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how did you not kill him?
i mean, you can make him free her, but then he will get killed by the other girl anyways.
and you'll be forced into a fight with your frined anyways.

did I miss a step?

Or should I have not side tracked and instead went straight for the boss when coming to the intersection for the first time?

super late, but if you just dont help anyone and get all the chests then go fight him then Illi kills him