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Dead or Alive Xtreme [beach vollyball] II.
It's sad because it exists and a team of people made it. It's like if a fedora made its horny posts interactive.
Not sure if it's the saddest, but Memory's Dogma CODE:01 made for quite a ride. You know from the beginning that your best friend is dead, but what comes after can be even worse in some ways.
(Bit of a rough game but still a fun play/readthrough!)
I didn't play the whole game but I remember some of the short stories in Lost Odyssey, which are memories of the main character, who is immortal, were really sad. https://www.youtube.com/playlist?list=PLIrzmchrj04aaB6BYtlnfk9vjXE-mCj4f
Kaim could never say to his daughter,
"You go first to heaven and wait for me: I'll be there before long."Nor would he ever know the joy of reunion with his loved ones.
To live for a thousand years, meant bearing the pain of a thousand years of partings.
From my Nintendo 3DS Game collection probably "Fire Emblem Awakening" Some sad moments inc.
Robin Hood and his merry men.
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