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I do have some experience with birdkeeping so it would make sense to me to acquire an ubiquitous bird pokemon, ideally Starly or Fletchling but would depend on my starting region.
If I were in the pokemon world, I would strongly desire to befriend a Gastly as they are very intelligent and prefer to roam about at night, I would love to wonder about existence with it and make jokes, I think we'd get along well, they can be found in urban areas at night so it should be doable with some effort.
Clefairy and Cleffa are known to be sold, I would like to think I'd either receive one as a present or be able to afford it at some point, it would make a real bro and I've liked it since the first games. I'll make my bird a Pidgey since we're going with a Kanto theme.
These three would probably be my bros into adolescence and teenage years. Or the first three I'd aim to befriend if I was thrown as an adult.
I'm good at games but not great with competition so the others would depend on whether I do good at battling and start a gym leader challenge/pokemon journey. If I did, I would consciously try to make a balanced team depending on what pokemon I stumble upon in my adventures, train my bros to evolve and acquire the items they need to do so and even look for a pidgeot mega stone eventually. If it doesn't work out I wouldn't care because I'd still get to enjoy my bros' company and maybe befriend some others along the way.
