History Main / DidNotGetTheGirl

* ''Webcomic/MyImpossibleSoulmate'' opens with Chiaki's crush getting a boyfriend before she could confess.

* In ''WesternAnimation/RankinBassJackFrost,'' the titular sprite is InvisibleToNormals, but hears a beautiful girl named Elisa say that she's "in love with Jack Frost." Taking her at her word, he [[PinocchioSyndrome becomes human]], but will only stay that way if she marries him by the beginning of spring. While she and "Jack Snip" become close, he learns right before the deadline that she's fallen in love with her NewOldFlame, [[KnightInShiningArmor Sir Ravenal]]. He turns back into a sprite just as the pair are HappilyMarried.

* ''Machinima/RedVsBlue'':

Despite the name, this trope can just as easily apply to not getting the ''guy''. Of course, the idea of a person being something to ''get'', like she or he is a possession, can be troubling to ponder.

* DidNotGetTheGirl/LiveActionFilms

[[folder:Anime & Manga]]
* This is played straight in the third act of ''Anime/FiveCentimetersPerSecond'', despite a good taunting/glimmer of hope thrown in for good measure at the end - which doesn't pan out.
* ''Manga/BladeOfTheImmortal'': Rin develops feelings for her bodyguard Manji, but he mostly sees her as a little sister, and the fact that he's immortal makes him reluctant to have a committed relationship with someone he'd inevitably outlive. The two part ways after Rin fulfills her quest for revenge, and the epilogue has Manji meeting Rin's great-granddaughter.
* ''Manga/BlueFlag'': [[spoiler:The penultimate chapter reveals that the main couple of the manga, Kuze and Taichi, broke up two years after they got together and finished high school, in a mutual agreement. They have grown distant due to the awkwardness, though they still share a circle of friends, and Taichi is invited to Kuze's wedding to another man. Taichi himself eventually figures out he's attracted to both men and women, and starts a relationship with his male friend Touma, to whom he has since married]].
* Despite all their UnresolvedSexualTension, the titular character of ''Anime/{{Canaan}}'' and her [[HideYourLesbians friend]] Maria never make the RelationshipUpgrade. Their lives are too different and they go their separate ways.
* The final chapter of ''Ciguatera'' reveals that [[ButtMonkey protagonist Ogino]] eventually broke up with [[UglyGuyHotWife his hot girlfriend Nagumo]], after realizing he has become dependent on her and lacks the maturity to give her a happy life. Nagumo is last shown 9 months pregnant and married to someone else, while Ogino got his act together and found a new love. It's probably for the best and [[HappilyEverAfter they're both shown to be happy]].
* ''Anime/CodeGeass'' had a field day with this trope:
** [[spoiler: Shirley]] died shortly after her AnguishedDeclarationOfLove so she and [[spoiler:Lelouch]] didn't end up together.
** Season 2 also spent a lot of episodes teasing the [[UnresolvedSexualTension sexual tension]] between Lelouch and Kallen. That also came to a halt when Lelouch willingly pushed her away so she wouldn't get involved in his final plan.
** Finally, Lelouch ''also'' didn't end up with C.C. because of his own death. Suzaku also did not get Euphemia; although they were in a relationship briefly, Euphie gets shot by Zero/Lelouch after the SAZ Japan massacre. Given the [[IncestSubtext subtext]], Lelouch did not get Euphie either.
** This also still happens in the movie series. [[spoiler: Shirley doesn't end up with Lelouch under different circumstances, such as living to see ''him'' die as part of his ThanatosGambit, and even after playing a part in bringing him BackFromTheDead, he ultimately goes with C.C. It is implied he's just as sad as she probably is that things didn't turn out as she thought.]]
* In ''Anime/DigimonAdventure'' the kids are really too young to be concerned with dating, but when ''Anime/DigimonAdventure02'' rolls around, [[TheHero Taichi/Tai]] does not end up with childhood friend [[TeamMom Sora]], as she instead hooks up with [[TheLancer Yamato/Matt]].
* ''Anime/FantasticChildren'' fits this perfectly and it's even a large part of the plot. He seems to eventually accept to live with it. The guy she picks is a good guy and all, but it is still a bit of a downer.
* Despite having three potential LoveInterests, the main character of ''Anime/{{FLCL}}'' ends up with no one. It implies that he will end up with [[spoiler:Ninamori]] but only after they're [[spoiler:not kids anymore and are more mature]]. This is averted in the manga, where he ends up with [[spoiler:Haruko]] but he [[spoiler:has to chase after her]].
* The [[Anime/FullmetalAlchemist 2003 anime version]] of ''Manga/FullmetalAlchemist'' ends this way (''twice''): in the TV ending, [[spoiler: Ed is [[TrappedInAnotherWorld trapped in our world]] searching for a way to get back while Winry and Rose are left behind]], and in TheMovie ''Anime/FullmetalAlchemistTheConquerorOfShamballa'' [[spoiler:after finding a way back to Amestris and reuniting with Winry, he realizes that our world needs him more than Amestris and seizes his last chance to return and seals off the portal connecting the two worlds for good, leaving Winry behind yet again]]. The [[TruerToTheText second anime]] unambiguously ends with Ed and Winry together.
