For me it was the Telltale Games Walking Dead franchise, I cried throughout the entire series and especially bawled when I finally finished. Also Ori and the Blind Forest, SOMA, Nameless ~ The one thing you must recall ~, Everybody’s Gone to The Rapture, Life is Strange 1 & 2, Fable 3. I just get invested, okay?
I haven’t cried much when playing COG or HG, I guess because I feel like I brought it on myself when I screw up an option.
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Think this must have been mentioned so many times in this thread already but the Mass Effect series, Mass Effect 3 particularly. I think it’s just how invested I became in the universe and and the characters over the course of three games. I loved the entire crew of the Normandy and their character arcs, and losing them hurt Mordin’s death in the third game hurt especially, I remember crying then but the ending really got me the crew saying goodbye to Shepard before the final assault, getting invested and getting to know the characters meant it felt like it was saying goodbye to friends in a way, then Shepard sacrificing themselves to defeat/control the reapers, with their love interest placing their name up on the memorial The music was spot on too, music is definitely key in games like that and I feel they really hit it out of the park. It left me a mess at the end but I still wish I could play it all again from the start fresh.
Another choice I thought about might sound a little odd but I thought I’d mention it, Stardew Valley. The farmer’s grandfather giving them the deed to the farm along with the talk he has with them, that got to me. The villagers in Pellican Town where the farmer moves to are worth mentioning, all of them are great but some have very human problems and flaws that really caught me off guard, Shane probably being the best example, it’s a great game that has a surprising amount of depth under its seemingly cheery surface.
Just my thoughts, sorry it seems like I wrote an essay.
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It still irks me that the servers went down, so I can’t get the required Military Efficiency (I think that’s what it’s called, not sure) to get the ending where Shepard survives.
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Mass Effect series are my favorite, also Dragon age series. (I’m a fan of Bioware games in some sort) It’s been a long while since I finished the third part of the Mass Affect series, I miss Gareth tbh. Wasn’t Shepard to be dead anyways at the end of the game? There was a mod made by someone who kind of extended the game and made Shepard live, but otherwise Shepard dies. I always thought that the game was supposed to end this way.
Talking about the saddest games, for me those will be a game named IB and a WIP by @Lycoris named Nothing Left to Burn, the second one really played on my heart strings, to the point that I was crying out of pain and sadness. Big thanks for all of the authors and people who work on making such a great content for everybody 
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I completely understand you because I get invested in game characters too and then end up crying and laughing and feeling other emotions as if I have always been there alongside them. The Walking Dead series were fairly sad too, especially in part one and two. When characters die it’s always sad 
. It’s the most painful when your favorite character dies, sometimes to the point where I don’t want to play the game anymore.
I just finished Assassin Creed Black Flag for the first time several nights ago on Switch and it absolutely DESTROYED me. Stede Bonnet’s offscreen death after his final scene where he yells at Edward while sailing away from him, telling how grateful Stede was to have Edward’s friendship. Thatch’s last stand while Edward looks on and is helpless to help his father figure. Mary’s tragic death and last words urging Edward to atone with the Assassins. And the ending scene where Edward overlooks the cove and sees all of his dead friends (some of that he killed himself) while Anne is singing a very sad song then it was revealed that Edward had a daughter that he never knew about, leading up to the credit scene where Edward expresses his regret on not being around for the mother and the daughter.
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Can’t recall the saddest but recently oddly enough it’s an mmo. Ff14 shadowbringers. Ryne, emet-selch, crystal exarch… so many sad moments ;-;
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The House of Fata Morgana - Tore me apart, made me laugh, cry and feel despair. Best visual novel that I read.
For Mother Matron - I couldn’t even finish the rest of the endings because of how it effected and triggered my depression even further. [details=“Summary”] It doesn’t matter what you do to save the boys that are with you, because they die with you. Your mother had been murdered after you were born and you were taken to an island where “mother” basically devours her acquired children and they don’t exactly have a choice because all the children are brainwashed. No matter what you do, it’s hopeless.
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