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* ''VisualNovel/DokiDokiLiteratureClub'' does this, as many other tropes, in a weird meta way that can't be discussed without serious late-game spoilers. [[spoiler: Monika is revealed to be in love with the player. Not the PlayerCharacter like the other romanceable characters who lack MediumAwareness, but the actual player. And they can't be together for the rather heavy reason that she's in the game and the player is in reality. Now, obviously whether this qualifies depends on the player feeling the same way -- but, perhaps due to the way that Monika's confession of unconditional love hits after the game's MindScrew and [[TheFourthWallWillNotProtectYou shattering of the fourth wall]], quite a lot of players do reciprocate, experiencing serious LongingForFictionland. There's a whole [[VisualNovel/MonikaAfterStory fanmade mod]] bigger than the original game dedicated to just talking to and virtually dating Monika.]]
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* Some series from ''VisualNovel/ChoicesStoriesYouPlay'' has this theme.
** ''VisualNovel/ItLives'': Both books can have this if either you or your love interests (except [[PlotArmor Connor Green]]) dies while the other survives.
** ''VisualNovel/DesireAndDecorum'' has the protagonist's parents, Vincent and Mary, who were briefly married, but forced to annul due to being from different social classes. They die separately from illness by the end of Book 1.
** ''VisualNovel/WithEveryHeartbeat'' has Sage Woods and Dakota Winchester, whose relationship is already frowned upon on thanks to the latter being diagnosed with cancer. He/she inevitably dies, leaving the protagonist alone by the end of the book.
** ''VisualNovel/KissOfDeath'' has Diamond Wolfe and Victor(ia) Flint in a mobster parody of Theatre/RomeoAndJuliet. [[spoiler:Unlike the rest of the above-mentioned series, they ultimately live HappilyEverAfter]].
** ''VisualNovel/ItLives'': Both books can have this if either you or your love interests (except [[PlotArmor Connor Green]]) dies while the other survives.
** ''VisualNovel/DesireAndDecorum'' has the protagonist's parents, Vincent and Mary, who were briefly married, but forced to annul due to being from different social classes. They die separately from illness by the end of Book 1.
** ''VisualNovel/WithEveryHeartbeat'' has Sage Woods and Dakota Winchester, whose relationship is already frowned upon on thanks to the latter being diagnosed with cancer. He/she inevitably dies, leaving the protagonist alone by the end of the book.
** ''VisualNovel/KissOfDeath'' has Diamond Wolfe and Victor(ia) Flint in a mobster parody of Theatre/RomeoAndJuliet. [[spoiler:Unlike the rest of the above-mentioned series, they ultimately live HappilyEverAfter]].
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* ''VisualNovel/AmnesiaMemories'' pulls all the stops in Joker World to portray the heroine's relationship with Ukyo as this. Uyko [[BeCarefulWhatYouWishFor wished for the heroine's fate of death to be changed]], so that the two of them could be together again, and Lord Nhil allowed him to time travel and go to parallel universes, where the heroine was alive. But things always kept them apart, and her simultaneous existence next to Ukyo is seen as a universal anomaly, leading to the universe to [[EverythingIsTryingToKillYou throw everything at the heroine to kill her]] and fix this mistake. And if she manages to live past her original death date, the universe focuses on Ukyo. Naturally, the [[HappyEnding Good Ending]] for Joker World involves the two of them to overcome this fate, both surviving to the end of August and being happy.
* Tomoya and Tomoyo come very close to this in ''VisualNovel/{{Clannad}}'' if the player goes down Tomoyo's route. The latter is a former delinquent who's cleaned up her image and eventually becomes student council president, the former is still a delinquent and is seen as a problem child by everyone who isn't close to him. [[spoiler:The other members of the student council eventually badger Tomoya into breaking up with Tomoyo by convincing him that he's only holding her back, though eventually they get back together after graduation.]]
