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For anyone is struggling to find Caleb for the first time,I solved the problem apparently it is in the Full moon event idk if you need to do all the quest but i finished them anyway.After finishing the Full moon (mine is the logan werewolf route so mine last quest is 'talk with logan and ask him how he feel after antilycan treatment')and Caleb part will appear(you need three hearts with Bernard but I only have 1 but it still works)so ya , I hope this helps 🙃(and im sry if i spoiled anything)

Ummm can I ask how  do I encounter Caleb for the first time?(the location),I also finished building the house , the fair and the watch tower if the help. I've searched everywhere for answer but... it was fruitless.Plz someone  help me!