Fire Emblem: Three Houses/Tear Jerker

General

• A lot of the students and faculty at Garreg Mach have had difficult lives, especially some of the nobles. Their supports really delve into these things, but some bits of their dialogue hint at it or outright discuss it, and it can be heartbreaking.
• Mercedes and Jeritza aka Emile aka the freaking Death Knight, full stop. They're half-siblings and they were closer than anything until Emile's father, Count Bartels, threw Mercedes and their mother out of the house. Emile had a terrible childhood that culminated in him snapping and murdering his father and all of House Bartels upon discovering the man planned to kidnap and force Mercedes to marry him for more Crest babies. He distances himself from his beloved older sister to protect her from his murderous other half, the Death Knight, but she won't hear of it. In Crimson Flower some of the sadness can be mitigated, as Jeritza is playable thanks to a free DLC upgrade; he can support with Mercedes, be rehabilitated, and come home to her and her mother. In other routes, though? He's a mandatory kill. It's especially painful in Azure Moon if you complete Mercedes and Caspar's paralogue: Jeritza dies leaning on his sister's lap (CG inclucded) as Mercedes weeps and apologizes for not being able to save him from this fate.
• Felix's backstory. He used to be a sweet kid until the Tragedy of Duscur, during which his beloved older brother Glenn was killed. Felix never properly deals with his grief, letting the tragedy turn him into a cynical asshole who HATES chivalry and knighthood with all his heart because they took his brother away from him. Yet even when he pretends to be a cynical lone wolf, it's clear he's still hurting and refuses to confide in anyone about his feelings, at least to a point where he can start to let himself heal.

Part One

• The students' reactions to their first in-game kills. Some are kinda nonchalant, others apologize to their victims, and some even have Heroic BSOD's.
• The third chapter doesn't waste any time with the angst, especially if you're playing the Blue Lions route. Ashe's beloved adoptive father Lonato leads a rebellion against the church as revenge for the execution of his heir and eldest son, Christophe; he drags the local villagers into it, and Ashe is beyond horrified even as he tries to talk Lonato down. He fails, Lonato must be killed, and poor Ashe does not get over it so quickly. Even when he manages to bounce back and smile again, he still sounds wistful whenever he talks about Lonato.
• Jeralt's death, dear fucking lord. He doesn't even get a Dying Moment of Awesome like other FE dads such as Elbert or Greil. He's killed by a cheap shot to the back while his killer smugly scolds him for "interfering in their brilliant plan." As he dies in Byleth's arms, it's the first time Byleth ever is able to shed tears, and Jeralt lampshades this by saying he's happy. You even hear poor Byleth's sobs as the rain falls and they cradle their father's dead body....
  • Worse is Leonie's reaction. She idolized Jeralt and was so happy to be reunited with him, and now he's gone. She actually breaks down in tears when the player talks to her during exploration mode in the next chapter.
• Sylvain's deals with his older brother and the Lance of Ruin. Miklan Gautier is a piece of garbage and Sylvain has no qualms about kicking his ass in battle and humiliating him...and then Miklan turns into a monster from trying to use the lance without a Crest. They're forced to put him down, and Sylvain hurts badly over it even if there was no love lost between the two.

