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For nicknames, I just go with whatever seems to fit their type and "character/personality".
I've got six teams worth of nicknames I could list for you, but to save time and typing, I'll just do it for my current Y team.
>Chester: A play on the name "Chespin" and "Chesnaught".
>Curly: Honestly, I don't remember how I came up with this one. I had a reason, but I forget it. Maybe something to do with Squirtle's curly tail?
>Roxie: Named after the Poison-type gym leader from BW2. Also, it sounded like a nice name for her.
>Tiny: Because she's the smallest member of my team.
>Edmund: Named after Sir Edmund Hillary, the first man to climb Mt. Everest.
>Ohmassacre: Named after the French name for Eelektross. It's a pretty badass name (even if it's a shameless pun), so I went with it. I was also tempted to go with his German name, "Zapplarang".