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I think somewhere between Gen 4 and 5. Not because of the lack of quality, infact those games are probably some of the best in the series. It’s just alot of people were going through that “pokemon is for babies, everything needs to be brown and bloom” phase. Another thing I noticed in my friend group is alot of people only bought one of the ds era games and didn’t pick the series back up until X/Y. Infact Almost all of my friends back into pokemon from X/Y and have bought every game sense. But that might also be because we were becoming adults and had jobs that let us afford games more often.
So basically
>gen 1 kids growing out of pokemon
>now as teenagers, they’re insecure about liking pokemon because “for babies” image at the height of the dudebro bloom era
>now as adults they got back into the series and can afford every game now instead of having to rely on their parents
