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How do you go about giving your OCs Pokémon personalities?
Honestly I kinda take cues from the Pokemon anime. I try to give them some sort of quirk while also considering what sort of role they'd have in the team emotionally. I also consider what their battle style is like and try to factor in what sort of temperament would lend itself to that sort of style...
Really, I just treat the Pokemon as if they are OCs themselves. They are, after all.
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