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When I played red/blue back in college I chose charmander because I wanted charizard due to the fact I like dragons.
I never played gen 2 and only got back into playing pokemon when gen IV came out.. however I have a copy of emerald and I picked torchic because I generally prefer fire types to grass and water and I like Blaziken a lot, but swampert is a very very close second.
For platinum I chose chimcharr as I think it's adorably cute and I like the combination of fire/fighting although I feel having it three times in a row is a bit boring I actually do not like gen Vs fire starter tepig at all.
On my copy of HG I chose Totodile for a rather silly reason... my partner at the time picked cyndaquil and named it after me because I love fire types, so he asked me to pick totadile and name it after him because he likes water types.
When I get around to playing my copy of white I'll be picking Oshawatt I like him best out of the three and he's based on one of my fave animals an otter and the samurai who I am also highly interested in.
Gen 1/FR/LG: Bulbasaur or Squirtle (rarely Charmander)
Gen 2/HG/SS: All three
Gen 3: All three
Gen 4: Chimchar or Piplup (rarely Turtwig)
Gen 5: Oshawott (never the other two)
On my very first playthrough of Red, I picked Bulbasaur because I'd heard it has the easiest time against the first two Gym Leaders, but I got very bored about a month later, so I restarted the game to play the adventure again. (I'd never do that now. Still feel kinda bad about deleting my first ever file) Now I'd played the game a bit, I wanted a harder beginning this time around, so I picked Charmander instead, and now I always pick the fire starter in the first playthrough of the Gen, for some reason, and pick the Grass starter in the 3rd game.
Squirtle is the best Pokemon ever. I picked Totodile, but he wasn't nearly as cool. Torchic was alright, but IMO the starters went downhill after the first generation.
Is this gen 5 or every gen. Oh well, I'lllist them all.
Silver: Chikorita
Gold: cyndaquil
These two I chose for the cute factor. I was 12 and thats all I really cared about.
Ruby: Torchic- again cuteness
Emerald Treecko- my favorite Hoenn starter, Ilike grass types alot.
Sapphire- Mudkip cause I liek mudkipz lol.
Diamond- Piplup, mostly cause I watched the anime and that was what Dawn picked.
Soul Silver- Chikorita: Nostalgia reasons mostly, because Chikorita was the first Pokemon I ever chose.
HeartGold: Cyndaquil- Because I was resetting for any shiny starter and that was the one to shine.
Black/White: I chose Snivy in both because I liked it the best.
I usually pick Fire-types, mainly because they're the cutest, but in Diamond I picked Piplup on the most recent playthrough, because I like Steel-types.
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