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I cried when Crystal died. Though, I'm mostly upset with myself for not writing down the stats/nicknames when I got the warning of the game about to die. I'm just so glad I still have access to my 10 year old+ pokemon from Hoenn despite my dislike of RS. They may not be battle worthy like my current pokemon, but they will always be special to me.
I also cried when I lost my original Blue save file as well. However, I was 10 when that happened because I was impatient when my friend was getting Mew for me. I caught all 150 pokemon legit. I just wanted the last one... Stung worse when the real Mew glitch was discovered years later.