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I leveled Lily and Becca in the same day (6 and 5 respectively) and I didn't get Lily's event either the next day or the day after.

Hey there! Which Lily event are you talking about? She has an event at stage 4 (if Becca is also stage 4), 5, 7, and 8, but none for stage 6

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Ah, I wasn't aware there was no event at that point given the relative consistency at which I've been seeing events pop up for characters. Nothing's wrong then!

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Sorry for the inconsistency then! One of the things I want to add to the Housemates menu is a way to track events, specifically for issues like this. I don't know when I'll be able to get something like that added, but it'll be in the next few updates for sure