History Tearjerker / BakeMonogatari

** When they finally manage to escort her "home" at the conclusion of her arc, while it doubles somewhat as a [[SugarWiki/HeartwarmingMoments Heartwarming Moment]], there's something quite sad about seeing her bawl, with her awkward oversized backpack and pitiful band-aid, alone in front of her long-destroyed home, before running off into the bright afterlife.

--> ''Kaiki'': They say money talks even in hell. Since I don't have money saved up, I felt really glad from the bottom of my heart that I was able to earn some pocket change at the end.(In context, the "pocket change" is referencing good actions, i.e. helping people.)

* The end of the second episode, where Hitagi admits [[spoiler:that she wonders if maybe she had given into the scammer cult's leader when he sexually assaulted her, her family would still be together]]. Ouch.
** Also, earlier in the same episode, [[spoiler: immediately after Hitagi has her weight returned to her. Watching her break down and cry after getting used to her stoic characterization can be quite jarring to the viewer.]]
* In a severe case of MoodWhiplash, Koyomi goes from teasing Mayoi to nearly breaking down crying when he finds out [[spoiler:that she's been DeadAllAlong and is in fact that lost cow, and the best way for him to get rid of her is to abandon her]].
* The last episode. When Araragi realizes [[spoiler: that when Oshino told him "I'm going to leave this city one day", that in fact was his way of saying goodbye, because he doesn't like formally saying goodbye.]] Whilst we already know Oshino is a JerkWithAHeartOfGold, this shows that he is incredibly soft when it comes to goodbyes.
* Hanekawa at the end of the Tsubasa Tiger arc [[spoiler:finally tells Araragi how she feels about him. Araragi gently rejects her proposal, something she knows already, and allows herself to feel heartbreak and cry.]]
* Episode 10 of the second season is a series of {{gut punch}}es. [[spoiler:1) Alternate!Black Hanekawa killed Alternate!Koyomi. 2) Alternate!Kissshot turns the entire town into zombies out of despair. 3) Oshino, Kaiki and Kagenui went off to face Kissshot in what was most likely a SuicideMission and are probably dead by the time Koyomi gets [[InfoDump the letter he wrote]] and gave to Alternate!Mayoi. And then finally 4) [[TragicVillain Kissshot herself shows up.]]]] It's just a generally depressing episode [[spoiler:[[EarnYourHappyEnding that thankfully ends happy]]]]. It's also kind of touching that in this world Araragi also ended up being with Hitagi.
* The last episode of Shinobu Time, where [[spoiler:Mayoi Hachikuji disappears for good.]] This episode becomes even more heart-wrenching, if you have watched [[spoiler:''Anime/AngelBeats'' before this episode and realize, that [[Creator/HiroshiKamiya Koyomi's]] and Mayoi's last conversation is very reminding of [[TearJerker one of the last scenes]] of ''Angel Beats!'']]
* Episode 26 of the second season: [[spoiler:[[KarmaHoudiniWarranty Kaiki gets beaten by one of the kids he gave the snake curses to]].]] Normally this wouldn't warrant a TearJerker response, but the audience had just spent the last arc warming up to the character. Even worse when one considers [[NoGoodDeedGoesUnpunished the foreshadowing Gaen mentioned.]]
** It's strongly implied that [[spoiler: Kaiki was not only beaten, but [[HoistByHisOwnPetard killed by his victim]]]] which does nothing to lighten the scene ([[spoiler: he didn't actually die]]), and the season finishes off with an emotional WhamLine:
--> [[spoiler: ''Kaiki'': They say money talks even in hell. Since I don't have money saved up, I felt really glad from the bottom of my heart that I was able to earn some pocket change at the end.]](In context, the [[spoiler: "pocket change"]] is referencing good actions, i.e. helping people.)

* [[spoiler: Shinobu's heartbreaking final farewell to her first beloved servant Seishirou, following the latter's defeat against Araragi]] in ''Owarimonogatari's'' ''Shinobu Mail'' arc. This scene alone marks one of the very few times where [[spoiler: Shinobu actually ''cries'', bidding him goodbye and saying how much she loved and missed him as she finally laid him to rest by her own hands. To make things even sadder in hindsight, it was Seishirou's death that triggered Kiss Shot's DeathSeeker tendencies before and during the events of ''Kizumonogatari'', so seeing him die ''again'' must've been very hard for Shinobu.]]
* Koyomi's confrontation with [[spoiler: Ougi at the end of Owarimonogatari 2nd Season.]]

* [[spoiler: Shinobu's heartbreaking final farewell to her first beloved servant Seishirou, following the latter's defeat against Araragi]] in ''Owarimonogatari's'' ''Shinobu Mail'' arc. This scene alone marks one of the very few times where [[spoiler: Shinobu actually ''cries'', bidding him goodbye and saying how much she loved and missed him as she finally laid him to rest by her own hands. To make things even sadder in hindsight, it was Seishirou's death that triggered Kiss Shot's DeathSeeker tendencies before and during the events of ''Kizumonogatari'', so seeing him die ''again'' must've been very hard for Shinobu.]]

