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Tear Jerker / The Legend of Heroes: Trails in the Sky

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First Chapter

  • The immediate aftermath of the school play in FC, where Jill reveals that the school has been running a donation campaign so Theresa can rebuild the orphanage that means so much to her. And then she's immediately mugged and all the money is stolen. Thankfully things get better, but it's still a huge blow.
  • The ending of FC is absolutely heartrending, as Joshua reveals his past to Estelle about his involvement with Ouroboros, which ends with him sedating Estelle, and promising to leave her alone from now on. Estelle's reaction throughout is what amps up the Tear Jerker quotient so high, as seeing someone as Bright and cheery as Estelle completely break down is horrible, to say the least.
    Estelle: STOP IT. Stop talking about it like it's a dream...! You make it sound like nothing that's happened was even real to you!
    • Just as bad, if not even worse in some regards, is Joshua's breakdown beforehand, upon having his memories restored and being told he was unwittingly feeding Ouroboros intel on Cassius ever since his adoption. FC didn't have much variance in dialogue portraits before this, mostly just a few tweaks to facial expressions... and you're suddenly hit with a portrait of Joshua keeling over, with Dull Eyes of Unhappiness. The music, which eventually segues into a slow, sad version of Silver Will, doesn't help matters either. And from Joshua's perspective, even after he regained his memories, he still at least felt the time he spent with Estelle and Cassius was genuine... only to be told this was also all part of Ouroboros' plan. The one ray of light in his life was also a lie.
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Second Chapter

  • The end of Chapter 3, where you find out that the Cheerful Child you've spent the whole chapter taking care of was Evil All Along and playing you the entire time. The music (which is the same as in the Tear Jerker moment from the first game's ending mentioned above) and writing does a great job of making the player feel just as betrayed as Estelle.
  • Loewe's death scene, as he finally realizes why Karin was able to smile when facing her own death, followed by Joshua breaking down after Loewe passes away.
  • The orchards in Ravennue Village being burned down by Ragnard. Not only is every single NPC utterly devastated by seeing their hard work being reduced to ashes in an instant, the village's economy, as one NPC makes clear, is utterly dependent on the trees. Which is to say, its quite unlikely it's going to survive that.
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  • Agate's past deserves a mention as well. His sister died in the Hundred Day War, which he blames himself for, and he even admits that as long as he puts all of his anger directed at himself into his sword it appears he's keeping it together.
  • Estelle and Joshua's reunion. Joshua tries to push her away again, and Estelle shuts him down by pointing out how he's lying about his reasons for leaving and that he's actually scared of losing her like he lost Karin. She reassures him that just as he protected her in the first game, she's ready to protect him too. She finishes her declaration by hugging him from behind, which causes Joshua to cry for the first time in 11 years.
  • The Hamel tragedy and the effect it's had on the survivors, including Joshua and Loewe. Doubles as Nightmare Fuel as well.
  • Possibly the most unexpected one comes from a minor character. In the city of Bose, you are introduced to Mayor Maybelle and her maid Lila. Throughout FC, their interactions are mostly comedic, with Lila playing the Straight Woman to the overworking Maybelle. Then in SC, one of the Bracer side missions involves finding a woman's lost niece who had been missing for 10 years. Given how other missions turned out, you'd expect a silly scene followed by a happy reunion, right? When you show the picture of the girl to Lila, it suddenly sets off her Trauma Button, and it's revealed she was an orphaned girl named Raini who lost her parents in the Hundred Years War, When she was taken in by Maybelle, she was so shocked that she forgot how to speak for a while, and so Maybelle's father gave her the name Lila so that she had a name. When confronted, Lila insists that Raini is long dead, but she was lying to avoid facing the painful truth. Fortunately, it ends with her aunt being understanding and with a promise they'll meet again in her birthplace someday. The whole scene really goes to show how many victims the war left in its wake that even NPC's have lasting trauma from it.
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The 3rd

