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My first encounters are:
Red
Gold
Sapphire
FireRed
Diamond
White
X
AS
I had Red on an atomic purple GBC. I must've lost it or something (I still have the GBC). Brother's friend gave me his Red. Traded it for friend's SMB Deluxe. High school friend gave me his Red. Profit?
I have Silver because I don't know. I never bought Gold, but I think a friend gave me one. I must've lost Gold then somehow ended up with a Silver cart that doesn't even start. No profit. I might purchase a Gold cart to keep consistent.
I bought Ruby in response to playing a friend's Sapphire for a couple weeks This is YEARS after playing Red; I skipped second gen and played Gold after being hooked back in third gen. I never owned Sapphire. I might purchase a Sapphire the for same reason above.
After being hooked back in third gen, I bought FR, Emerald, then LG just for kicks. Then D/Pt/HG/W/W2/X.
I bought AS because Sapphire was what sunk its teeth in me. I might as well purchase OR and Pearl too, just to complete the collection. Sinnoh was fucking awesome, so let's do it.