Heartwarming: Legend of Heroes: Trails in the Sky

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. Doubles as a Tearjerker.
  • While it only compounds the tragedy of the ending, Joshua's Love Confession to Estelle is rather touching, even if he is abandoning her.
    Joshua: You had me from the first moment I met you. I've always loved you. Goodbye, Estelle.

Second Chapter

  • The reunion scene between Estelle and Joshua, regularly cited as one of the favorite scenes in the series in official polls.
  • During the end of Chapter 8: first, Alan Richard and Kanone Amalthea swoop in an awesome Big Damn Heroes moment, saving Grancel, the Queen and our protagonists, showing that they have become proud allies of good, then, after the danger is passed, you receive frightening news: the Erebonian army is marching towards Liberl, and they conveniently already have steam-powered tanks. Then, you find Olivier, of all people, leading them. Oh, and he's apparently an Imperial prince. He gives all the impression of having played you and your group for a fool all that time, betraying you at the worst possible moment... then, Estelle stands up to him and it's revealed to have all been a plot by Cassius and Olivier to delay the Imperial invasion. And not just that, but Olivier is actually planning to overthrow the Evil Chancellor of the Empire and goes on to deliver a heartwarming speech about how he wants the Empire to be a power for peace, remembered for its accomplishment, not for its violence. Goes to show that, deceptiveness aside, Olivier has always worked for the good of all, and always was a genuinely good person.
  • Axis Pillar has two of these. First, Estelle giving Renne a Cooldown Hug. Which works. Second, Joshua and Loewe's reunion after the former persuades the latter to leave Ouroboros.
  • Seeing the other members of Ouroboros mourn Loewe in their own ways in Loewe Monogatari is pretty heartwarming

The 3rd

  • The entire premiese of Moon Door 5, where the orphans at Mercia look for a birthday present for Theresa.
  • Estelle's indefeatably enthusiastic attempts to cheer Joshua up shortly after he arrived at the Bright household, primarily by trying to collect as many interesting insects as she could find until she got one that could catch his attention. She never found the right bug but wound up catching his attention anyways when she caught a swarm of bees by accident.