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I've gotten every gloryhole character except the bottom one on the left hand side, the "journey of a pink dragon" one. Is there something specific I have to do? Or interact with a certain NPC to unlock them? Or do I just keep spamming gloryhole until I get them? thanks in advance.

You need to talk to a pink dragon a few times. Places he is are Safen -> Gloomy Forest Club --> Beach --> Safen glory hole when the number is 4

Thanks a bunch! I totally missed this dude