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I ended up getting it after trying different things. I think you have to have fun with him, protect him, and share max emerine stones during the trip, but I usually had fun multiple times, so it kept him distracted and he was never happy with the end loot XD

I can't get Dulrig's first heart even when doing everything during the mining trip, what am I doing wrong? What are the requirements? Does he need a certain amount of like?