I am an absolute masochist when it comes to reading.
To me, bittersweet is the best kind of story. You feel with the characters, for the characters, you’re experiencing the pain and sadness along the path and it registers somewhere. It means you’re invested, that you care for them. It highlights the good times, showcases the struggles, and makes something poignant of their journey.
Moments that stick with me aren’t the traditional ‘and they all lived happily ever afters.’ They’re the Titanics, The Notebooks, the Green Miles. They’re the scenes with uncle Iroh singing to his son, the moments when Travis faces Old Yeller. They don’t have to be downright bleak and despair, or the ending; they can be just as happy as they are sad, or offer the glimmer of something more (a la Gone with the Wind), and be landmarks along the way instead of the final destination. It doesn’t have to be death, either. It can be loss, it can be moving on, it can be a breakup, or settling for something. But overall, they’re amazing when you accept it, you appreciate it because it’s so good, but all the while feeling like your heart is breaking into a million pieces and you have the urge to throw your book/phone simultaneously.
Now, this doesn’t mean that elements of tragedy make something good. (Similarly, happy endings also don’t mean it either.) They can be implemented terribly just like any other story elements. It has to fit, it has to serve a purpose, and it can’t be there just to be there.
On that note, I find including these types of scenes/endings into choice games very interesting. If you have ‘good’ endings where everything is happy and awesome in the end, but in some endings someone died or so and so was lost, it implies that one is better than the other. It means there’s a right and a wrong way to do something, and right and wrong endings. Some might require more strategy, might be harder to achieve, but in the end I consider this a mechanical feature (you didn’t pass x stat, or you chose the wrong options here, etc.) rather than a narrative one. I think good tragic or bittersweet moments have to be narrative and require planning + the right genre/type of story, and these can fit into all the different paths by being different things.
And going with tricky, it’s also very difficult making it so the player doesn’t feel punished. There should be something that comes out of these moments, too, and something that still feels satisfyingly good even if it’s still heartbreaking in other ways.
But now I am going off on some weird tangent. In conclusion, yessss! I love heart wrenching things and haven’t really seen them incorporated here other than in mechanical options so far. I’d love to see more.