  • The initial rift that exist between Kevin and Ries, which really comes to a point during chapter 4. Ries, who felt lonely and left out because she's the only new face in Phantasma and sees everyone else being close, was happy that Kevin seems to be making friends, even if she's hurt that he did so while avoiding her for 5 years; only to notice that that's not really the case, with Kevin basically putting an act with the others. Rather than admitting it, Kevin denies it, says that Ries is just being tired, and basically just doubles down on the act. You can just see how heartbroken Ries is, culminating in an Armor-Piercing Slap and her leaving the party for the whole chapter.
  • The conclusion to Chapter 6 as several characters are finally able to say goodbye to Loewe.
  • Chapter 7 is one long tear-jerker with a couple moments of heartwarming thrown in. The fact that this is the chapter where the game stops hinting at Kevin's past and has him tell the party what happened has a lot to do with this.
    • You can tell how bleak this part of the game is from the fact that, for the first time in the whole trilogy, there are no joke chest messages. Examining any open chest just results in "the chest is empty".
    • As part of Chapter 7, Kevin must face all of the sinners he has killed, and the game picks some choice ones. The first is Owen, a corrupt priest from the Church who hired the Jaegers to attack Aster House and who begins his rant by raging at Kevin before descending into a Madness Mantra about how agonizing his continued existence is. The second - and arguably most heartbreaking - is a young boy named Elmer who was turned into a flesh-eating monster by a devil-worshipping cult and who, despite Kevin attempting every form of Thaumaturgy he knew, could not be saved. Upon seeing Kevin and Riese in Gehenna, he begs them to allow him to eat them and sate his hunger; when Kevin states that the least he can do is kill him quickly, Elmer reacts with terror, claiming he doesn't want to die, he just wants to not be hungry anymore. The final miniboss faced is Kevin's mother, now a spectral ghost. The game does an excellent job of showing just how taxing these encounters are on Kevin, seeming to push him to the very brink of completely breaking down without actually cracking his facade.
    • It's heartbreaking that after every encounter Kevin will talk and elaborate on what happened or just to further deride himself on what he had become. Even after he killed his mother's ghost Kevin doesn't cry and keeps on talking, until Ries hugs him from behind and said that he doesn't have to force himself to talk with tears in her eyes.
  • Kevin and Ries' farewell with Rufina. The fact that she has to be killed once again in order to prevent another Phantasma from happening is heartbreaking enough, but then Ries decides to do it together with Kevin so they'd bear the sin together. Kevin tearing up as they did the deed, and then Ries just wailing in grief afterwards as Kevin held her close is such a fitting, sad and heartfelt end to their character arcs.
  • Star Door 15, the one that reveals Renne's past.
    • Joshua leaving on a mission and not coming back is this to poor Renne, especially because it's basically a repeat of what happened to her imaginary friends, leaving for work and then never returning. The fact that she's trying to convince herself that Joshua will come back only makes it more painful.
    • Renne finding her parents and calling them her real parents at first, even wanting to introduce Joshua to them. And then she saw their baby, overheard their conversation, and realized that from the day she was born she had never been wanted. It's very, very heartbreaking, especially when her parents are trying to forget about her and said that's probably what she'd have wanted, when in fact that couldn't be further from the truth.
    • Renne waking up from her dream sleeping on the ground in the wilderness somewhere, alone, as it's raining. Her portrait makes it clear that she was crying in her sleep, and she mutters that it's cold. Pater Mater then releases hot air to warm her up. it's a small act, but after everything we've seen of her past, it's really no wonder that Renne sees Pater Mater as her real parents when the archaism is practically her only constant companion who cares for her, because Joshua and Loewe are now gone from her life.
      • Making this more heartbreaking is that if one is playing with the EVO voice patch, then Renne thanked Pater Mater not by its name, but by calling it "Papa and Mama."
    • It's also clear after seeing this door why Renne became so angry at Estelle in SC when she said she shouldn't have joined Ouroboros or that she isn't happy. From her perspective, Ouroboros saved her and gave her a much better life, not to mention she could've seen it as Estelle insulting Loewe too.
  • The game's ending has shades of this. With Phantasmagoria starting to come apart, the characters bid their farewells to one another and, in ones and twos, start heading back through the doorway to the real world. One of the last to leave is Renne, who watches everyone else leave in silence. When Joshua and Estelle ask her about it, she explains that she can't understand why everyone would want to leave instead of just staying in the Hermit's garden and why they're all smiling as they go, even though everyone is sad. As the two of them try to comfort her, she breaks down in tears. Eventually, they explain that they've been looking for her in the real world to make her a part of their family; Renne, taken aback, promises to run away so far that she will never be caught. She dashes through the portal after screaming at them that she hates them... and that she loves them too.
  • A meta example: the chests in the final dungeon are filled with messages of encouragement from the translators and heartfelt thank-yous to the English-speaking fans for supporting the series in the west. Sadly, this game would wind up being the last of the Kiseki games that XSEED Games would translate, as NIS America took over the license starting with Trails of Cold Steel III.

Other

  • The first chapter of Loewe Monogatari with Loewe, Karin and Joshua living happily together. The Tearjerker aspect comes from knowing exactly what's going to happen in the near future.
  • The ending of the manga also manages to be this in spades. Seeing Loewe die again has just as much of an emotional punch as it did in the game, though it also has a heartwarming moment as Loewe and Karin's spirits watch over Estelle and Joshua.
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