The first time a game made you cry.

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As a kid, maybe Jak and Daxtar 3 (I got really frustrated at one of those races and/or turret sections).

Shadow of the Colossus made me choke up as a kid too, but I think I refrained from crying outright.

In recent memory, Red Dead Redemption 2 really fucked me up.
 
-Crisis Core's Ending,
-The last human encounter scene in Soma
-Ellie petting the giraffe.
 
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As a kid I think it was Klonoa; Door to Phantomile because of the ending where basically you save the entire dream kingdom and pretty much get a "LOL, cheers for the help, now fuck off back to your own planet and lose all the friends you made along the way".

I can't really think of any times recently, maybe during the big final confrontations of the Persona games when all your Social Links come out and cheer for you in the most weeby anime way possible? Those would be the closest for me.
 
the ending of professor layton and the lost future absolutely shredded me as a young teen. layton realising that the experiment that killed clara actually sent her ten years into the future to the present day and him having to say goodbye again, paired with the music, made me bawl.

undertale's true pacifist ending too
 
Closest would be the ending of Asscreed Black Flag. PC reflecting on losing all friends and comrades in his pursuit of wealth, then the fucking song and him seeing the dead friends, and then leaving the pirate life behind, leaving on a ship with his daughter, knowing how the future turns out for him from asscreed III.
 
Bioshock 2 ending. I will always have a dull ache of pain, even if I don't cry.

FO:NV "Begin Again". I don't know how to express that feeling of standing in that room, the radio talking to you one last time, after spending time at the casino. It's...hauntingly sad. It's always stuck with me. I want a tattoo someday that says Begin Again. I love that message so much
 
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Dead Island; the trailer is beautiful.
Too bad the music was ruined by pretentious faggots who think playing that piano piece makes anything "sad".

Thead tax: I'm surprised I haven't seen any FFXIV posts and while I don't usually tear up at any scenes in games (unless we count Walking Dead) this scene in particular hit me like a truck for some reason.
 
Pokemon Mystery Dungeon 2’s entire last pre-credits section is emotional, but the part right before the credits (your partner visits the beach from the beginning of the game, reflects on everything that happened, and it dawns on them that their best friend is gone for good before they break down crying) really got to me.
 
I was like 8 but Majora's Mask ,right at the very end, when you hear Saria's song. It's not even a sad ending but I bawled.
 
Final Fantasy VII: Crisis Core, because of how heartbreaking it is to not only watch the protagonist die in an unwinnable fight against hordes of enemies, no matter how long you struggle, but also because you watch him progressively "forget" all of the important people you've met throughout the game, be they friend, mentor or love interest, all in one final act of selfless sacrifice in hopes of a better tomorrow not for himself, but for a friend.

There was also the one mission in Metal Gear Solid V: The Phantom Pain, where the game makes you walk into the quarantine platform on Mother Base and put down your own men (some of which you may have played as for side ops). Choosing not to kill them means you either watch them try to exit and get burned alive, or you slowly watch them succumb to their afflictions. The goddamn room where your soldiers are arguing and stop upon seeing you, "Let's let the Boss decide" as they hum the Peace Walker theme. Oh, and the Paz follow-up story. "Peace Day never came." :(

That, and Nier: Automata.
 
Gonna sound like a faggot but To The Moon got me good and I cried a lot. Pretty sure it's the only game that actually managed that feat, no clue why.

To the Moon

I remember being warned before I bought the game, 'its definitely gonna make you cry' to which I thought, nah I'm not a faggot.

7 hours later, ugly crying so hard my vision is blurred and I can barely see the screen to finish the game.

💖
 
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I was like 8 but Majora's Mask ,right at the very end, when you hear Saria's song. It's not even a sad ending but I bawled.
Link started the game with looking for Navi and that's what he's doing after preventing the moon from crashing.

Ffs there's still no conclusion if he ever found her again
 
diablo immortal. not because the game is good or anything but because im in severe debt now and i cant get out because ive already sunk too much into the game to quit please help me
 
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Silent Hill 2 and seeing Angela walk up that flaming staircase + everything else past that point was the first, and by some miracle I went in blind as a bat beyond "wife dead, life bad" even though its twists are common knowledge at this point and I played through the whole series well past release. Harry's death after he'd survived for that long in Silent Hill 3 got to me pretty bad too.

Persona 3, OG NieR + NieR Automata and Rule of Rose are runner-ups. I got into Homeworld off of a friend's recommendation, and he had me start with Deserts of Kharak.
 
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