Part Two

• Edelgard's death on the Verdant Wind and Silver Snow routes. After you defeat her, it switches to an animated cutscene in which she tearfully begs the Avatar to finish her, realizing that her grand plans and ambitions have caused nothing but pain and bloodshed. Her final words are about how she longed to walk beside them, and when the deed is done the Avatar is clearly heartbroken about it.
  • It's worse in Azure Moon. Not only is Edelgard the final boss, she's transformed into a Hegemon Husk by releasing the power of both her Crests, and it's clear it's not just for the sake of ultimate power. Depending on the player's recruitment and gameplay tactics, by now all of the Black Eagles are likely dead. Including Hubert, who will remain by her side no matter what and is expressly devoted to her on every playable route. Her actions reek of desperation more than anything. Worse? When defeated her, she reverts to her human self and Dimitri offers her his hand, attempting a truce. She promptly attacks him and he retaliates, killing her, and many players interpret this as a case of Suicide by Cop. The final nail in the coffin? Dimitri, once obsessed with ending her life, is crushed by this outcome.
• Rodrigue's death on the Azure Moon route. He takes a fatal blow to protect Dimitri, and tells him with his dying words to live for what he believes in.
  • Worse, when Dimitri begins to regain his sanity and apologize to the others, Felix is clearly hurt over his father's death despite constantly, loudly proclaiming his hatred for the man. The Ashen Wolves DLC expansion has Yuri mention he saw the two talking, though, so it's possible father and son were on their way to reconciliation...and then, this happens.
  • Even more, Rodrigue's killer is Fleche, a girl who was utterly and completely shattered by the death of her brother Randolph due to Dimitri's actions (yes, Byleth killed him technically speaking, but they did it because the still not back to himself Dimitri was planning to torture him to death), and is hell-bent on revenge. Dimitri was unwilling to fight her, as his actions were starting to sink in, and then Rodrigue took the hit and sacrificed himself; then Byleth mortally wounds her, and the poor girl dies begging for Randolph to save her. And even more so, it offers a HUGE contrast with her behavior in Crimson Flower when Randolph gets killed in action, where she's very hurt over it but manages to keep her sanity.
• If the player failed to complete "War for the Weak", Dedue is officially dead. Gilbert tries to encourage the others to move on and honor his sacrifice, but it's clear that this loss is what fully broke Dimitri over the time skip. When the player approaches Ashe, he sounds like he's going to cry as he talks about how much he misses Dedue.
  • Even if the player completed the paralogue, the game still treats Dedue like he died until he returns in chapter 16.
• Dedue's ending in Verdant Wind/Silver Snow. After Dimitri is killed offscreen (Verdant Wind) or disappears and is all but screamed that he was killed (Silver Snow) in the battle of Gronder, he offers his aid in taking down the Empire. If he survives the battle, he destroys Edelgard's dead body before leaving Fodlan, an empty look in his eyes. Dimitri was really all he had, the only person he felt he could trust with all his heart, and now that he's gone he clearly feels he has no purpose anymore.
• Learning from Annette that Gilbert was among the casualties of Gronder in Silver Snow. While he doesn't make any appearances in Verdant Wind either, he's said to survive and carry Dimitri's dead body back to Faerghus, so at least Annette has a chance to reconcile with him after the war ends. In Silver Snow, that chance is gone and Annette is absolutely heartbroken.
  • Even worse is that Gilbert pays Byleth and Seteth a visit at the Great Bridge after it's been captured, asking them to join forces with Dimitri, who's been alive and in hiding throughout the timeskip. Unfortunately, Seteth says the Knights of Seiros cannot afford to at the moment after taking heavy losses at the bridge, and Dimitri cannot afford to hold off his advance any longer. This is the last time you see Gilbert alive and worse, he knows he's likely to meet his end during the battle, plus Seteth understands it too and feels terrible about it.

Seteth: And may the goddess protect you as well.

She could not.

