Definitely The Grim and I, It made me happy and sad at the end. The moment I stopped playing it, I realized that even though I am composed of atoms, I still don’t matter.
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Thats the way it is broke me during rdr2
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I can feel the heartbreak and longing from the trailer already. Definitely gonna check it out, thanks 
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Got a lot of recommendations for RDR2 and now I want Christmas to come even faster haha, thank you all
Final Fantasy XV. I managed to completely avoid spoilers since it came out, until I played it a couple months ago. I waited until all the DLC were released and all the patching was done(sadly the next batch of story DLCs were cancelled). And just… wow. 210-ish hours to finish doing everything the game has to offer in every aspect, and I can safely say that it is one of my favorite games of all time. But I also kind of hate it. The story is exactly what you are looking for… and that’s all I can say without spoiling tbh.
So if you haven’t played it, I would recommend it wholeheartedly. Just realize you’ll be in for a long one, unless you want to rush it ofc.
I think you can get it on steam for like $40-50 with all dlc included.
As for a CoG/HG, it would have to be as many others have mentioned, Grim and I, with love being your focus… possibly also Samurai of Hyuga series. However it is yet to be concluded, so can’t say if it will have a bitter-sweet ending. But it certainly has those moments.
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‘The Grim and I’ and ‘Creatures Such As We’.
The latter because eventhough the hopefulness of it all the ending just felt so…lonely. It reminded me of al the friends I’ve had and lost.
For other games…I guess I should nominate ‘Dragon Age: Origins’. I’ve only finished the first game in the series and some of the cutscenes combined with the music are quite emotional. Like, I just finished the Return to Ostagar DLC and I’m not okay 
I also want to mention ‘My Child: Lebensborn’. It’s a mobile game and in it you’re the adoptive parent for a German boy or girl after WW II. It punched me in the heart multiple times.
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Creatures such as we grim and I and rent a vice
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Hmm, so far, when it comes to CoG, I can’t say I remember them being particularly sad - though admittedly, I’ve yet to play The Grim and I that seems to draw a consensus here. There certainly are sad moments here and there, but nothing that I would qualify as soul-crushing.
When it comes to classic video games… I can second Life is Strange (I think Before the Storm was even worse than the OG) and The Last of Us. I’d also add to the list Nier Automata (route C is just the worst), and since a few FF games have been mentioned, to me the saddest one would be Final Fantasy X which is almost the textbook example of bittersweet (with an emphasis on bitter).
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While not a necessarily sad story, the death of a certain RO in Fatehaven really killed me. What had me bawling my eyes out was the fact that regardless of your feelings, the character had romantic feelings for the MC, and at the time of their(the RO) death theydimply brushed off being hurt, so as to not worry the MC.
On a related note, Samurai of Hyuga can get really sad, if you overthink things. That story can be so soosososo angsty if only you give it the chance. I think waaay too much about each individual character and that alone makes me depressed for days on end.
Haha also Academy for Future Villians, same thing as Fatehaven; it’s not a sad story in the least, it’s actually very lighthearted and fun, but there’s a certain RO that “dies”(?) regardless and there’s nothing and I mean NOTHING you can do to save them, and I grew much too attached to these characters to simply accept that, so I end up locking myself in my house for a few days to cry out my feelings.
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Way Walkers: University, a friend zone simulator.
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Why did you remind me of that… I cri evrytym.
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too many to count, any game where the MC dies, a child dies a horrible death, or animals are hurt or killed in, usually make me sad
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Alicemare. you just can’t win. and the author wrote a short novel about it for some extra sadness!
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Beyond two souls had me crying my eyes out.
But actually, something that makes me cry every single time is one scene of WoW. In the Legion expansion, when you have to kill Ysera because she has been corrupted by fucking piece of shit Dorius (yes I hate him). When Ysera cries at the moon, and Elune (goddess) answers, carrying her soul to the night sky, making Ysera a constellation under her, ugh, just thinking about it makes a knot on my throat.
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I don’t know if it is just me but I feel having an emotional story or at least a part that pulls at your heart-strings makes it memorable and worth the read.
I will just list the Stories where I was I was a mess of emotions.
Fallen Hero: Rebirth
The whole ride through was a rollercoaster of emotions. The flashbacks and choices did NOT save me. I went with the Ortega Route. It is as @Camille622 said, the MC has the option of loving Ortega but no matter what, is unable to tell them their feelings because ultimately they are not human/diminished and do not deem themselves worthy to be with a human The can only love the RO from afar. Although the concept of the puppet was also a big OOF, I’m sure there are some of us that think life would be different, easier if we looked a certain way or looked like someone else. 
Study of Steampunk: Choice by Gaslight
One word: Finch.
You all covered the rest.
The Eagle’s Heir
Similar to Fallen Hero in a sense but less intense yet still makes me cry.
You have the option of romancing the heir whilst you’re just of lower status.
You can either protect him at all cost or not but the content is well written although I found the ending a bit ‘meh’.
The Harbinger’s head
a Bittersweet death.
Here are some promising WIPs for that sad soul.
Son of Satan: Mortal Coil by Dae-kalina
Ramiel ANGST. Nuff said.
'Til death do us part by will
Oh the feels I get with this one…I’m so lonely. They all leave me
Model Citizens: Unmasked by RenaB
There is the option for the MC to cling to their old wedding ring and feel stuff.
Considering I read this right after I read Fallen Hero …. feels.
and finally of course
Fallen Hero: Retribution by malinryden
for obvious previously stated reasons.
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Well, I don’t know about anyone else, but I cried at the giraffe scene in The Last of Us. I know it’s not an ending, but that scene was just so much to take in after what David almost did to her. It was just so tender and sweet. I didn’t cry at the ending of the game, but man was I absolutely floored when Joel lied straight to Ellie’s face about the Fireflies. That ending still gives me chills.
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The 2 text based games that have messed me up the most are probably the Samurai of Hyuga series. I’ve cried several times through the series as a whole and the end of three wrecked me. The other one that jumps to mind right away is The Ghost of You on steam.
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Telltale Games The Walking Dead: Season One was the saddest ending for me. My nephew and I were playing and I couldn’t handle the ending, so tears just started to come out of me. I looked at my nephew to see if he was crying as well - he wasn’t, but I knew he was trying not to cry. Thinking about it now is making me sad.
I’m glad I played The Walking Dead with my nephew because it led me to Interactive Fiction in the first place.
Because I keep seeing Samurai of Hyuga a lot, I’m going to give it a try.
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Choice of Vampire 1 and 2 waiting for 3 has made me cry for years now
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The Grim and I has been the most emotional COG for me… Doesn’t matter how many times I play it, I still cry.
Props to Thom for being such a great writer.
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