Elite Beat Agents has this Christmas themed comic about a girl waiting for her father to come home, played to a version av "Your the inspiration". That first playthrough of it had me tearing up, probably the only time ever from a video game, and it is a bloody music game?!
A few moments from Zelda Skyward Sword stuck out as emotional for me. That time when Impa turns around and tell Link that he is to late, that one hit my gut. Also pretty much all character development moment involving Groose, bully turns buddy is a story trope I often like.
Meeting trainer Red on top of the mountain in Silver/Gold/Crystal. Pure gaming magic and probably a core gaming memory for anyone who grew up playng the first few generations of Pokémon. It does not strike as sad the same way other emotional moments does, but it certainly make the game world feel real in a sense that is very emotional.
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