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My sister and I have been playing since red. She loved the crap out of water types, while I had some kind of obsession with speed (a team full of the fastest Pokemon--Jolteon, Aerodactyl, etc). So, whenever I see a Vaporeon or a Jolteon, I always think of my sister.
On that note, not a Pokemon, but Gen 3 has always had a special place for us. Hear me out. My birthstone is Ruby, and my sister's is Sapphire. My brother was finally competent enough to play and spent a lot of time stealing our games. Third version announced. It's his birthstone, Emerald. We got him an SP and the game, and that was that. We are a lot closer than other siblings tend to be, and I think it's because of our mutual obsession with gaming and Pokemon in particular.