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My charmander into charmeleon. This was back in the days I thought a master ball could catch anything. So i used it on a trainers pokemon. I also ( without knowing ), done a solo run with my charmander ( and failed ) coz i couldnt be assed to train anything else
My first evolution was on my brothers pokemon red in 1998, when he let me have a go at it, and then raged at me, because he was trying to train his Charmeleon to learn flamethrower before evolving it, but I evolved it and it learned flamethrower anyway.
So my first ever evolution was a Charmeleon->Charizard.
Most likely Caterpie -> Metapod or Squirtle -> Wartortle on my original Blue version. I actually can't remember what my team was outside of my starter on my original Blue playthrough, but it seems likely that I would have caught a Caterpie near the beginning.
I think mine was probably Nidoran -> Nidorino.
The first game I bought was Yellow, so no evolving the starter there anytime soon.
I never did evolve that pikachu, it seemed to important, following me around and all :)
I freaked out when my Torchic evolved back in Sapphire, then learned the "overpowered" Double Kick. I thought it was the best move ever. Cuz it hit twice ! :-x
I freaked out even more when it evolved into Blaziken. And learned Blaze Kick, which replaced Ember. Haha, good times !