How to unlock this animation?
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On tutorial level of Annie. See if Judy doesn't appear on in next room. You can see it by zooming out near the first gate. If she doesn't spawn then get knocked down by Mason.
For the second one, do Mason quest until he asks you to call Judy or Melanie. Before calling her make Rose do multiple trips. At least 3 times to when you ask her to call Judy or Melanie she will call other girl instead. After that you will see a black haired girl standing next to you. Talk to her, then complete all objectives and talk to her again. This time she will appear on top of the cave.