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i picked chikorita as my starter Pokemon in Pokemon crystal as it looked the cutest of the lot even though it's a grass Pokemon and green i still liked it.When i got Pokemon gold a little while after that i chose Cyndaquil as it was my second favourite for some reason.
I first started with chickorita. My first copy was in japanese, so I didn't knew what I was doing :P.
In my second play (In another catridge) was Totodile, because I thought it would be useful for the first gym.
I chose Chikorita on my Silver game specifically because of the challenge with the first two Gyms, since I chose the easy way out with Bulbasaur with the R/B, so being one for a challenge, I wanted to try it and see how far I could go.