* Saint-Germain and Cardia from ''VisualNovel/CodeRealize''. One is a [[spoiler:homunculus created to harbor a Philosopher's Stone until it has matured.]] The other is [[spoiler:an immortal member of The Apostles of Idea, a group dedicated to steering humanity down the path towards salvation.]] [[spoiler:In Idea's eyes, Cardia is a deviation from this path and Saint-Germain is given the order to kill her. Unfortunately, he didn't count on [[SpannerInTheWorks falling in love with her]] before he could do the deed. He has multiple chances to kill her in the common route, but doesn't, and hesitates to kill her in his main route, which leads to Cardia escaping to safety. In the end, he decides that the only way to guarantee her safety is to destroy every member of the Apostles of Idea, an act that will result in his immortality being taken from him and him dying. Cardia rejects this plan, and bargains with the leader of Idea, Omnibus, for Saint-Germain's life at the cost of her destroying her Horologium and dying afterwards. It's only thanks to some serious pleading, a little help from one of the surviving Apostles, and just a hint of proving Omnibus' predictions can be wrong by [[MakesSenseInContext defeating Guinevere]] that they're allowed a hard earned happy ending together.]]
* ''Franchise/{{Danganronpa}}'':
** ''VisualNovel/Danganronpa2GoodbyeDespair'':
*** Fuyuhiko Kuzuryu and [[spoiler:Peko Pekoyama]] may be this trope. (Komaeda believes they are, but it's [[RuleOfDrama deliberately left ambiguous]].) He will never, ever know if she really loves him or is just [[ChildSoldiers conditioned]] to, since she was raised to be his bodyguard, and just as they're in the middle of figuring it out, [[spoiler:she tries a ThanatosGambit for him and it fails, getting herself killed ''and'' him [[EyeScream mutilated]].]] Worsening the trope is that they're both willing to die to protect the other, and in the sort of situation where they might well have to. [[spoiler:It does get better, since Peko (and any other killed person other than Nanami, an ArtificialHuman modeled after the ''already'' dead Nanami who was mentioned above) died in a virtual world created by the Neo World Program, and by the time of ''Super Danganronpa 2.5'' and ''Anime/DanganRonpa3'', she wakes up and she and Kuzuryu are closer than ever.]]
*** Sonia Nevermind and [[spoiler:Gundham Tanaka]]. Just like [[spoiler:Peko above, when Gundham is revealed as Case 4's blackened, Sonia cannot believe it, and demands Monokuma spare him. She vows to carry on his will by taking care of his hamsters, and takes his last words of "Live no matter what!" to heart. Just like Peko and Fuyuhiko above, this does get better as Tanaka wakes up in ''Anime/DanganRonpa3'' Sonia and Gundham are close as can be.]]
*** Akane Owari and [[spoiler:Nekomaru Nidai]]. Though [[spoiler:Nekomaru dies one case prior to his actual death, Monokuma brings him back as a robot which Gundham fights to the death, and ends up killing, thus both Sonia and Akane lose their significant other in the ''exact same case''. As if that wasn't bad enough, Akane is relentless in trying to figure out who killed her "Coach". Yes, three of the five survivors of Goodbye Despair (at least until the 3 anime where everyone wakes up, have all lost someone special to them, four if you count Hajime and Chiaki as a couple.]]
** Then we get to ''VisualNovel/DanganronpaV3KillingHarmony'' and it has no less than three examples, one of which is at first one sided.
*** First goes to [[spoiler:Kaede Akamatsu and Shuichi Saihara]]. A rare instance in the person who dies is [[spoiler:a DecoyProtagonist]] The two are practically inseperable throughout Chapter 1, and even when [[spoiler:Shuichi accuses Kaede of murdering Rantaro Amami, he can barely keep himself together.]]
*** Second is Maki Harukawa and [[spoiler:Kaito Momota]] who are pushed as creator Kazuichi Kodaka's favourite ship in the whole game. Just like most of the above, [[spoiler:Kaito is revealed to be a blackened, which Maki desperately tries to deny, and goes out in a blaze of glory, being the first and so far only, blackened to not die by the execution, but rather the terminal illness he was given by the real mastermind [[BigBad Tsumugi Shirogane]]. Despite this taking longer than previous ships to get going, within the third chapter, [[spoiler:Kaito invites Maki, who he affectionately calls "Maki Roll" to join him and Shuichi in training every night.]] When the mastermind reveals that [[spoiler:Maki and Kaito were ''intentionally'' written as a tragic couple. Maki GoesMadFromTheRevelation.]]
