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I was having the same issue, and I think I might have figured it out! You need to go talk to Emma in her room, which will point you to explore the area around the apartments (which I've discovered is different than scouting the apartments). Once you do so, when you go to bed that night, the event path you're missing will finally trigger.

Bro thanks so much, that was exactly what I was missing.

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omg thank you so much. i love youuuuuuuuu

I'm glad it helped!