Hmm, gonna make a little table of sorts.
Gen Version Pokémon Nickname
I | Red | Squirtle | -None-
II | Silver | Chikorita | Taichi
III | Sapphire | Torchic | Clyde
IV | Diamond | Turtwig | Botticelli
Out of these, the only survivor is Clyde the Blaziken, and I'm having mixed feelings about restarting the game. On one hand, I wanted to play it again from the beginning, on the other, I actually caught Latias, and man, it would be an 11 year-old save file I'd be destroying...
I haven't been able keep up with "new" Pokémon games since a long time ago, because I couldn't afford the consoles, and still can't. Now I do have a DS, and was able to get Diamond, but that was already in 2011, 4 years after the game came out, and I haven't been able to get Black yet.
If I do get Black and eventually Y, my first starters will probably be Oshawott and Chespin. Still not sure about their nicknames, though.
P.S.:
HOLY MOLY 500 POSTS! ...Huh. What took me so long?