Has a bad ending ever managed to make you feel bad, guilty, disappointed in yourself, even just mildly? If so...

Persona 5 until I realized I hadn't gotten the bad ending that's just how the story progresses.

I intentionally got the first bad ending to check it out and then I realized the same thing visually happens either way

>Furry catgirl is a nice person and has sincere care for her best friend, devoting her life to her
>Storyline revolves about her friend aging rapidly because she used up all of her spirit to save a demon she loved when she was younger
>Demon is going around literally fucking up shit to save granny-friend
>At the same time, third-wheel friend - who is in love with the granny and hates demons - joins your party, letting you know that demons more often than not don't know feelings, and in reality imitate them to trick people to love them

>come to a crossroads by the end of the storyline where furry and third-wheel bump heads on how to save granny-friend after she is kidnapped;
>Furry is being stupid about her points, so side with third-wheel, since at the moment he makes the most sense, and inevitably the demon needs to be put down
>FUCKING KILL FURRY-FRIEND
>SHE GETS SENT TO HELL
>FORGOTTEN FOREVER

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Dear Pesky Plumbers,
The immigrants and I have taken over the Commonwealth. The Queen is now a permanent resident in one of my seven Muslim Mosques. I dare you to find her if you can!

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Some isekai VN
In short, the bad end is he remembers some deep childhood trauma which kind of unlocks his emotions, basically opening a long lost stab wound, then you immediately get thrown back to your world, and he breaks thinking anyone he will ever consider important will leave him. The only thing he can think to do is kill a person who wronged him and then himself.
Made me feel pretty bad.
Also felt bad just playing the Toma route of Amnesia Memories since I had to keep asking myself what the fuck am I reading.

The Ending of Skyward Sword because it somehow sours the entire series.

most VN bad endings have shit writing and have the characters just do random shit that doesn't make any sense and doesn't suit their character so that the MC can die and they can wrap up the story path. I wish they just woudln't bother making story paths if they were going to half ass it but I see it all the time.

Fallout 4, why did I even bother

That one in particular was pretty in character, but I know what you mean. In the same VN there's a bad ending where everyone pretty much just fights each other for the rest of their lives and it was weird.

Detective Pikachu. I was disappointed in myself for wasting my time in that game for Mewtwo to say "you will one day find your dad. Bye". I didn't pay for the game thank God. But what a shit ending. It was inferred Pikachu was his dad but nothing was concluded.

Not really a bad ending but Home alone, getting a game over showed you tied up in a mailsack getting shipped off in a subway. It actually made me uncomfortable as a kid

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Learning that the bad ending in shadow hearts was canon was a real downer

Fire Emblem Conquest. It was Ironman, so no resets to save people.
Laslow and his daughter Soleil's support conversations were about how they were afraid to lose each other, and promising to both survive for each other's sake. Going into the final battle, I finally got them to max support rank.
In the final battle, I lost Soleil.
I've never been that upset about a dead unit in the epilogue before.

Some of the things you can do in Planescape Torment if you play as evil are pretty rough. I can't bring myself to sell Dakkon off into slavery again or leave Mort in the skull pile.

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And this is the only ending you can get?