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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?

(+1)

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