• Silver Snow in general. It ends with all three major powers wiped out; Edelgard dead, Dimitri either is dead or missing (but the first option is far more likely), and Claude is "missing in action." Considering the three house leaders are the first non-Jeralt people Byleth associates with and were the driving force of the game for the most part, a world where none of them are still around is heartbreaking. Furthermore, all three major territories of Fodlan dissolve as the Church of Seiros basically takes over the continent and Byleth basically protects the status quo, as no mention is made of a reform to the church's practices that caused such unrest in the first place.
• Talking to Felix after the Gronder Field battle in Verdant Wind and Silver Snow. He'll talk about how Dimitri had been his best friend since before they were born, and how only now does he realize how blind he'd been to Dimitri's anguish following the Tragedy of Duscur before wondering if, had he taken a less hateful approach, he could have stopped Dimitri and saved him from going down such a dark path. For all his criticisms and acidic jabs at Dimitri, he never stopped caring for him deep down and regrets his choices to distance himself and stay angry at him.
• Recruit Dorothea in Azure Moon or Verdant Wind. At the same time, do NOT recruit Ferdinand. Then, when it's time to fight the latter at the Great Bridge of Myrdinn, pit him against her. This will trigger a VERY emotional scene where she will tell him how disappointed she is in him, and then he tells her she wouldn't understand him and urges her to fight him... Even more, Byleth's next talk with Dorothea will add a line where she all but sobs "I had to fight Ferdie, Professor! And I had to kill him!"
• In Crimson Flower, you can kill Flayn in front of Seteth. If you do, Seteth's reaction is an agonised BigNo as he watches beloved daughter die right in front of him.

Paralogues

• "Retribution," Ferdinand and Lysithea's paralogue. The two go into Hrym territory to quell some bandits and save Duke Aegir...only to discover they already killed him. Ferdinand's reaction is heartbreaking, right down to a voiced, choked sob in his dialogue. Duke Aegir was a pretty terrible person and Ferdinand had issues with the way he did things, but unlike others who could never forgive their parents for their screw-ups, Ferdinand still had a great deal of respect for the man.

Supports

• Claude revealing his backstory to Marianne in their final support. He doesn't say the little boy in the story being bullied for his mixed heritage was him, but it's plainly obvious.
• Ignatz and Raphael's first two supports. Raphael just wants to be friends, and Ignatz has been pulling away from him because he blames himself for the accident that killed Raphael's parents.
• Catherine and Ashe's supports get to the root of what caused Christophe Gaspard's execution and Lonato's anger at the church, causing Ashe even more heartbreak and frustration. He resents Catherine for turning Christophe in and the church for letting this happen, even though he knows it was the Western Church pulling the strings all along. And he feels guilty about resenting Catherine!
  • It's hard for Catherine, too. Christophe was her close friend from their academy days, and the whole time she wanted to cry out in protest at his execution. But she stayed quiet out of her loyalty to Rhea, and still regrets it.
• Caspar mostly comes off as a typical shounen hero, but he has a massive guilt complex for his father Leopold's role in the subjugation of Dagda and Brigid, as shown in his supports with Shamir and Petra. He takes a long time to move past it, but not before putting his life in danger to help Shamir in their supports.
• Ashe and Dedue's final support has the former tearing up as they discuss their lost loved ones and how to keep their memories alive.
• Sylvain's final support with Mercedes is both this and a Heartwarming Moment. They discuss his issues with women and his Crest Angst, and Mercedes's on-the-nose observations are enough to bring Sylvain to tears. For all his bad behavior with women and overly carefree attitude, he's had a rough life. Even as he tries to move on and smile and focus on his studies, some of the emotional wounds run deep and it's going to take a while for them to heal.
• Felix's first support with Mercedes has her attempting to dote on him and saying he reminds her of her own little brother, to the point where Felix gets annoyed and tells her to go away. After she leaves, his face turns sorrowful and he murmurs about his own brother. Without ever even seeing Glenn in a flashback this says all we need to know about how close they were, and how upset poor Felix still is about his death.
  • Felix's A support with Dimitri has them discussing the deaths and slaughter that they've dealt with through the war, and Felix will be quite bitter about it. As they talk about the death of Glenn and Rodrigue's Heroic Sacrifice, he outright tells Dimitri that he still wonders every single day why is he alive whereas the others did not, and accepts that he will have to live with such thoughts without wallowing in them.
• In Lorenz and Lysithea's C support, Lorenz tells Lysithea they should become friends since he's looking out for the future of Fodlan and Lysithea is the heiress to the Ordelia family. Lysithea is standoffish towards Lorenz, and when he leaves, she mutters to herself that she doesn't have a future to look forward to.