* The whole premise, really; Italy going back in time, over and over, to try and save friends that just keep dying and leaving him all alone again. Rinse and repeat.
* Also regarding Italy, his dialogue when they're in the basement and he realizes that someone has forgotten to lock the door behind him. He stands with his back to it and tells everyone else to run and not look back ...
** "Please... Please, if you get out, just keep running. No matter what, don't look back, don't forget about me, don't blame me, don't cry, and timeó" ... Telling people not to cry was clearly a futile action, Italy.
* Try to watch one of its various [=MADs=] without breaking down and crying. I dare you.
** [[http://www.youtube.com/watch?v=7A625KwZdrs Just to put an example.]]
* The music from the game can be pretty sad too. Particularly, [[http://www.youtube.com/watch?v=7qSqL7EYnxI&feature=related this song.]]
* Most, if not all, of the characters' various last words are absolutely heartbreaking:
**
--->'''America:''' I want to stay with them (Canada and England). Till my last moment. Because they're both very important to me.
--->'''Italy:''' And because you're going to... protect meó
--->'''America:''' Haha! Yeah. Even though I can't even move any more. But I'm not making a mistake. And I regret nothing. [...] Go for it. I wish you luck.
**
--->'''Germany:''' Anyone who... disobeys... will run... ten laps...
--->'''Prussia:''' ... Look... if you don't... hurry up... he'll keep adding even more.
--->'''Italy:''' Fine! I'll run!! I'll run ten laps! I'll run as many laps as you want! But I'll run away! And then Germany... will have to run... to catch me...
**
--->'''America:''' England
--->I was a hero, wasn't I? I protected you, didn't I?
--->I could be a hero... couldn't I?
** Russia being the last one to die out of China and France.
---> "Even in this place ... I'm all alone again."
** [[spoiler: Italy's death and Germany's reaction to it during the second time loop.]]
-->[[spoiler:'''Italy:''' I...did it... I... saved... everyone! I made no mistakes...!]]
-->[[spoiler:'''Japan:''' Italy!]]
-->[[spoiler:'''Italy:''' Hehe... Your injury looks serious... but you're alive, so you'll heal. Thank God... thank God I became Ryuuzu...]]
-->[[spoiler:'''Present!America:'''(...? Ryuuzu?)]]
-->[[spoiler:'''Italy:''' Guys, you may not know this, but... this is actually the second time we came here... The first time, I wasn't useful... at all... I could finally get you back... Thank God... But I'm sorry... now it's my turn to fall...]]
-->[[spoiler:'''Germany:''' You've got to be kidding-- The second time?! That makes no sense!]]
-->[[spoiler:'''Italy:''' I went back in time, you see... I managed to get out of here. But I was the only one... who got out... I didn't want that. I had to get you all out...]]
-->[[spoiler:'''France:''' You-- you idiot! You didn't have to get us out! You had to get out ''with'' us!]]
-->[[spoiler:'''Germany:''' I-Italy...]]
-->[[spoiler:'''America:''' Q-Quickly, let's carry Italy... Anyone?! Isn't there anyone who can move?! What about China and the others? Aren't they back yet?!]]
-->[[spoiler:'''Prussia:''' Make...make a place where we can rest! It can be anywhere! I'll look after him! A really safe place! Someone!!]]
-->[[spoiler:'''Italy''' (I can hear their voices... I was all alone back then, but now they're alive. I'm so happy... I'm so happy, but...) Hey, Germany...]]
-->[[spoiler:'''Germany:''' H-Hold on... Italy... Oh, I know! I will make a place for you. The best place for you to rest at ease...]]
-->[[spoiler:'''Italy:''' Really? Heheheh. Then, will you make lots of beds... where everyone can rest? And then I'll peacefully rest... between you and... Japan...]]
-->[[spoiler:'''Germany:''' Yes...]]
-->[[spoiler:'''Italy:''' And a biig table, too. I also want a place... where we can all cook...]]
-->[[spoiler:'''Germany:''' Yes. Definitely...]]
-->[[spoiler:'''Italy:''' ..........Ger...many...]]
-->[[spoiler:'''Germany:''' Yes, Italy?]]
-->[[spoiler:'''Italy:''' I... I don't... want to die here... I wanted to escape with all of you.....]]
-->[[spoiler:'''Germany:''' Italy? Italy? Italy.......Italy! ITALY!!]]
-->[[spoiler:'''England:''' No...]]
-->[[spoiler:'''Prussia:''' Crap... Japan, take the others outside, West is out of control!]]
-->[[spoiler:'''Germany:''' Italy!! Italy!! Stop screwing around! Your eyes are open! Italy!! Italy!!]]
-->[[spoiler:'''America:''' Germany is--]]
-->[[spoiler:'''Prussia:''' West! Calm down! France! Please, Gimme a hand here!]]
-->[[spoiler:'''France:''' Italy is...No... It's impossible... Wait... Why...]]
[[spoiler: And then the rest of that scene is everyone reacting to it, making the Tearjerker even worse.]]
** It was so sad that even Japan, yes [[TheStoic Japan]] started to cry.
* Second time loop!Germany's conversation with present Italy.
* America's "How many fingers I'm holding up?" to a [[spoiler:blind]] England.
* There's a video on Website/YouTube that has ''Disney/{{Tangled}}'''s Healing Incantation makes it very tearjerking as it's about North Italy wanting to make things right, but goes FromBadToWorse
** There's a [[http://www.youtube.com/watch?v=65NvOnYyfcw slideshow]] and [[http://www.youtube.com/watch?v=x60-3J8P7hk animated]] version.
*** There's even a [[http://www.youtube.com/watch?v=2zul7g1hcN4 male version in Italian]] the other lyrics are heartwrenching but when the lyrics of this version are put in the context of Hetaoni and you imagine Italy clutching the notebook to his chest and singing them... They become ''heartbreaking''.
* The first line of [[spoiler: past]] Italy's letter.
---> '''Italy:''' To the me who lives at some point in time... and isn't alone-.
* Just watch this, and try not to cry http://www.youtube.com/watch?v=7h-V88Z_bis her are some of the lyrics: How much longer will I have to cry? When can I join my friends? Is this my turn to die?... *sniff*
* The scene with Russia and [[spoiler:Belarus]] can be either this or a CrowningMomentOfHeartwarming depending on what you think but [[http://www.youtube.com/watch?v=HDM_G3L0VhM&list=PLE9A9ECBBD067E83F&index=15&feature=plpp_video the music in that scene]] definitely counts as this.
* Perhaps in more of a FridgeHorror kind of way, but second-time-loop!England's conversation with current-time-loop!Spain may count as this; when Spain tells him about the situation and asks him to send his magic to current!England, the past England explodes and says that, even if he is just a false and meaningless past to Spain, this world is everything to him, and he can't simply give it up for the sake of some alternate reality he, and the loved ones he knows, will never see. Even worse when you realize that, as a result of this conversation, this England now knows his world is doomed; and on top of that, this is the same England that will wind up doing the HeroicSacrifice to save current!America, Italy, and Germany, which was a massive tearjerker itself.
** This England is the source of another massive tearjerker later, when his HeroicSacrifice spell barely manages to save current!America; he explains to America that, though America may be a hero, England is a gentleman, and will always go first into the fray... and sends America back to the future, presumably only to be joined by his timeline's America, who insists on being the hero and staying with this England while the room explodes around them. So he ''does'' wind up giving up his world for theirs; and, in the process, has to see the very person he intended to protect die anyway, albeit in a different form.