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5[[quoteright:350:https://static.tvtropes.org/pmwiki/pub/images/r_3_7.png]]
6[[caption-width-right:350:"Why do I keep losing people? I came to the Digital World to get away from those feelings, but I just can't escape."]]
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12* Gomamon's torture from the episode "Old Reliable", and his weakened state afterwards is enough to bring any Gomamon fan to tears.
13** The fact that had Yolei not dropped her hand warmer, they may not have even ''found'' Gomamon, who was unconscious from his injuries and buried in the snow. It's just lucky he's implied, by his later stages, to be an arctic-aquatic Digimon, meaning he could survive being buried under frozen water.
14* Just how ''broken'' Cody sounds when the employee he's asking about Joe tells him that Joe can only leave his exam if someone's in danger of dying and he says, "But someone might be..." (paraphrased) while imagining the state his teammates must be. And even though he saved everyone, he ''still'' can't believe he deserves Reliability because he told a lie.
15* Poor little Agumon being placed under the Digimon Emperor's control not once, but ''twice''. The second time is an especially big punch to the gut to Taichi who had just got his best friend back, only for him to be taken away again moments later.
16--> '''Tai''': I let Agumon down just when he needed me the most.
17* Ken's backstory. Considering the absolute ''bastard'' he was as the Emperor, it's amazing that most of the things [[TheWoobie Ken Ichijoji]] does afterwards can bring a tear to a viewer's eyes to the point it can be hard watching earlier episodes before his HeelFaceTurn. From his first not recognizing his own mother after coming out of a [[HeroicBSOD not-at-all-Heroic-BSOD]], to seeing his dead brother in an [[LotusEaterMachine illusion]] caused by his own desire to see himself punished for his misdeeds, to Davis yelling that [[YouAreNotAlone he's not alone anymore]] while he's struggling with the serious mental and physical pain of trying to close a Gateway to the Dark Ocean that's haunted him since he was seven... This guy really had to [[EarnYourHappyEnding earn his happy ending]].
18** Wormmon's death. It's just downright heartbreaking; even Davis' group look they're about cry as well.
19--->'''Ken''': ''(scoops up the dying Wormmon in his arms)'' Wormmon, I'm sorry. Don't go. You're my best friend.\
20'''Wormmon''': You're my best friend, too. Goodbye, Ken. ''(disappears into digital code, and fades away)''\
21'''Ken''': Wormmon, no!
22** It's just as heartbreaking in the original Japanese;
23--->'''Ken''': Wormmon.. Were you.. Always this light?
24---> '''Wormmon''': Goodbye... Ken.. chan.. (disappears)
25---> '''Ken''': Wormmon?
26---> '''Takeru''': He's dead...
27** This is just after Ken having a ''heartbreaking'' breakdown as he realizes that the Digital World isn't a game and all the Digimon he'd been terrorizing, and enslaving were ''real living creatures with emotions'' instead of game constructs. His HeelRealization coupled with the revelation that because of him Wormmon, who he now knows was a living thinking creature, and did nothing but love him unconditionally, is now ''dying'' causes him to bawl in sorrow as he staggers around and tears his Digimon Emperor outfit apart piece by piece until it dissolves completely and he's just Ken again. What's worse, he starts flashing back to his older brother's death in a car accident as he realizes that [[HistoryRepeats he's just made the same mistake]] ''again'' of not knowing what he has until he's lost it. And to really rub salt in his wound it's at that point that his [=DigiDestined=] Crest comes to him now that he's regained his greatest trait. The Crest in particular? The Crest of ''Kindness.''
28** The scene where Ken goes into the Digital Nursery and all the Digimon start whining whenever he comes near them, and he finds Wormmon's baby form and holds it in his arms and starts bawling his eyes out.
29** The scene depicting Ken's relationship to his older brother. He both [[TheResenter resented]] and [[BigBrotherWorship admired]] Sam, an already hard position for a kid. And then, after the boys have a heated argument over the Digivice that came out of Sam's computer, Ken's finally pushed over the edge and in the heat of the moment, spitefully [[IWishedYouWereDead wishes his brother]] would just "[[NeverSayDie disappear]]". [[BeCarefulWhatYouWishFor And then tragedy strikes]].
30** Props to the dub for not sugarcoating Ken's backstory and giving it the acting it deserved. Despite NeverSayDie being in effect, it's painfully clear what happened to Sam, and it is heartbreaking to listen to this story unfold.
31** The worst part? ''[[BigBrotherInstinct Sam was just being a worried sibling]]''. While Sam slapping and yelling at Ken for using the Digivice was a bit rough for him, from a sibling's perspective, he could have lost Ken or worse, being that he was the oldest and has to look out for him, who knows what could happen as a result. Ken, meanwhile didn't understand due to being young (and having some resentment/worship of Sam) and just thought his big brother was being mean.
32** While Osamu had the more selfish motive of being jealous that Ken could use the Digivice and go on into another world and none of the noble intentions or dialogue that Sam had his position is ''really'' sad and understandable. The fact that his brother was the chosen one and the one who could go on adventures with his Digivice is a really hard fact to accept.
33** Also, his poor parents, who've already lost one son, reaction after he abandons reality for the Digital World near the end of the Digimon Emperor arc is sad to see due to his note announcing his permanent departure ''coming off as a suicide note.''
34** The cherry on top? It's very subtly implied that Sam died [[BigBrotherInstinct pushing Ken out of the way of the car]].
35** When the Chosen Children are trapped in [=MaloMyotismon=]'s LotusEaterMachine they're put into illusionary worlds where they all have exactly what they want. They all have rational, sometimes touching and sometimes silly, perfect worlds in mind. Ken's perfect reality, though? Seeing himself as the Digimon Emperor being ''beaten to death by the Digimon he once enslaved''. The kid is in the ''fifth grade''.
36** Ken's parents acknowledging the mistakes they made in raising Sam and Ken and their tearful apology, and promise to be better parents, is equally painful and beautiful. Even more profound, considering that many kids in real life face similar circumstances.
37** The scene where Oikawa is harvesting the Dark Spore to inject it into kids, he's tricked is hard to watch since we see Ken the closest to a total breakdown he had been at the point in the series since Wormmon's death.
38--->'''Ken''': ''(as another of the children is injected with a Dark Spore)'' It's not like you think it'll be. You don't ''want'' to be like me!
39** It doesn't help that he cries out for Davis/Daisuke and Wormmon during said near-breakdown.
40* Oikawa's backstory, especially when he recalls when he was offered his DealWithTheDevil ''and'' how, right before that, he's bawling in despair since his beloved friend Hiroki isn't there with him to see the Digital World they believed in as children.
41-->'''Oikawa:''' ''(holding up a photo of Hiroki to "show" him the portal)'' Do you see it? It's the Digital World we were supposed to visit together! It's beautiful! ''(finally breaks down)'' Why'd you have to do it, Hiroki!? Why'd you have to die and leave me ''[[FriendlessBackground all alone!?]]''
42* [=BlackWarGreymon's=] HeroicSacrifice to save Cody's grandfather after finally realizing the true meaning of friendship in episode 47. [=WarGreymon=] sounded like he was about to cry.
43* Oikawa's death scene, where, for the first time since his possession by Myotismon, he wakes up long enough to see the Digital World finally. Then he finally gets to meet Daitirimon, his partner Digimon just seconds before he dies, dissolving into energy and using that to heal the damage Myotismon did. Both Cody's plea for him to hang on, and his partner Digimon's line "Are you leaving now? But we've only just met!" are particularly effective. Poor Daitirimon disappears seconds later.
44** And even worse, according to [[WordOfGod Hiroyuki Kakudou]], if a human dies, his Digimon also dies, so Datirimon dies shortly after Oikawa's death.
45* Mummymon's VillainousBreakdown following Arukenimon's death at the hand of [=MaloMyotismon=]. It's hard to feel sorry for a villain, even if they are part of the resident TeamRocket squad, but to see his emotional meltdown and subsequent death as well makes you really feel sorry for him.
46** Although she's not a very sympathetic character, Arukenimon's death is nonetheless [[NightmareFuel painfully hard to watch]]. Just the look in her eyes as she pleads not to die is enough to induce tears of pain, especially considering that Mummymon, who's usually TheDitz, feebly tries to attack [=MaloMyotismon=] and fails. Especially considering [[NightmareFuel having Arukenimon think bad thoughts on her possible death]].
47** To compare, imagine James watching Jessie be tortured to death by Giovanni...after she ''hand-delivered'' him a Pokémon he wanted, and then being brutally murdered himself when he tries to avenge her. It's painful and heartbreaking.
48* [[LotusEaterMachine The illusions]] T.K. and Cody had in the series finale, as their deepest desires are impossible to ever come true. Cody just wants to be with his dad and show him the Digital World, while T.K. wants his family reunited. While Kari and Ken got what they wanted eventually, Cody and T.K. have to cope with the fact that their own dreams couldn't be reality; although Matt and T.K.'s parents ''are'' [[AmicableExes on civil terms]], they don't seem to want to get remarried and live together like he wants.
49* Wormmon's ImageSong, "The Future You Dreamed Of, The Future I Dreamed Of."
50* After Wizardmon's ghost comes back, Gatomon tries to touch his hand, but they can't, and they're visibly heartbroken over it as Wizardmon floats away. Then Gatomon thanks Wizardmon for the new life he allowed her to have and promises it wouldn't be in vain. Even the other [=DigiDestined=] are saddened by it, Kari moreso when she comforts her.
51** ''Her damn face when she realizes they can't touch hands''. And Wizardmon's reaction? He looks at his hands, and with such a ''broken tone'' in his voice, can only say, "I'm sorry."
52** A small detail, but Kari is carrying flowers during this whole moment, it's especially noticeable after she comforts Gatomon. Seeing the thoughtful and kind person that she is, she probably bought those flowers in remembrance of their fallen friend.
53** Oh, most ''definitely...'' Especially when he and Gatomon try to hold hands. Her hand passes right through his...he looks sad, and whispers "I'm sorry," before vanishing, leaving her and Kari in tears. The new [=DigiDestined=] ask who that was, because they, of course, have no clue.
54--->'''Gatomon:''' ...A friend.
55** What's worse, [[AllThereInTheManual knowing the series' lore]] means knowing that due to dying in the Human World, Wizardmon can ''never'' be reborn. He's trapped as an intangible specter forever.
56* In the "[[Manga/DigimonVTamer01 Double Tamer]]" crossover, there's something ''extremely'' depressing about the fact that Daisuke believes that no one would care or miss him if he never went home. He is shown to legitimately believe that his teammates don't want him around and that he has absolutely no purpose on the team. Compounding this is that since the story is set between the Kaiser's fall and Ken becoming a SixthRanger, the audience could make the unpleasant leap that Ken might have succeeded in his [[DrivenToSuicide suicidal attempt to destroy his former base]] since Daisuke wouldn't have been around [[InterruptedSuicide to stop him]] and the rest of the kids might not have been bothered. This is something we ''hardly ever get'' in the show proper, so the fact that Daisuke's only allowed to express these kinds of feelings in a debatably-canon crossover becomes this by itself.
57* Yolei's utter horror when [=LadyDevimon=] is killed. Yes, it was a necessary evil, and it saved her life -- but that is still a sixth grader witnessing a friend killing something. It's not unlike a child seeing an animal being killed in front of them.
58-->'''Yolei:''' You...vaporized her.
59** It also highlights just how ''easy'' the 02 kids have had it up until that point. For them, they've either been freeing Digimon from Control Spires or destroying artificial Digimon like Kimeramon or the Control Spire Digimon. The original kids ''didn't.'' They were fighting full on Digimon ''and killing them'' near their entire careers as [=DigiDestined=]. It makes it clear that despite being the same friendly people they were in ''Adventure'', the [=DigiDestined=] were hardened by the forces of evil forcing them to.
60** Silphymon also feels awful about having to kill [=LadyDevimon=], but realizes it was the right thing to do.
61--->'''Silphymon:''' [[ApologeticAttacker You have to understand, I didn't have a choice. You were in great danger]].
62* After Paildramon's debut, Ken is the only one of the four parties involved who's not happy and thrilled about it. First, when two Digimon fuse, their partners' hearts become synced as well, and Ken truly believes he just doesn't deserve to have that bond with Davis or anyone else after everything he did. Second, he's been so lonely and has such little experience with healthy relationships that he's jealous his Digimon partner fused with another, believing this means he now means less to his partner. The poor kid can't even enjoy something that should be nothing but positive.

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