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In Pearl, I chose Turtwig. Later bred it, and now use a lv. 100 shiny Torterra.
In SS, which I play most now, I chose Totodile. Used it until it was lv. 46, then locked it away in a box.
Chimchar because he looks cute and i absolutely love Infernape's design. Plus i love the Fire/Fighting combo and i didn't mind them using itr twice (Yes, Tepig was too much...).
Totodile because he is such a hilarious and hyper-active pokemon, plus i love how he is inspired by a crocodile/alligator.
in my first ever game which was pearl i chose turtwig because my other two friends chose piplup and chimchar and i wanted to be different than them and also turtwig was adorable. also torterra is one of my favorite pokemon. i chose piplup in platinum because i wanted to try something different. in heartgold i chose chikorita because it was very cute and again i wanted to be different. also i already chose cyndaquil in crystal :D
Sinnoh: Chimchar definetely. I must have a fire type pokémon in my team.
Jotho: Totodile. Cause I always catch a Growlithe ^^.
That kinda happens always when I play gen II games.
Although my best gen II game (crystal) was with Cyndaquil as starter.
Cyndaquill in HG/SS and Turtwig in Platinum :) But next time I play Platinum I'll choose chimchar. Torterra wasn't bad, but I wanna to make a full IV Gen team and it lacks fire-types pokémon :s
I chose Chimchar in Diamond (my friend told me to, I was young and didn't understand much about Pokemon, and I thought Chimchar was adorable :3), and then in Platinum I went with Turtwig (back then I followed along with Marilland - I basically made my team EXACTLY like his :/)..then I tried SoulSilver and used Totodile. After that, I replayed Platinum and used Piplup.
Haha, yeh I'm definitely going with either Piplup or (preferably) Totodile to suit a mono-Water themed team. :3 Water-type starters appeal to me a whole more than the others purely because each one so far is distinct and interesting! (though not saying that the other starters are diverse):)