I've restarted a couple of time so far
Only once, I was able to heal the dying man at the healer's shop and have a conversation about it.
I think you may have to be close enough to him and also maybe have talked to the healer first...maybe even offering that beer...
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If you talk with an Elf to the Elf in the camp near the turtles, only once I was able to tell her that Atusa was dead, all other times i didn't have the option, it kept giving me the conversation about hopes that she'll come and rescue her. I've click on Atusa's corpse, talk to the guy at the entrance, examined the body but the conversation won't appear.
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After a few run in the castle in different games, it is the first time i ever saw the kid that will help me get inside the boat. Although every time i did save the soldier downstairs that gave me the clue to ask for madame whatever to be able to get in the boat... don't know what triggers that....
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If you give the ball to the dogs, you cannot talk to Emmie anymore for Buddie's behalf