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One time in the GSC days, I named a female Rattata "mommy" a male Rattata "daddy" and took them to the breeding center to nickname a new baby Rattata "junior"
Then there was that time I was obsessed in that series the Baby-Sitters Club and I named all my Pokemon after the girls and their clients. XDDDDDDD Those were the days! Then there was that Zelda Majora's Mask craze. Nuff said.
I once named a Kecleon "Karma." (That's probably not incredibly funny or groan-worthy unless you're into 80's music.)
And to the Douglas Adams fans out there, a Kadabra on one of my games is currently named "Slarti"... which is just short for "Slartibartfast." (I figured Alakazam bears some sort of likeness.)