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Title says it all, what was your saddest experience with a video game?
The ending to Witch's House made me wish I hadn't solved all those puzzles or won those chase sequences, it was just so heart breaking.
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If I do recall correctly, there may be a similar topic on this. It's here, but I may be mistaken.

But as for me, the ending of Pokemon Mystery Dungeon 2. The game is so good with allowing you to have an emotional bond with your character, and it all goes when you find out that you can't exist anymore. The ending nearly made me tear up. As well as this, I also nearly teared up during the credits of Ocarina of Time 3D: Master Quest, and this is partly because I'd fully completed the game and now had nothing left to do with it aside from restart.

Every time Mario beats one of koopalings or bowser.

Could you please put spoilers over these things? Especially since y'all are mainly mentioning deaths of important characters or game endings.

Undertale
Neutral and Pacifist run, on the ending

Genocide run, on the entire game.

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Mother 1/2/3
Know the entire story about the series, know that you killed Giygas that was once a big friend of a old ancestral of your family, and that Pokey also died on Mother 3, as long with Lucas' Mom.

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Donkey Kong 64
Know that Wrinkly is Dead

YellowMe wrote:

Spoiler: show

In Beyond Two Souls, when Nathan's daughter and wife die in a car crash. He was such a nice and caring character. I was heartbroken when it happened.

I'd have to say

TLoU Spoiler: and some of Silent Hill: Shattered Memories' endings.

AeroMatter wrote:

YellowMe wrote:

Spoiler: show

In Beyond Two Souls, when Nathan's daughter and wife die in a car crash. He was such a nice and caring character. I was heartbroken when it happened.

Spoiler: show

It wasn't even that sad because you literally never hear of Nathan's family so when you think about it for 2 seconds it becomes kind of cheap emotional tricks (which 95% of that game is). I can't think of a single sad moment in that game that's genuinely sad.

YellowMe wrote:

Spoiler: show

I know, I'm a softy. But you gotta admit, the music and the way it's played out is well done. That is the real reason it made my eyes tear up.

At some point OoT's ending made me a little tearie, overall seeing Mido and King Zora sitting there after realizing they won't see Saria and Ruto anymore since their job as Sages prevents them from doing so (even though in the same moment they just pass right above them and do nothing but stare at the horizon from Death Mountain).

Jumping to Shadow of the Colossus, man what a fantastic game. The Witch's House's endings also made me cry, more so than any other video-game for sure. The game itself doesn't have any story development whatsoever, but the ending up to this day in my opinion holds one of the most, if not the most, plot twists I have ever seen.

The hole Mother 3 is pretty depressing compared to it's prequel and the same goes for it's ending... It's pretty hard to describe it without talking about it's plot. I'll try it: Wind Waker's and Super Paper Merio's endings were also pretty deep... somehow.

It's a relatively old game but I guess I'll just put in a spoiler box anyways.

The saddest moment I've had is that when in Paper Mario: Sticker Star, Kersti sacrifices her Powers to Mario and gets squished to death... I almost cried when I saw that...

The ending of Pokémon Black & White was the most emotional I've ever gotten over an ending. I found it so well written and sad with N's final monologue.

Chrono Trigger. And I'm talking about the actual soundtrack - it has a mystery and sad feel to me, especially this one theme: https://www.youtube.com/watch?v=i_yYFWx8-Mk

Since Linik not only linked to the previous thread but also mentioned Pokemon Mystery Dungeon 2, I'm going to repost the part of that game that made me sad (I played the Explorers of Sky version):

Looking back at Ib,

PixelPest wrote:The ending of Pokémon Black & White was the most emotional I've ever gotten over an ending. I found it so well written and sad with N's final monologue.

Yeah BW had a surprisingly good plot. Definitely appreciated that. Generation 5 was really good in general.

My top 2: