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* John's death.

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* John's death. He's been poisoned by Lord English's fang, and despite claiming that everything's going to be fine, [[SecretlyDying it's implied he knew all along that nothing could save him]].
** His DyingConfessionOfLove is also incredibly painful - he doesn't even manage to spit it out before he drops dead, with no hope of a resurrection.
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* Jake's status as a HenpeckedHusband throughout the story is incredibly depressing as well. Jake's horrible situation isn't played for comedy in the slightest, and while he's OutOfFocus for much of the story, the narrative goes to great lengths to show just how miserable he is whenever he shows up. Jane uses copious amounts of alchohol and the lollipop juju to rape him, which she gets pregnant from. Jake then feels forced to father the resulting ChildByRape, all the while not really knowing how to feel about the situation. As time goes on, Jane's mental state continues degrading as she slowly becomes ANaziByAnyOtherName. Near the end of their relationship, Jake is terrified to even talk to Jane, walking on eggshells around his mentally-unstable wife, presumably because he's afraid that she might kill him or their son if he dares speak against her.
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* Dirk using his control of the narrative to break Rose and Kanaya up by making Kanaya assume that since Rose has spent so long at Dirk's the two of them are in a relationship now.
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I thought he was a human child?


* Tavros Crocker's entire situation is just one big showcase of things that [[HarmfulToMinors absolutely should not happen to a child]]. He's been forced to live in an unhealthy household with [[ANaziByAnyOtherName Jane]], [[DarkMessiah Gamzee]], and [[HenpeckedHusband Jake]]. Even as a small grub his parents argue and have kismesis relations in front of him. Later, he proves to be way more knowledgeable about his mother's eugenic political beliefs [[TroublingUnchildlikeBehaviour than any child should]]. John has reason to suspect that Gamzee is grooming him both in the sense of raising him to be a successor and... [[PedoHunt something else]]. The poor kid just seems so miserable, and it's clear he's getting his childhood taken away from him. No wonder John alienates everyone by trying to take Tavros away to live with him.

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* Tavros Crocker's entire situation is just one big showcase of things that [[HarmfulToMinors absolutely should not happen to a child]]. He's been forced to live in an unhealthy household with [[ANaziByAnyOtherName Jane]], [[DarkMessiah Gamzee]], and [[HenpeckedHusband Jake]]. Even as a small grub baby his parents argue and have kismesis relations in front of him. Later, he proves to be way more knowledgeable about his mother's eugenic political beliefs [[TroublingUnchildlikeBehaviour than any child should]]. John has reason to suspect that Gamzee is grooming him both in the sense of raising him to be a successor and... [[PedoHunt something else]]. The poor kid just seems so miserable, and it's clear he's getting his childhood taken away from him. No wonder John alienates everyone by trying to take Tavros away to live with him.
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* Tavros Crocker's entire situation is just one big showcase of things that [[HarmfulToMinors absolutely should not happen to a child]]. He's been forced to live in an unhealthy household with [[ANaziByAnyOtherName Jane]], [[DarkMessiah Gamzee]], and [[HenpeckedHusband Jake]]. Even as a small grub his parents argue and have kismesis relations in front of him. Later, he proves to be way more knowledgeable about his mother's eugenic political beliefs [[TroublingUnchildlikeBehaviour than any child should]]. John has reason to suspect that Gamzee is grooming him both in the sense of raising him to be a successor and... [[PedoHunt something else]]. The poor kid just seems so miserable, and it's clear he's getting his childhood taken away from him. No wonder John alienates everyone by trying to take Tavros away to live with him.
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** This doubles as NightmareFuel when considering his actions during the Meat timeline.


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[[folder:Meat]]
* John's admission of depression after being trapped in the house juju is heartbreaking.
* John's death.
[[/folder]]
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[[folder:Candy]]
* Dirk's suicide, especially since it serves as a MoodWhiplash for the story. His reasoning for doing so also qualifies: he felt as though he had no place in the Candy timeline.
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For examples from the [[Webcomic/{{Homestuck}} main series]], go [[TearJerker/{{Homestuck}} here]].

'''Unmarked spoilers ahead!'''
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[[folder:Prologue]]
* Picking up seven years after Act 7, we see that John's become increasingly isolated. He barely talks to his friends anymore, lives alone mourning his dad, and [[AloneAmongTheCouples had to watch all his friends pair off]] and live HappilyEverAfter without him... including Roxy, for whom he clearly still has [[UnresolvedSexualTension unresolved feelings for]]. He regrets wasting his later teenage years and can't stop thinking about what might have been.
* Rose pops a lot of pills during her talk with John. She claims she's doing it in a manner prescribed by her doctor, but despite her reassurances to John, it's possible she's relapsed into substance abuse.
[[/folder]]
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