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My best friend played back in the days of R/B/Y, but he eventually quit by the time G/S/C came out because he couldn't beat me. He's really competitive and quits things if he can't easily master it.
My brother played up until R/S/E. It was always fun to have random battles with him, but by the time the 3rd gen rolled about, he thought Pokemon was gay.
My cousin who lives in a different state was pretty big into X/Y, but quit by the time ORAS came out.
My girlfriend (now wife) played FR/LG a lot, and even played through Platinum and Sun. However, she's casual as shit, and refuses to ever battle me because I beat the shit out of her 3rd gen team over 10 years ago. She says I take the game too seriously and it's not fun playing against me.
She's probably right, since my cousin has said the same thing several times...
