I was replaying because I saw it updated 10 hours ago. I guess that was just the dev log... So stopping my replay to give this bug report which I just managed to reproduce:
Gave out all of Gemma's Cupcakes and went back to her. During that final conversation, there was a spot where Gemma disappeared, right after Gemma said "How's it going?"
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In other things, I thought it there'd be a would be Gemma X Sorrel ship, but given the Wooden Dragon responses, everyone in town can see the real ship! Aww! Cute!