in the UI between NPCs that you can pursue a full storyline with and ones that are more just minor side characters.
Your suggestion would be a bit of work but is possibly something I could build into the existing data structure for events. "Things to do" is meant to be sort of a placeholder until content is more generally findable or tutorialized/introduced in a more immersive way. Moving toward storyline hints would be better for sure, and better address the questions players tend to have.