*** The originally one-sided [[DoesNotLikeMen Tenko Chabashira]] and [[CuteWitch Himiko Yumeno]]. [[spoiler:While exactly how much of a couple they are is debatable, it's clear from Tenko's death that Himiko misses her like a lover would miss her deceased boyfriend. When asked, Kodaka gave a ShrugOfGod, showing he does feel they were intended to be a couple, but it's mostly subtext. At first, Himiko hated being gushed over by Tenko, but when she is murdered by Korekiyo Shinguji, Himiko breaks down, and ignores the fact her other best friend died too, and says she'll cast a death spell on anyone who calls Tenko's death meaningless, making it clear she thought of her as more than a friend, she just CannotSpitItOut. Unlike the previous Goodbye Despair examples, none of those who are killed come back to life, making them more straight examples.]]
* ''VisualNovel/FateStayNight'' has Shirou and Saber become this at the end of the ''Fate'' route. After they win the Holy Grail War and destroy the Grail, Saber is forced to return to the moment she died back in the aftermath of the Battle of Camlann, but not before they tell the other that they love them. As Shirou's life returns to normal and Saber dies peacefully, Shirou continues to move forward with his life. The UpdatedReRelease, ''Realta Nua'', adds in an [[OmegaEnding epilogue]], where [[spoiler:Shirou and Saber are given the chance by Merlin to reunite in Avalon as long as Shirou endlessly pursues a way to reach Saber and Saber endlessly waits for Shirou to come back to her. It takes an [[TimeAbyss eternity of struggle and hardship]], but [[EarnYourHappyEnding Shirou eventually succeeds]].]]
* ''VisualNovel/HashihimeOfTheOldBookTown'' [[spoiler:Tamamori and Minakami]] are this, they have loved each other in [[ReincarnationRomance countless past lives]] but never managed to be together, while in their current incarnations [[spoiler:only Minakami is aware of their common past, and he resigned himself to a one-sided love because of the shame he feels for his own homosexuality and the price he had to pay as a child to save Tamamori using [[TimeTravelRomance his time traveling powers]]. It takes Tamamori [[GroundhogDayLoop many loops]] and the help of his future self to realize what he actually has been feeling for Minakami since he was a child was romantic love.]]
* ''VisualNovel/HatofulBoyfriend''
** Anghel claims that he and Hiyoko were star-crossed lovers in a previous life. [[spoiler:If his route is to be trusted, he's almost surely telling the truth.]]
** [[spoiler:Nageki and Hiyoko become this if his path is completed. Nageki [[AscendToAHigherPlaneOfExistence fades away]], due to him realising that he loves Hiyoko, and tells her that as he loves her as he disappears]].
* ''VisualNovel/HigurashiWhenTheyCry'' has Shion Sonozaki and Satoshi Houjou. The latter's family became outcasts after they accepted money from the government to leave the village where a dam was to be built (while the rest of the village fought against it). When Shion fell in love with him, her family was a bit... angry about it. "Rip off three of your fingernails in repentance in a torture chamber" angry. To the point Shion thinks for a long time [[spoiler:that her family had the boy killed]], although she was wrong about that.
* ''VisualNovel/KatawaShoujo'':
** Hisao Nakai and [[spoiler:Lilly Satou]], if the player get their BadEnding and [[spoiler:Lilly goes back to Scotland with her family, never to return. The Good Ending is all about Hisao deciding to ScrewDestiny and taking a RaceForYourLove to [[EarnYourHappyEnding stop this at the last moment]].]]
** Also Hisao and [[spoiler:Rin Tezuka]], ''especially'' in the Neutral Ending where she leaves Yamaku to go to Tokyo, fully knowing that she'll become [[spoiler:a great artist]] but at the cost of [[DespairEventHorizon destroying herself mentally.]] Her last scene has her [[spoiler:begging Hisao to forget about her, and they share a last hug under the rain before she abandons him and her former life forever.]]
