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Wanted to add as well that the Milkshake with Misa quest did trigger and completed normally. Got the +1 heart, which put her at max currently available including her 2 gifts. However, it retriggered her conversation where she's angry and it then redid the milkshake scene + MC room scene. 

The second one completed it the same, pop up for the heart and question completion etc. This bugged her name and hearts out in the relation screen, but properly finished the quest. (it's worth noting though that I did just continue my current save. It's possible that due to having already encountered that specific bug it just had a bit of an underlying issue. Not sure how that would play out on a new game.)

I also don't seem to have any Judith content? I realised that each character gets their own gifts, so I already gave the gifts out. She has 2 hearts. I can talk to her but it's just the basic conversation. Is there somewhere specific to get her quests that I'm missing or did giving her the gifts early maybe break things?

Kind of the same with Crystal, she has 1 heart remaining and I've given both gifts but she has nothing to say to me anymore. 

Maybe I need to play more? I never had Lilith come back to talk to me either, unless I'm meant to find her somewhere or it's a certain number of in game days?