* In ''Anime/TheGirlWhoLeaptThroughTime'', [[spoiler:Makoto doesn't get together with Chiaki]], which is especially egregious considering he asked her first and through how much trouble and grief she went through to make it happen. Although it is indicated that they plan to meet again in his time:
-->'''[[spoiler:Chiaki]]:''' I'll be waiting in the future.
-->'''[[spoiler:Makoto]]:''' I'll be right there. I'll run there.
* Punpun spends the entirety of ''Manga/GoodnightPunpun'' pining after his first love, Aiko. They eventually meet again and begin dating in his twenties, however their relationship is unhealthy and the circumstances aren't perfect. [[spoiler:For one, they're on the run from the police for killing Aiko's mother.]] It ultimately ends very poorly as [[spoiler:Aiko ends up [[DrivenToSuicide killing herself]]. Punpun tries to too but [[BungledSuicide survives]], though he loses an eye]].
* The infamous ending to ''Anime/TheGreatMissionToSavePrincessPeach'' has the revelation that [[spoiler:Princess Peach was already engaged to a prince named Haru, which upsets Mario but he [[IWantMyBelovedToBeHappy wishes her good luck regardless]]. Needless to say, said prince was never featured in any ''Franchise/SuperMarioBros'' media again]].
* In ''Anime/JewelpetSunshine'', the protagonist Kanon dates her crush Mikage for several episodes. Then comes TheReveal that [[spoiler:they're siblings]], and Kanon has to forcibly give him up, without a consolation prize.
* ''Series/{{Kikaider}}'', is more a case of [[spoiler:someone [[BreakThemByTalking breaking speeching]] him into walking out on the girl]].
* Inevitable in nearly all installments of ''Anime/KnightHunters'' due to the protagonists being {{Doom Magnet}}s - the few potential love interests who don't end up dead get the ItsNotYouItsMyEnemies treatment. The only exception here is ''Farfarello'', who leaves with his love interest at the end of the Schwarz audio drama to lead a happy, kill-free life.
* ''Franchise/LupinIII'': Lupin's success with the ladies tends to be hit-or-miss. Such as:
** In ''[[Anime/LupinIIIIslandOfAssassins Island of Assassins]]'', he tried hitting on [[BrokenBird Ellen]], though it was mainly just fun 'n games for him, until he learned how she became part of [[MurderInc the Tarantulas.]] She was initially put off by his attempts to flirt with her because she didn't trust him. By the end of the film, her opinion of him had changed, but only so far as thanking him for giving her a brief moment of freedom. [[spoiler: Said with her dying breath]].
** ''[[Anime/LupinIIIThePursuitOfHarimaosTreasure The Pursuit of Harimao's Treasure]]'': From the moment he first sees her, Lupin does his damnedest to woo [[CoolOldGuy Sir Archer's]] granddaughter, Diana. She repeatedly blows off his advances throughout the film; including [[ArmorPiercingSlap belting him]] several times for emphasis. By the end, she agrees to have dinner with him but makes it clear that '''THAT's''' as far as it goes.
* Gender-inverted examples are common in the ''Anime/{{Macross}}'' series:
** ''Anime/SuperDimensionFortressMacross'': At the end of the series, [[TheHero Hikaru Ichijo]] picks Misa Hayase instead of Lynn Minmay. However, Minmay becomes the couple's friend and joins them in the SDF-2 Megaroad-01.
** A similar fate happens to Ranka Lee in the second [[TheMovie Movie]] of ''Anime/MacrossFrontier'', where Alto Saotome declares that he loves Sheryl Nome, but Ranka believes that one day Alto will come back and Sheryl will be awake from the coma. Since the movie is an AlternateContinuity, this is averted in the TV series.
* ''Manga/MakenKi'': By the final chapter (124), Kai is no closer to hooking up with the [[AmazonianBeauty Amazonian]] [[HeroesWantRedheads redhead]], Azuki. Usui doesn't fare any better in his romantic pursuit of [[ElegantGothicLolita Himegami]], who still only regards him as one of her friends.
* ''LightNovel/{{No 6}}'': Shion [[spoiler: did not get the guy or girl: Not only does Nezumi leave him behind when they're done, but Safu, his [[GayOption Het Option]], would AscendToAHigherPlaneOfExistence. However, there might be hope because Shion promises that he'll meet Nezumi again at the end of the anime and novels]].
* ''Anime/NowAndThenHereAndThere'': According to most anime conventions, Shu should [[HappilyEverAfter deserve to live happily with Lala Ru after all the suffering both have been through together.]] Nope. Lala Ru dies, and any chances of Shu getting together with her Earth {{Expy}} Sarah are [[ShipSinking effectively dashed]] when he returns to his world without her. However, the audience knows from watching [[HotBlooded his character]] [[{{Determinator}} throughout the story that]] [[EarnYourHappyEnding he'll be able to live happily anyway.]]