* Discussed in ''VisualNovel/{{Melody}}''. At one point, the protagonist has the option of taking the title character to see a music-themed movie. When they speculate afterwards on whether the main couple will stay together after the story ends, Melody is convinced that they won’t.
* ''VisualNovel/ShallWeDateNinjaShadow'' dabbles into it twice:
** The PlayerCharacter Saori can enter a relationship with Toru [[spoiler:Nakagawa]]. She's a member of a VigilanteMan group devoted to protect the city of Nagasaki, whereas he's an AntiVillain determined to violently overthrow the corrupt and old-fashioned Tokugawa Shogunate [[spoiler:''and'' is the rebellious brother of Saori's boss, Makoto]]; as such she prioritizes her loyalties to the group and to Nagasaki over their love, no matter how much it hurts the two of them, and Toru is well-aware of her determination - if not even a little proud, since it tells him [[AmazonChaser how strong]] [[PluckyGirl Saori is]]... [[spoiler:It's ultimately subverted: while Toru is captured, judged and exiled, both of his endings have him and Saori [[EarnYourHappyEnding ultimately reunited in one way or another]].]]
** The other prospect SCL deal will take place in the path of Toru's best friend and companion, Tsubaki Kusunoki. Tsubaki is a BadassBookworm who grew deeply bitter [[spoiler:due to being [[HalfBreedDiscrimination half-Japanese/half-Dutch]] ''and'' [[SonOfAWhore the son of]] a HighClassCallGirl]], and as such he also views the Shogunate as ineffectual and corrupt; he plans to [[spoiler:personally assassinate the Tokugawa Shogun]] and launch Japan in a new era from then onwards. Saori, logically, loves him deeply but disagrees with that, since she wants the Shogunate to change but '''not''' through violence [[spoiler:and magnicide]]; they discuss their positions several times, but in the end they can't reach an agreement. [[spoiler:Subverted, too: Saori and the Vigilantes manage to ''barely'' stop Tsubaki from killing the Shogun, said Shogun turns out to be a ReasonableAuthorityFigure that pardons Tsubaki in exchange of having him work with the Vigilantes, and [[LoveRedeems Tsubaki gains his faith on people back AND stays with Saori]].]]
* Arcueid and Shiki from ''VisualNovel/{{Tsukihime}}''. One is an immortal vampire princess and the other is a vampire-hunting human who ''kills her'' in their first meeting ([[ResurrectiveImmortality she got better]]).
* Haruki and Kazusa in ''VisualNovel/WhiteAlbum2'', particularly during the ''Introductory Chapter'' (the part which got adapted into an anime). Haruki is a normal, if friendly and helpful guy, while Kazusa is a budding pianist with potentially world-class talent. The climax of the anime hammers home the fact that, in any other circumstance, it would still be impossible for them to be together. Which is exactly what happens in the end: Kazusa leaves to further develop her craft in Europe, and leaves Haruki behind in Japan.
* ''VisualNovel/ZeroEscape'' has Akane and Junpei. The classical ChildhoodFriendRomance, except [[spoiler:Akane is TheChessmaster Zero I for much of the series, and she has plans for world salvation that ''specifically must not'' include Junpei accompanying her]]. In the final game, ''[[VisualNovel/ZeroTimeDilemma Zero-Time Dilemma]]'', [[spoiler:this is eventually [[SubvertedTrope subverted]] by creating a timeline where [[HappilyEverAfter they can marry]]]]. Ironically, [[spoiler:they have ''[[BigBad Delta]]'' to thank for this, as his plan [[TheExtremistWasRight was to create a world where the characters could live happy lives]]]].
* Tomoya and Tomoyo come very close to this in ''VisualNovel/{{Clannad}}'' if the player goes down Tomoyo's route. The latter is a former delinquent who's cleaned up her image and eventually becomes student council president, the former is still a delinquent and is seen as a problem child by everyone who isn't close to him. [[spoiler:The other members of the student council eventually badger Tomoya into breaking up with Tomoyo by convincing him that he's only holding her back, though eventually they get back together after graduation.]]
