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Tear Jerker: Hakuōki
The entirety of the game's "Normal Route" is one long tear-jerker. Chizuru, separated from the Shinsengumi during the battle of Toba-Fushimi, follows their progress across the country trying to catch up with them, and arrives at each location only to learn that the Shinsengumi have already withdrawn from the area and that another of the men she cared about and admired is now dead. She clings to hope up until she reaches Ezo and hears of Hijikata's death, at which point, finding a discarded Shinsengumi banner at the side of the road, she breaks down weeping.
Oh my God. My breath catches in my throat, and I feel a rush of blood through my body, warmth starting in the pit of my stomach and spreading through my chest and up to my face. Itís the kind of adrenaline you get in a moment of shock, where the body floods the system to be ready for anything, fight or flight. I am stunned. There are no words for this — I never expected this to happen. I never thought something like this would happen. Not to Kondou, not to anyone I knew. Even when everything was at its worst, even when we were under fire from artillery shells as we desperately attempted to evacuate Kyoto, I never thought Kondou or anyone else would die. ... All that up there? All those feelings, those physical reactions, that adrenaline? That was me in real life. Oh my God. THIS GAME.
The anime isn't much better. Episode 18 starts badly with a flashback of Kondou being executed, follows with Harada's implied death from a wound he sustained in a battle against Koudou and tops it off with Okita's Heroic Sacrifice as he uses up his life force to defend Hijikata from an assassin squad... Hijikata gets wind of what he's doing and, still badly injured, limps painfully out of town towards the spot, but by the time he gets there the only thing left is a bunch of dead bodies and Okita's sword.
Yamazaki shielding Hijikata from Kazama's sword with his own body, and his urgent speech to Hijikata while grievously wounded: "What are you doing, Vice-Commander? You're the leader and we're your subordinates. You can always replace your subordinates... But if we lose our leader, it's all over..."
Some of the bad endings go the extra mile to twist the knife:
The first possible bad ending of Hijikata's route has Kazama threatening to hurt Chizuru in order to get at Hijikata, which prompts Hijikata to lay down his sword over Chizuru's desperate protestations, saying that being a leader of the Shinsengumi means he's prepared to die for anyone under his command, including her. Kazama proceeds to torture Hijikata to death in front of Chizuru in order to teach her not to defy him.
In the final bad ending in Okita's route of the game he takes a mortal blow protecting Chizuru from Kaoru, and dies in her arms, regretfully lamenting that he's leaving her alone and asking her to tell him again that she loves him. To make matters even worse, this one has its own unique gallery image.
His last bad ending having its unique CG means that, if you want to get that trophy for getting all of Souji's C Gsyou have to get his bad end in a route that has enough pain and tears when you're taking the right choices.
Okita's route in the prequel is this as it gives a brief glimpse into his childhood and justifies his strained relationship with Hijikata. All Okita wants is to be useful to Kondou. Kondou (and especially Hijikata) would rather he go back to the safety of Edo and not stain his hands with the Roshigumi. All of Okita's efforts to be accepted basically boil down to one decision: does he want to stay Kondou's kid brother and keep him happy or does he want to become the Shinsengumi's sword which would help achieve Kondou's goals but hurt Kondou's image of him. He chooses the latter.
For that matter, anytime Kondou praises Hijikata in front of Souji.