If Ray was stuck in a Time Loop
Let's say Ray has been spending 10 years trying to save his best friends, only to watch them die in front of his eyes and start the cycle over again.
Ray continues to show signs that he cares and will do anything to stop the same things from happening. He predicts whatever might happen and uses caution.
Each time he figures out what works but not everything is predictable.
He starts getting used to what happens so he can know where Norman and Emma are and act. Norman somehow still manages to outsmart Ray, much to his digress.
Ray could have been pretty optimistic in the beginning until reality hits hard. Then, he starts losing feeling and confidence in himself, after seeing his two friends dying over and over again.
Then, Ray thought he could kill himself in place of Norman and Emma to stop this cycle, only to find that Norman and Emma are both also stuck in the same time cycle. So they've been trying to save each other through the endless time loops until they manage to escape.
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Idea inspired by Kagerou Days and Magica Madoka.