* Saint-Germain and Cardia from ''VisualNovel/CodeRealize''. One is a [[spoiler:homunculus created to harbor a Philosopher's Stone until it has matured.]] The other is [[spoiler:an immortal member of The Apostles of Idea, a group dedicated to steering humanity down the path towards salvation.]] [[spoiler:In Idea's eyes, Cardia is a deviation from this path and Saint-Germain is given the order to kill her. Unfortunately, he didn't count on [[SpannerInTheWorks falling in love with her]] before he could do the deed. He has multiple chances to kill her in the common route, but doesn't, and hesitates to kill her in his main route, which leads to Cardia escaping to safety. In the end, he decides that the only way to guarantee her safety is to destroy every member of the Apostles of Idea, an act that will result in his immortality being taken from him and him dying. Cardia rejects this plan, and bargains with the leader of Idea, Omnibus, for Saint-Germain's life at the cost of her destroying her Horologium and dying afterwards. It's only thanks to some serious pleading, a little help from one of the surviving Apostles, and just a hint of proving Omnibus' predictions can be wrong by [[MakesSenseInContext defeating Guinevere]] that they're allowed a hard earned happy ending together.]]
* ''Franchise/{{Danganronpa}}'':
** ''VisualNovel/Danganronpa2GoodbyeDespair'':
*** Fuyuhiko Kuzuryu and [[spoiler:Peko Pekoyama]] may be this trope. (Komaeda believes they are, but it's [[RuleOfDrama deliberately left ambiguous]].) He will never, ever know if she really loves him or is just [[ChildSoldiers conditioned]] to, since she was raised to be his bodyguard, and just as they're in the middle of figuring it out, [[spoiler:she tries a ThanatosGambit for him and it fails, getting herself killed ''and'' him [[EyeScream mutilated]].]] Worsening the trope is that they're both willing to die to protect the other, and in the sort of situation where they might well have to. [[spoiler:It does get better, since Peko (and any other killed person other than Nanami, an ArtificialHuman modeled after the ''already'' dead Nanami who was mentioned above) died in a virtual world created by the Neo World Program, and by the time of ''Super Danganronpa 2.5'' and ''Anime/DanganRonpa3'', she wakes up and she and Kuzuryu are closer than ever.]]
*** Sonia Nevermind and [[spoiler:Gundham Tanaka]]. Just like [[spoiler:Peko above, when Gundham is revealed as Case 4's blackened, Sonia cannot believe it, and demands Monokuma spare him. She vows to carry on his will by taking care of his hamsters, and takes his last words of "Live no matter what!" to heart. Just like Peko and Fuyuhiko above, this does get better as Tanaka wakes up in ''Anime/DanganRonpa3'' Sonia and Gundham are close as can be.]]
*** Akane Owari and [[spoiler:Nekomaru Nidai]]. Though [[spoiler:Nekomaru dies one case prior to his actual death, Monokuma brings him back as a robot which Gundham fights to the death, and ends up killing, thus both Sonia and Akane lose their significant other in the ''exact same case''. As if that wasn't bad enough, Akane is relentless in trying to figure out who killed her "Coach". Yes, three of the five survivors of Goodbye Despair (at least until the 3 anime where everyone wakes up, have all lost someone special to them, four if you count Hajime and Chiaki as a couple.]]
** Then we get to ''VisualNovel/DanganronpaV3KillingHarmony'' and it has no less than three examples, one of which is at first one sided.
*** First goes to [[spoiler:Kaede Akamatsu and Shuichi Saihara]]. A rare instance in the person who dies is [[spoiler:a DecoyProtagonist]] The two are practically inseperable throughout Chapter 1, and even when [[spoiler:Shuichi accuses Kaede of murdering Rantaro Amami, he can barely keep himself together.]]
