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I know I'm really late to this thread but I'm posting mine anyway. This was fun to think about.
>Smeargle
I had a childhood dog that I adored. She died in my early teens but maybe if she had been a Pokemon she would have lived longer. ;_; Smeargle also represents my interest in visual art.
>Abomasnow
When I was little my dad planted our first Christmas tree in our yard once we were done with it. Back then it was just about as tall as me but now it's more than three times my height.
>Dustox
I used to play with worms in my backyard all the time, so I'm sure I would have caught a Wurmple. I've always liked Dustox's design and moveset. And with all the moths around my house at night it would have never be lonely.
>Natu
Symbolic of my somewhat recent exploration of spirituality. I also like Natu/Xatu's design as well as birds in general. I was athiest/agnostic growing up and I never considered religion seriously, but due to certain events in my life more recently I've taken an interest in the divine.
>Sawsbuck
I live near a lot of woods (in the midwest) so I see deer in my yard from time to time. I also go for hikes frequently and see a lot of deer then. It would probably be dangerous, but there's no doubt that I would attempt to catch one.
>Wingull
I live right by Lake Erie so catching one of these would be easy. Also a pokebro from my Ruby/Sapphire days and a bird. I think birds are neat.