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well from what i know different days of the week/ locations unlock different cut scenes depending on your star lvl so example if you hang out with a guy on a wednesday but then you do other things during the week till next week wednesday and you go hang out with him again it wont work you need to try every Monday-Saturday when ever your relationship status increases with the stars 

I've noticed that. :< Unfortunately even after hanging out with him every day for a month, there's still no event. TwT

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Yea it took toru quite a while to confess to me too sadly only after the fireworks festival and I had him at max heart + almost full stars for weeks before the July holidays. It's either a bug or intentional because of his past and personality. 

If the creators would be so kind to address this issue.

I don't know if their always reading everything but if i do see more issues like this ill try to officially report it. Maybe they are working on it just didn't really tell anyone, could be fixed in the next update.

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It is not really a bug. I'm not sure why people find his route that much harder even though the condition doesn't differ much from the other guys... (I'll try lowering his condition in next build tho).