*** Second is Maki Harukawa and [[spoiler:Kaito Momota]] who are pushed as creator Kazuichi Kodaka's favourite ship in the whole game. Just like most of the above, [[spoiler:Kaito is revealed to be a blackened, which Maki desperately tries to deny, and goes out in a blaze of glory, being the first and so far only, blackened to not die by the execution, but rather the terminal illness he was given by the real mastermind [[BigBad Tsumugi Shirogane]]. Despite this taking longer than previous ships to get going, within the third chapter, [[spoiler:Kaito invites Maki, who he affectionately calls "Maki Roll" to join him and Shuichi in training every night.]] When the mastermind reveals that [[spoiler:Maki and Kaito were ''intentionally'' written as a tragic couple. Maki GoesMadFromTheRevelation.]]
*** The originally one-sided [[DoesNotLikeMen Tenko Chabashira]] and [[CuteWitch Himiko Yumeno]]. [[spoiler:While exactly how much of a couple they are is debatable, it's clear from Tenko's death that Himiko misses her like a lover would miss her deceased boyfriend. When asked, Kodaka gave a ShrugOfGod, showing he does feel they were intended to be a couple, but it's mostly subtext. At first, Himiko hated being gushed over by Tenko, but when she is murdered by Korekiyo Shinguji, Himiko breaks down, and ignores the fact her other best friend died too, and says she'll cast a death spell on anyone who calls Tenko's death meaningless, making it clear she thought of her as more than a friend, she just CannotSpitItOut. Unlike the previous Goodbye Despair examples, none of those who are killed come back to life, making them more straight examples.]]
* ''VisualNovel/FateStayNight'' has Shirou and Saber become this at the end of the ''Fate'' route. After they win the Holy Grail War and destroy the Grail, Saber is forced to return to the moment she died back in the aftermath of the Battle of Camlann, but not before they tell the other that they love them. As Shirou's life returns to normal and Saber dies peacefully, Shirou continues to move forward with his life. The UpdatedReRelease, ''Realta Nua'', adds in an [[OmegaEnding epilogue]], where [[spoiler:Shirou and Saber are given the chance by Merlin to reunite in Avalon as long as Shirou endlessly pursues a way to reach Saber and Saber endlessly waits for Shirou to come back to her. It takes an [[TimeAbyss eternity of struggle and hardship]], but [[EarnYourHappyEnding Shirou eventually succeeds]].]]
* ''VisualNovel/HashihimeOfTheOldBookTown'' [[spoiler:Tamamori and Minakami]] are this, they have loved each other in [[ReincarnationRomance countless past lives]] but never managed to be together, while in their current incarnations [[spoiler:only Minakami is aware of their common past, and he resigned himself to a one-sided love because of the shame he feels for his own homosexuality and the price he had to pay as a child to save Tamamori using [[TimeTravelRomance his time traveling powers]]. It takes Tamamori [[GroundhogDayLoop many loops]] and the help of his future self to realize what he actually has been feeling for Minakami since he was a child was romantic love.]]
* ''VisualNovel/HatofulBoyfriend''
** Anghel claims that he and Hiyoko were star-crossed lovers in a previous life. [[spoiler:If his route is to be trusted, he's almost surely telling the truth.]]
** [[spoiler:Nageki and Hiyoko become this if his path is completed. Nageki [[AscendToAHigherPlaneOfExistence fades away]], due to him realising that he loves Hiyoko, and tells her that as he loves her as he disappears]].
* ''VisualNovel/HigurashiWhenTheyCry'' has Shion Sonozaki and Satoshi Houjou. The latter's family became outcasts after they accepted money from the government to leave the village where a dam was to be built (while the rest of the village fought against it). When Shion fell in love with him, her family was a bit... angry about it. "Rip off three of your fingernails in repentance in a torture chamber" angry. To the point Shion thinks for a long time [[spoiler:that her family had the boy killed]], although she was wrong about that.
* ''VisualNovel/KatawaShoujo'':
** Hisao Nakai and [[spoiler:Lilly Satou]], if the player get their BadEnding and [[spoiler:Lilly goes back to Scotland with her family, never to return. The Good Ending is all about Hisao deciding to ScrewDestiny and taking a RaceForYourLove to [[EarnYourHappyEnding stop this at the last moment]].]]
