Tear Jerker / Ikemen Sengoku

• Every Dramatic route enters heartwrenching territory before the characters earn their happy ending (unmarked spoilers ahead!):
  • Nobunaga's has the very forces of time and space try to set the historical timeline back to its original version by having the wormhole determinedly chase them with the intent of sending the MC back to her time. Despite all their desperate efforts to outrun it, it catches up to them and Nobunaga realizes that if he keeps trying to hold on to her, she may very well die because of the temporal forces' second intent to kill him to undo his non-canonical survival. The final thing the MC sees before the wormhole sends her back is Nobunaga smiling at her with tears rolling down his cheeks — the first and only time he cries during his route — and saying that he's willing to die if it means that she'll live.
  • Masamune's is arguably the one with the least heartbreak, but still has the MC being sent back to her time against her will while she's desperately trying to save Masamune who's trapped underneath debris. Masamune's words to her just before they become separated, on how much he loves her and wants her to keep smiling and lead a happy life of her own even if they can't be together, manages to be both heartwarming and tearjerking at the same time.
  • Yukimura's has the MC learn that if she stays with him in the past, he will die protecting her. She decides that she needs to return to her time to prevent this from happening, but can't hold back her tears while lying to him that she doesn't love him enough to stay with him. Furthermore, she learns after she returns to her time that her return only caused him to live a little longer before he still died young with the implication that he became miserable and suicidally reckless in battle after the MC's departure, which means that her efforts to give him a better fate only ended up making things worse.
  • Ieyasu's has Ieyasu try to break the MC's heart to push her into returning to her time with Sasuke because he believes that she will die if she stays with him while they're fighting a losing battle with the enemies besieging them. The MC realizes what he's trying to do and tries to get him to change his mind, but he determinedly throws her out of their castle and shuts the door on her even as she's crying and begging with him to open up.
  • Hideyoshi's has Hideyoshi, who has served as a seemingly unshakeable protector and minder for the MC and the rest of the Oda forces so many times, fall into such a deep despair after he learns about Nobunaga's presumed death that his friends and the MC's efforts to try to talk him down from suicidally hunting down Nobunaga's killers on his own fall on deaf ears and we see just how truly broken he is underneath the surface and how he, in spite of having numerous people who love him for his kindness and support, still considers his own life to be worthless if he can't serve someone worthy because of the prejudice he suffered at a young age for being born of a low class. Furthermore, the MC is shown a Bad Future by the wormhole in which Hideyoshi abandons his ideals and alienates all his former friends after Nobunaga's death, becoming a wealthy and powerful but bitter and lonely shell of his former self who dies still believing his own life to have had no meaning — with the added Fridge Horror that this is very well what Hideyoshi could have become if the MC hadn't been there to save Nobunaga's life by complete accident/coincidence.
  • Shingen's has his main route already have the gut-punch reveal of him slowly dying from an incurable illness and not wanting the MC to become tied down to him and have her heart broken by his death as a result, but his Dramatic route twists the knife further by having the Hope Spot of him accepting the MC's proposal for them to take the gamble of traveling together to her time to get him treated by doctors be crushed by his former best friend Kennyo's betrayal that ensures the war will drag on too long for him to be able to catch the wormhole in time. His sad, resigned speech to the MC about how she should go back to her peaceful time and forget about him after he learns about this shows how he's come to treat his death as an inevitability after being ill for so long, and if it weren't for the MC's sheer determination to save him by any means possible, he would have simply given up on ever being saved. Not to mention how, after learning about Shingen's illness, every other route now has the Fridge Horror that Shingen almost certainly never gets cured and will die young in it.
  • Kenshin's main route is incredibly heartwrenching all by itself when it's revealed that he's never gotten over the tragic death of his first love Isehime who committed suicide after she and Kenshin were forced apart by his people who didn't approve of their relationship, and that he's so emotionally broken that constantly risking his life in battle is the only thing that makes him feel alive again. Even after he admits that he's fallen in love with the MC, it only makes him miserable because it causes him to have constant nightmares of her dying and brings out the paranoid, possessive side of him that never wants to let anyone else he loves die again even if it means taking away her freedom and happiness. And when the MC really does (almost) die just when it looks like he's made significant progress in overcoming his paranoia and possessiveness? Cue a Woobie, Destroyer of Worlds rampage that manages to be absolutely terrifying and absolutely heartbreaking at the same time.
• Individual scenes that qualify for this trope:
  • Kenshin's Breaking Speech to Kennyo in his Romantic route that manages to be both cruelly merciful and sadly understanding at the same time:
    Kennyo: Why? Why won't you kill me? Is the mad god showing compassion now?!
    Himezuru Ichimonji cut a clear line down Kennyo's monk cassock. Kennyo held the torn fabric together over his chest.
    Kenshin: That wasn't compassion. I did what you asked; I killed your heart.
    Kennyo: My heart? What is this? A lesson given by a child? My heart died long ago.
    Kenshin: Then why do you still cling to the cloth of your faith instead of donning armor? Why do you sheathe a blade in a prayer staff instead of using a real sword?
    Kennyo looked down at his ripped robes and his splintered staff, lips trembling.
    With cold eyes that saw through the lies, Kenshin looked down at him.
    Kenshin: You don't dress that way to remember the death of your brethren. You were scared to give up the noble path you'd walked so long. You fear the demons that men can become.
    Kennyo: Do you think...you understand me?
    Kenshin: I do. Because I was you up until very recently. Just hours ago, I would have killed you and decimated the Oda forces.
    Kenshin: You're not in my hands anymore. You'll be a guest in Azuchi's dungeons. There, you will spend every day looking down at your tattered cassock. I took the last thing you wanted to hold onto — that's my revenge on you.
    Kennyo's moan resembled a sob.