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I have a small anime theory but it needs some work, basically the changes in ash’s character can be explained like this, what we see in the anime is ash through the eyes of each girl, well at least for unova kalos and alola,
>iris constantly tells ash “you are such a kid”: unova ash is immature compared to other seasons
>serena has a crush on ash: Ash goes full shonen protag
>lillie is a girl who feared touching pokemon: Alola ash is one with nature and all of alola, capable of becoming friends with legends like the tapus and solgaleo
While those 3 exaggerate ash’s qualities misty and dawn come closer to what a true ash would be like and i haven’t seen enough of the hoenn anime to say something about may
