[This post contains spoilers for Magical Diary, Hatoful Boyfriend, Diabolik Lovers, and Dragon Age: Inquisition, especially the Trespasser DLC.]
I don't know if this is a conditioned masochistic response because I always get them on my first try, but I've started really liking drawn-out "bad" endings in visual novels and dating sims. Maybe it's because writers don't feel pressured to wrap everything up in a neat, uniform package with a happily ever after bow on top. Things can be messy. They don't even have to be romantic. I've never understood the appeal of watching sad movies, but maybe it's like this?
(By the way, I'm not talking about the type of bad ends where you choose to go into the left door instead of the right one and are promptly eaten by a grue and returned to the title screen. If you're going to make the player fail for arbitrary choices, at least make the outcome interesting.)
Corpse Party, while a hot mess of a thing in general, has a neat approach to bad endings. There are tons of them, and most of them reveal new information about the surrounding mystery or details about the characters. There are still a few obnoxious "you got caught by a ghost, here's several paragraphs describing your gory demise before being booted back to the main menu" endings, but not many. Corpse Party is a horror game, so it can really lean into bad endings as hard as it wants. The sequel, Book of Shadows, encourages you to see all of them - you can't unlock the game's final chapter unless you do. Book of Shadows itself is actually a parallel universe story that branches off one of the first game's bad endings instead of the "canonical" ending, which I think is so cool!
Most of my favorite dating sim routes are ones people consider "bad", but are rarely labeled by the game itself as a "bad end". Magical Diary, a wonderful dating sim by Hanako Games, has one of my absolute favorite routes ever. It doesn't end with a happily ever after - it's not about giving you your perfect romance. It tells a chilling story about someone falling deeper and deeper into a toxic relationship, and it is soul-crushing and well-written in a way that makes me want to grab my face and go "AARHGHGH IT'S SO GOOOOD" whenever I talk about it to friends. And while the route is unmistakably, definitively Bad - I appreciate that the game makes no point to romanticize a clearly unhealthy relationship - I also like that the game doesn't shove "YOU GOT THE BAD ENDING" into your face.
This makes it feel more like… a story, I guess, but that sounds strange. It makes things feel distant from the player in a way that I find helpful, especially when the story you're telling is dark. Do you want this to be a horror story? Do you want to read a fairytale romance? You can decide that for yourself. These awful things aren't happening to you, even if you put in your name for the main character and you made all the choices you might. The character isn't you, and those choices aren't really yours. They are tools you and the writer are using, together, to tell the story you feel like hearing today.
Another fucked up route I love is Shuu's from Hatoful Boyfriend. It takes the idea of writer and player working together even further. Shuu's route is a horror story, and it makes this clear from the first time you meet him. Yeah, let's keep visiting the scary doctor with the uncomfortable laugh while students continue to go missing! There's no way this will turn out badly!
Spoilers: the route ends with you being vivisected by a partridge. Shuu begins talking directly to the player. "You could tell from the start that I was dangerous, couldn't you? And yet you came to see me, again and again. [...] You knew I planned to kill you, and yet you came anyway. [...] You have chased after death's allure most diligently." It's an incredibly well done, frightening horror story wrapped in a dating sim package, being told with a cast of birds. Hatoful Boyfriend plays with genre and expectations a lot, but Shuu (and Anghel) especially made a huge impression on me.
There are whole games that operate on this premise, of telling stories about toxic relationships. Diabolik Lovers is the one of the most notable - it's a Japanese series of visual novels aimed at women about dating horrible, horrible vampire boys. The men in Diabolik Lovers are frightening to a degree that almost feels comical sometimes? In the first episode of the anime, one of the boys tosses the protagonist (who can't swim, because she's an anime protagonist) into a pool and then deadpans, "Now tell me I'm the best." They are not good dudes. The closest you can get to a traditional happily ever after is becoming someone's blood thrall and/or getting married, and they still treat you like a huge jerk! In one of the endings my awful vampire boyfriend got jealous of his brothers, so I killed them all and burned their bodies so he would be happy! There is nothing healthy to be found here!
And yet Diabolik Lovers has a huge fanbase. Right now, there are five games, two seasons of an anime, and a stage play adaptation. I yelled with delight when I saw one of my best friends had imported me a copy of one of the games for my birthday. I've survived abusive relationships in real life and been through trauma, and I still find myself enthralled by these fucked up, sexy games about fucked up, sexy relationships. I'm not even going to pretend that enjoying these is actually, somehow, secretly feminist and empowering, or even that it helps me cope (although I'm sure they can be that for other people). But I hate that I feel pressure to disclose that in order to talk about this, because maybe I don't want to loudly announce the very vulnerable parts of myself to others when I just want to talk about my fantasy vampire boyfriends. I'm not eating directly from a dumpster because it's subversive - I just really like the taste of garbage.
Don't get me wrong, I still love fluffy fairytale romances, too. I think I've completed Dragon Age: Origins around eight times now, and I can't bring myself to do anything but marry my adorable darling Alistair and become King and Queen together. Iron Bull's route in Dragon Age: Inquisition, sexual as it is, is so sweet and playful it makes my teeth ache. I'm not saying, "Wouldn't it be awesome if we just, like, made all interactive media about relationships super fucked up?" Because good god, I do not want that.
But, I mean… Solas's romance is massively popular. Solas used and betrayed and then left you. It's not healthy. That's part of why it's interesting. When I confronted him in the Trespasser DLC, I kept thinking about how much I missed him. I was so desperate for him to just come back because I love you, you fucking ruinous elf, we can talk it out and Cole can make us hot cocoa and Iron Bull can cuddle all three of us! Idiot! And when he revealed his plan, which would almost certainly lead to widespread destruction and death… I still begged him to take me with him.
That was the story I wanted to see. It's not my favorite one, and it's certainly not what I personally would do in the Inquisitor's shoes. But I wanted to see that story, where a desperate Inquisitor throws everything away, damning everyone who's helped her just so she and her godlike lover can be together while the world burns. A hero who loses herself for love. It's kinda romantic, in a fucked up and awful way. More importantly, it's a complex, interesting story.
I want there to be more of those - stories about relationships that don't have nice bows on top to make them neat. Stories that indulge the toxic, unhealthy things we like but shouldn't, and let us explore it through fiction, with a glossy veneer of fantasy covering it. I don't want to be revictimized all over again, and I don't want these things to be touted as Actually Healthy And Fine, because that's messed up and not in a fun way! I want the freedom to write about these things without being afraid that people think I'm condoning them, or that I can't separate fantasy and reality, and I want to be able to do it without screaming "I'M A VICTIM, IT'S FINE" into a megaphone.
You know. Like Marie Antoinette said, "Let them eat dirt."