Did a video game once made you cry?

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^^^^^ I can't agree with you more. Especially because I'm extremely nostalgic in regards to the Pokemon games, especially the 4th generation ones. Plus the music alone sometimes brings me to tears, especially the Mystery Dungeon games.

Whispered World. Some eyesting. Actually Memoria series was a but twisty to the heart and FF7. I am usually a bad guy so my tragedy is at the start of the game then it is all about dem rivers of blood.

There are quite few games that have backstories that make you go "Nuuuuuu! Don't die for meeee!"
Ill be content rogue over tragic Shepherd any day.

My fiance suggests This War of Mine to make you say Onion Cutting Ninjas are near

Some parts of Mass Effect 3 hit me pretty hard. Mordin and Legion were a couple of my favorite characters in the series.

There were moments during Firewatch that made me choke up a bit. The ending of FFIX made me cry, but I was 12 when I played it. More recently Life Is Strange did too quite a bit near its end.

Beyond two souls hit me extremely hard before the option to choose your ending that reveal tore me apart

Most recently Rime. It was an enchanting, mysterious little game that has a massive emotional bombshell at the end which changes your entire perspective.

Arthur Morgan's last ride in Red Dead Redemption 2, I think that was the only time.

Clannad........................................100% Clannad (and the anime)

I honestly can cry over basically anything. Always been that way. I'll deliberately avoid anything that promises to be sad in any way because I just cant deal with it.

So there's been plenty of games like that.

I can think of one really notable example though: In Illusion of Gaia (also called Illusion of Time) on the NES, the main antagonist is, well, not really a "character", instead it's this thing called the Chaos Comet, I believe. An ancient super-weapon that went berserk, and now persistently flies around, every now and then coming back towards the Earth, mutating creatures into all sorts of monsters and preventing civilization from advancing past a certain point. Your goal in the game is to somehow reach and destroy it.

At one point, you meet up with this thing in some ruins that reveals that the Chaos Comet essentially pushed the world into a sort of incorrect timeline... that this wasnt how things were supposed to go. It shows the characters (and thus the player) the alternate timeline that is supposed to be the correct one. Basically, our timeline IRL. It shows the world, green and vibrant in the game, replaced with the same grey urban mess that I've always found to be bloody depressing in real life. I had already been really bothered by that at the time, as I'd been watching some of my favorite forest preserves get slowly taken over by housing developments and such, and seeing that happen even in the game... and knowing that it was your freaking GOAL to make that occur... just hit too hard for some reason. The fact that the game's story tended to be an overly emotional one from the start didnt help... it already had alot of depressing moments. And indeed, when you do defeat the entity that controls the comet, reality twists itself into the depressing "correct" version, so it's not like that got averted or something.

I really loved that game, but that just bothered me way too much.

Not just that moment though. There's the infamous "pig scene" that it had. Aside from that being horribly sad, I genuinely dont understand how that got past Nintendo's censorship. That one went a bit TOO far. I know I'm far from the only one that got affected by that part.

I played Illusion of Gaia too, though I enjoyed its sequel, Terranigma more. I remember having a similar response to developments to Terranigma, as it had many similar elements. You spend the entire game doing the bidding of your elder by rebuilding the world from a barren wasteland, from the continents, the plantlife, the weather and atmosphere, animals, and eventually resurrecting humanity.

Often bringing about these changes would bring negative changes as well as positive, starting with minor things such as the loss of ability to converse with plants as you introduce more complex species to the world. As the world begins to follow a capitalist economy, you'll help aspiring artists such as Henri Matisse develop their talents, only to see them become burnt out, regretting that they've lost their passion as their success led them to chase money. When you help develop the human towns to develop, you'll see them turn to entertaining themselves by capturing and imprisoning the animal buddies you spent the early game helping, keeping them in zoos or trading them on the black market. Later you set about advancing human civilisation by finding and assisting great people with their labors, helping Alexander Bell to invent the telephone, Thomas Edison to invent the light bulb, Wilbur Wright to invent the aeroplane, and voting for political parties. But then another genius scientist you help has his own idea for human advancement which includes a devastating eugenics plan, and you'll see the effects of the militarisation of technological advancement.

Throughout the game there's this sense as you continue to develop the world that every advance to humanity is in some way detrimental. Other plot developments have the protagonist question whether doing the bidding of your elder unquestioningly was the right decision. The ending is bittersweet; the protagonist saves the world and humanity, but in doing so has lost his childhood friend, his hometown, and everyone who lived there. The people he's saved don't even know they've been saved, and they'll never know of the existence of their saviour. It's an ending left to interpretation with some questions left unanswered, but regardless of the answer you come to it's a tragic one that left an impression on me.

The Mass Effect series has some moments, and Life is Strange came pretty close.

this scene broke me for awhile especially since this was a pretty cruel twist

Undertale, pacifist ending, that was pretty heavy.
Last of Us, the entire ending and a lot of near-the-end dialog with Ellie.
Also Shadow of the Colossus has it for the most heart rip out moment for me at the end. I will only say on the way to the last colossus. That is all.

Telltale's The Walking Dead season one ending tears me up every time.

Joel's daughter in The Last of Us