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Haha, Pokemon's target demographic is 6-12 years old, I think in terms of boys using male and girls using female Pokemon, it's easiest to understand for a younger mind.
That, and there are so many trainers who don't adhere to that little rule.
Also, about the girls using cute and guys using cool Pokemon thing, that reminded me of the biker with a Cleffa. But it also reminded me that the NPCs are still stereotypes and they're using Pokemon they'd be using to fit the stereotypes, which isn't always indicative of a Pokemon someone would like either.
I mean just like at B2/W2 when all the punk rockers in the beginning of the game used Poison type Pokemon like Koffing. That's because it fit the appearance and stereotype of them.
Just my opinion though, and I'm tired so I can't really fully flesh it out
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