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I: Squirtle (I played Yellow first, but I didn't "choose" Pikachu, so obviously it doesn't count)
II: Totodile
III: Mudkip
IV: Piplup
V: Oshawott
VI: Froakie
...notice a trend?
1998: Blue: Bulbasaur
2000: Gold: Chikorita
2003: Sapphire: Treecko (yeah, I used to think that Grass-types were the easiest thanks to the manual for Blue telling me, I stopped after this point)
2007: Diamond: Piplup
2011: White: Oshawott
2013: Y: Froakie
Kanto: Pikachu (Yellow)/Bulbasaur (Leaf Green)
Johto: Totodile (Never played HGSS)
Hoenn: Mudkip (Probably going to use it again if I get ORAS)
Sinnoh: Chimchar
Unova: Oshawott
Kalos: Fennekin
I usually pick the one I like the most first and then go from there. Also I never reuse starters in a single gen with the exception of Black 2 since there was an extra game.
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