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▲* {{spoiler|Freckles. Freckles, Freckles, Freckles. Dear God. ''Freckles.''}} After that particular piece of nastiness, Ciel's grasps at redemption were pretty sad to see. "Would you like an orange, sir?"
* The whole end of the circus arc was this.
* In chapter 44, watching Maylene and Finnian's breakdown after it seems to seriously and completely dawn on them that {{spoiler|Sebastian is dead}} is utterly heartbreaking. {{spoiler|Luckily, Sebastian is not really dead.}}
* The final episode of anime season 2 which is either a [[Bittersweet Ending]] or an outright [[Downer Ending]].
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* Chapter 57. Elizabeth is about to be {{spoiler|seemingly killed by a horde of zombies.}} "I wanted you to think I was cute, up until the end..." Cut to absolutely heartbreaking shot of Ciel's face.
* Elizabeth's backstory in chapter 58. {{spoiler|At first, we see her as a genius at fencing}}, but Ciel doesn't know that and is happy to marry just plain sweet Elizabeth, and she promises to be a wife he can protect. Then when Ciel returns with Sebastian and she realizes she's now taller than him, she wishes to be a wife to protect him.
* The end of the second musical. Eric's willingness to do anything to save Alan in itself is pretty tear-inducing, but it gets even worse when {{spoiler|Eric ends up not only failing, but also being the one who kills his friend, shortly before he is killed by Sebastian.}}▼
* Chapter 61. When {{spoiler|Sebastian gets stabbed by the Undertaker; especially when Sebastian reaches out to grab Ciel's hand, but then gets a giant death scythe through his body. Cue the beginning of a dramatic flashback.}}
* In the anime, Ciel appears downright cruel at times, although in the manga, he is simply just icy and elitist. It's eventually revealed that he was a happy, loving, carefree child before his tenth birthday. Then his parents were murdered, the mansion set on fire, and he was kidnapped. He was locked in a cage with other children his age and eventually was to be a child sacrifice until he called upon a demon in his desperation to live.
* The scene in Chapter 41 where Ciel straddles Sebastian's supposedly dead body, buries his face in Sebastian's throat and insists his butler was never to leave his side.
** I know! {{spoiler|Seeing Ciel break down over Sebastian's body made me think "He really does have some kind of heart" because he's always been a jerk. Then we find out Sebastian dying was all and act by Ciel anyway, which totally crushed my hope.}}
== The Musicals ==
▲* The end of the second musical. Eric's willingness to do anything to save Alan in itself is pretty tear-inducing, but it gets even worse when {{spoiler|Eric ends up not only failing, but also being the one who kills his friend, shortly before he is killed by Sebastian.}}
* Go listen to Unmei from the musical. [http://www.youtube.com/watch?v=GkblrSfOCro I'll wait.]
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[[Category:Tear Jerker/Anime]]
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