I believe the new hang out quest (for naomi at least) is just a reminder of side content that you might miss, there isn't anything new for naomi and cait atm, it is just you might not get all the scene in the previous play. For example, to finish the naomi's hang out quest, you need to sit with her at the doorway, with and without giving her whiskey.ZanithOne
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In fact I was expecting the old drunk to get involved in cait's search. Before cait went back to university, she would mention her dreams, including these lines:
cait "And then I met this nice old man who comes to clean the potion making equipment from time to time. He was there, too!"
cait "He was talking to me, although he never really talked to me, just told me I was, um, a clever little lass, he said this one time..."
And if you have met the drunk, she would continue as:
cait "And he said I should visit, and that it shouldn't be too difficult, since, um, he said, I have a mighty steed handy..."
cait "I didn't understand what he meant, but he looked at me like he knows everything and it was so weird!"
Otherwise, she would say:
cait "And he said I should visit, and that it might be difficult, but I have a good teacher..."
cait "I didn't understand what he meant, but he looked at me like he knows everything and it was so weird!"
So this drunk we see is "the nice old man" mentioned by cait.
My personal thoughts about his first encounter is that he is spying on MC, rae, naomi. Rae mentions that they are already exposed upon arrival, so it is natural that the university senses something and wants to investigate. Given the place chosen by Rae, it is probably the most proper disgust.
But the most wield thing here is, what the people in cait's dream would say, depends on what the REAL peason knows and thinks, instead of what cait THINKS he would know and think. So this means people in the house could receive message from outside worlds by just dreaming.
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