** Also Hisao and [[spoiler:Rin Tezuka]], ''especially'' in the Neutral Ending where she leaves Yamaku to go to Tokyo, fully knowing that she'll become [[spoiler:a great artist]] but at the cost of [[DespairEventHorizon destroying herself mentally.]] Her last scene has her [[spoiler:begging Hisao to forget about her, and they share a last hug under the rain before she abandons him and her former life forever.]]
* Discussed in ''VisualNovel/{{Melody}}''. At one point, the protagonist has the option of taking the title character to see a music-themed movie. When they speculate afterwards on whether the main couple will stay together after the story ends, Melody is convinced that they won’t.
* ''VisualNovel/ShallWeDateNinjaShadow'' dabbles into it twice:
** The PlayerCharacter Saori can enter a relationship with Toru [[spoiler:Nakagawa]]. She's a member of a VigilanteMan group devoted to protect the city of Nagasaki, whereas he's an AntiVillain determined to violently overthrow the corrupt and old-fashioned Tokugawa Shogunate [[spoiler:''and'' is the rebellious brother of Saori's boss, Makoto]]; as such she prioritizes her loyalties to the group and to Nagasaki over their love, no matter how much it hurts the two of them, and Toru is well-aware of her determination - if not even a little proud, since it tells him [[AmazonChaser how strong]] [[PluckyGirl Saori is]]... [[spoiler:It's ultimately subverted: while Toru is captured, judged and exiled, both of his endings have him and Saori [[EarnYourHappyEnding ultimately reunited in one way or another]].]]
** The other prospect SCL deal will take place in the path of Toru's best friend and companion, Tsubaki Kusunoki. Tsubaki is a BadassBookworm who grew deeply bitter [[spoiler:due to being [[HalfBreedDiscrimination half-Japanese/half-Dutch]] ''and'' [[SonOfAWhore the son of]] a HighClassCallGirl]], and as such he also views the Shogunate as ineffectual and corrupt; he plans to [[spoiler:personally assassinate the Tokugawa Shogun]] and launch Japan in a new era from then onwards. Saori, logically, loves him deeply but disagrees with that, since she wants the Shogunate to change but '''not''' through violence [[spoiler:and magnicide]]; they discuss their positions several times, but in the end they can't reach an agreement. [[spoiler:Subverted, too: Saori and the Vigilantes manage to ''barely'' stop Tsubaki from killing the Shogun, said Shogun turns out to be a ReasonableAuthorityFigure that pardons Tsubaki in exchange of having him work with the Vigilantes, and [[LoveRedeems Tsubaki gains his faith on people back AND stays with Saori]].]]
* Arcueid and Shiki from ''VisualNovel/{{Tsukihime}}''. One is an immortal vampire princess and the other is a vampire-hunting human who ''kills her'' in their first meeting ([[ResurrectiveImmortality she got better]]).
* Haruki and Kazusa in ''VisualNovel/WhiteAlbum2'', particularly during the ''Introductory Chapter'' (the part which got adapted into an anime). Haruki is a normal, if friendly and helpful guy, while Kazusa is a budding pianist with potentially world-class talent. The climax of the anime hammers home the fact that, in any other circumstance, it would still be impossible for them to be together. Which is exactly what happens in the end: Kazusa leaves to further develop her craft in Europe, and leaves Haruki behind in Japan.
* ''VisualNovel/ZeroEscape'' has Akane and Junpei. The classical ChildhoodFriendRomance, except [[spoiler:Akane is TheChessmaster Zero I for much of the series, and she has plans for world salvation that ''specifically must not'' include Junpei accompanying her]]. In the final game, ''[[VisualNovel/ZeroTimeDilemma Zero-Time Dilemma]]'', [[spoiler:this is eventually [[SubvertedTrope subverted]] by creating a timeline where [[HappilyEverAfter they can marry]]]]. Ironically, [[spoiler:they have ''[[BigBad Delta]]'' to thank for this, as his plan [[TheExtremistWasRight was to create a world where the characters could live happy lives]]]].
