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I know im shit at paint so I'll elaborate
GEN 1: I was 5, I would always tie a cape around my neck and pretend to be a super hero at home. I couldn't hardly read and never got very far until yellow came around, and I really liked Pikachu so bam
Gen 2: I was still pretty bad at pokemon and Feraligatr would swipe the rocket base for me and I fell into endless love, Steelix was also so badass I couldnt contain myself and used him in everything
Gen 3: DBZ was huge and I got a ps2 and the budokai games and I was obsessed, I was never a huge enough nerd to wear any attire to school or anything, played through sapphire and my friend had ruby, great times
Gen 4: I wouldn't tell people I still played pokemon, but I bought diamond the day it came out.
Gen 5: later in highschool everyone started talking pokemon again, even the jocks, so it was only natural we all played and spoke about gen 5