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• 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 time—" ... 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.
  • Just to put an example.
• The music from the game can be pretty sad too. Particularly, 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 me—
    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."
  • Italy's death and Germany's reaction to it during the second time loop.
  Italy: I...did it... I... saved... everyone! I made no mistakes...!
  Japan: Italy!
  Italy: Hehe... Your injury looks serious... but you're alive, so you'll heal. Thank God... thank God I became Ryuuzu...
  Present!America:(...? Ryuuzu?)
  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...
  Germany: You've got to be kidding— The second time?! That makes no sense!
  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...
  France: You— you idiot! You didn't have to get us out! You had to get out with us!
  Germany: I-Italy...
  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?!
  Prussia: Make...make a place where we can rest! It can be anywhere! I'll look after him! A really safe place! Someone!!
  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...
  Germany: H-Hold on... Italy... Oh, I know! I will make a place for you. The best place for you to rest at ease...
  Italy: Really? Heheheh. Then, will you make lots of beds... where everyone can rest? And then I'll peacefully rest... between you and... Japan...
  Germany: Yes...
  Italy: And a biig table, too. I also want a place... where we can all cook...
  Germany: Yes. Definitely...
  Italy: ..........Ger...many...
  Germany: Yes, Italy?
  Italy: I... I don't... want to die here... I wanted to escape with all of you.....
  Germany: Italy? Italy? Italy.......Italy! ITALY!!
  England: No...
  Prussia: Crap... Japan, take the others outside, West is out of control!
  Germany: Italy!! Italy!! Stop screwing around! Your eyes are open! Italy!! Italy!!
  America: Germany is—
  Prussia: West! Calm down! France! Please, Gimme a hand here!
  France: Italy is...No... It's impossible... Wait... Why...

• It was so sad that even Japan, yes Japan started to cry.

• Second time loop!Germany's conversation with present Italy.
• America's "How many fingers I'm holding up?" to a blind England.
• There's a video on Youtube that has Tangled's Healing Incantation makes it very tearjerking as it's about North Italy wanting to make things right, but It got worse
  • There's a slideshow and animated version.
• The first line of 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*