** It's strongly implied that [[spoiler: Kaiki was not only beaten, but [[HoistByHisOwnPetard killed by his victim]]]]which does nothing to lighten the scene([[spoiler: he didn't actually die]]), and the season finishes off with an emotional WhamLine:

* Once you learn about [[JerkassWoobie Sodachi's]] particularly ''horrid'' backstory ([[WorldOfWoobie among others]]) in ''Sodachi Riddle'', you will ''definitely'' understand why [[{{Jerkass}} she is]] [[BrokenBird the way she is]] and why she's so bitterly hateful towards Araragi in the present day.

* [[spoiler: Shinobu's heartbreaking final farewell to her first beloved servant Seishirou, following the latter's defeat against Araragi]] in ''Owarimonogatari''. This scene alone marks one of the very few times where [[spoiler: Shinobu actually ''cries'', bidding him goodbye and saying how much she loved and missed him as she finally laid him to rest by her own hands. To make things even sadder in hindsight, it was Seishirou's death that triggered Kiss Shot's DeathSeeker tendencies before and during the events of ''Kizumonogatari'', so seeing him die ''again'' must've been very hard for Shinobu.]]

--> [[spoiler: ''Kaiki'': They say money talks even in hell. Since I don't have money saved up, I felt really glad from the bottom of my heart that I was able to earn some pocket change at the end.]](In context, the [[spoiler: "pocket change"]] is referencing good actions, i.e. helping people.)

* Episode 10 of the second season is a series of {{gut punch}}es. [[spoiler:1) Alternate!Black Hanekawa killed Alternate!Koyomi. 2) Alternate!Kiss-Shot turns the entire town into zombies out of despair. 3) Oshino, Kaiki and Kagenui went off to face Kiss-Shot in what was most likely a SuicideMission and are probably dead by the time Koyomi gets [[InfoDump the letter he wrote]] and gave to Alternate!Mayoi. And then finally 4) [[TragicVillain Kiss-Shot herself shows up.]]]] It's just a generally depressing episode [[spoiler:[[EarnYourHappyEnding that thankfully ends happy]]]]. It's also kind of touching that in this world Araragi also ended up being with Hitagi.

* The last episode of Shinobu Time, where [[spoiler:Mayoi Hachikuji disappears for good.]]
** This episode becomes even more heart-wrenching, if you have watched [[spoiler: AngelBeats before this episode and realize, that [[Creator/HiroshiKamiya Koyomi's]] and Mayoi's last conversation is very reminding of [[TearJerker one of the last scenes]] of AngelBeats.]]

** It's strongly implied that [[spoiler: Kaiki was not only beaten, but [[HoistByHisOwnPetard killed by his victim]]]]which does nothing to lighten the scene, and the season finishes off with an emotional WhamLine:

* Episode 26 of the second season: [[spoiler:[[KarmaHoudiniWarranty Kaiki gets beaten by one of the kids he gave the snake curses to]].]] Normally this wouldn't warrant a TearJerker response, but the audience had just spent the last arc warming up to the character. Even worse when one considers [[NoGoodDeedGoesUnpunished the foreshadowing Gaen mentioned.]]

** Also, earlier in the second episode, [[spoiler: immediately after Hitagi has her weight returned to her. Watching her break down and cry after getting used to her stoic characterization can be quite jarring to the viewer.]]

* Episode 26 of the second season: [[spoiler:[[KarmaHoudiniWarranty Kaiki gets stabbed by one of the kids he gave the snake curses to]].]] Normally this wouldn't warrant a TearJerker response, but the audience had just spent the last arc warming up to the character. Even worse when one considers [[NoGoodDeedGoesUnpunished the foreshadowing Gaen mentioned.]]

** This episode becomes even more heart-wrenching, if you have watched [[spoiler: AngelBeats before this episode and realize, that [[HiroshiKamiya Koyomi`s]] and Mayoi`s last conversation is very reminding of [[TearJerker one of the last scenes]] of AngelBeats.]]

** This episode becomes even more heart-wrenching, if you have watched [[spoiler: AngelBeats before this episode and realize, that [[HiroshiKamiya Koyomi`s]] and Mayoi`s last conversation is very reminding of [[TearJerker one of the last scenes]] of AngelBeats.]]

** This episode becomes even more heart-wrenching, if you have watched [[spoiler: AngelBeats before this episode and realize, that Koyomi`s and Mayoi`s last conversation is very reminding of [[TearJerker one of the last scenes]] of AngelBeats.]]

** This episode becomes even more heart-wrenching, if you have watched [[spoiler: Angel Beats! before this episode and realize, that Koyomi`s and Mayoi`s last conversation is very reminding of [[TearJerker one of the last scenes]] of Angel Beats!]]

* The last episode of Shinobu Time, where [[spoiler:Mayoi Hachikuji disappears for good.]]

* Episode 10 of the second season is a series of {{gut punch}}es. [[spoiler:1) Alternate!Black Hanekawa killed Alternate!Koyomi. 2) Alternate!Kiss-Shot turns the entire town into zombies out of despair. 3) Oshino, Kaiki and Kagenui went off to face Kiss-Shot in what was most likely a SuicideMission and are probably dead by the time Koyomi gets [[InfoDump the letter he wrote]] and gave to Alternate!Mayoi. And then finally 4) [[TragicVillain Kiss-Shot herself shows up.]]]] It's just a generally depressing episode [[spoiler:[[EarnYourHappyEnding that thankfully ends happy]]]].

* The end of the second episode, where Hitagi admits [[spoiler:that she wonders if maybe she had given into the scammer cult's leader when he sexually assaulted her, her family would still be together]]]. Ouch.