* Played with ''Manga/OnaniMasterKurosawa''. [[spoiler: Kurosawa starts an unholy alliance with Kitahara, who later starts blackmailing him. It's the perfect set-up for an eventual love story, right? Guess again; Neither Kitahara nor Kurosawa seem particularly interested in each other, aside from their common goals. In fact, Kurosawa is in love with cute, bookish Takagawa during most of the manga. At first she seems to have an interest in him, but eventually she starts dating Nagaoka, afro-otaku extraordinaire. That can't last, right? She's the princess of the High School and he's a clown. Wrong. Kurosawa [[ADateWithRosiePalms gets over]] Takagawa, who seems quite happy with Nagaoka, and ends up dating Sugawa, the yankee that beat his ass because [[ItMakesSenseInContext he came over her uniform to avenge Kitahara]].]]
* A running gag for Sanji in ''Manga/OnePiece''. For a womanizer, no single woman is ever seen falling for him.
** Sanji does eventually get a requited love in Charlotte Pudding, but circumstances and conflicting loyalties drive them apart.
** Zoro and deceased friend Kuina are a possible example. Life was unkind to the guy.
* ''Anime/{{Patlabor}}'': No matter the continuity, Gotoh never ends up with his fellow captain, Shinobu. Throughout the OVA continuity, she maintains [[StrictlyProfessionalRelationship a strictly working-class relationship]] between them. In the end, not only does he ''not'' get the girl, [[spoiler: he finds out she once [[TeacherStudentRomance had an affair with her instructor]], while she was a cadet at the Tsuge Institute. Worse, the second Movie concludes with her turning herself in with Tsuge, [[MayDecemberRomance because she still had feelings for him]]]]. Gotoh doesn't end up with her in ''The Mobile Police/New Files'' continuity either, but they at least [[ThrowTheDogABone soften the blow a bit]] with the [[Franchise/UltraSeries Ingram-Man]] [[AffectionateParody episode]], which ends with Shinobu [[RelationshipUpgrade confessing her feelings for him.]] Except it was AllJustADream.
* In ''Manga/PokemonAdventures'', Steven teases Wallace, knowing that the real reason that the Water-type trainer stepped down from being the Champion to become a Gym Leader was for an excuse to spend more time with Winona. Too bad that is one of the reasons that is implied why they broke up. (The main reason was that Winona felt uncomfortable having someone stronger than her for a boyfriend.)
* Meowth in the ''Anime/PokemonTheOriginalSeries'' episode "Go West, Young Meowth", who tries to help his love interest who spurned him in the past. He defeats his long-hated rival Persian but the girl Meowth chooses the Persian over him anyway.
* In ''Anime/PrincessTutu'', Ahiru does not get together with Mytho, but [[spoiler: gets to stay with Fakir as a duck]].
* ''Anime/PuellaMagiMadokaMagica'': Sayaka ends up losing Kyousuke to [[spoiler:Hitomi]]. [[spoiler: This does not end well.]] Later, [[spoiler: Homura does not get Madoka. [[Anime/PuellaMagiMadokaMagicaTheMovieRebellion This does not end well either]]]].
* The anime version of ''Anime/RevolutionaryGirlUtena'': [[TheCasanova Touga]] tries to win over [[PluckyGirl Utena]] because [[ILoveYouBecauseICantControlYou she's the only girl at their school who doesn't immediately fall for him]] - in fact, she rebuffs him many times, and they ultimately don't end up together, [[spoiler:with Utena being lost in another dimension and all]]. There's also the movie, ''Adolescence of Utena'', where [[spoiler:Touga is ''[[DeadAllAlong already dead]]'']] from the beginning.
* ''Manga/SchoolRumble''. Tenma is the lead female. Kenji is the lead male. Tenma never returns Kenji's feelings; she doesn't even know about them. Not that it would really make a difference since she's too much in love with the second male lead. [[spoiler:Tenma ends up with the amnesiac, brain-damaged Karasuma. It's strongly suggested Harima ended up with Eri. The one who did not get the girl actually didn't get the guy: Yakumo. She's the only main character who definitely didn't get anyone.]]
* In the ''LightNovel/{{Slayers}}'' {{Light Novel|s}} series, the bounty hunter [[HotBlooded Luke]] constantly tries to win the affections of his [[DeadpanSnarker perpetually grumpy]] partner Millina, all to no avail. This ultimately comes to a climax in the fourteenth novel when [[spoiler:Millina is stabbed with a poisoned knife and denied any medical care]]. She more or less tells him off, telling him to keep on living and don't bother worrying about her.
* In ''Anime/TengenToppaGurrenLagann'':
** [[spoiler:Kamina dies shortly after he and Yoko admit their feelings towards each other]].
** Kittan [[spoiler:goes into a suicide mission after kissing Yoko (which cemented her status as the person with "the kiss of death" in the fandom) and it seems she reciprocated his feelings, as in her personal LotusEaterMachine one of her alternate/happier lives has her marrying him]].
** Simon and Nia [[spoiler:get married, but immediately afterward, she fades away due to an earlier HeroicSacrifice]].
* ''Anime/TheVisionOfEscaflowne'':
** The heroine, Hitomi, chooses to go back to Earth while Van stays behind in Gaia to help his world heal from the war it just endured. Despite the show being [[ExecutiveMeddling dramatically cut down]] from its planned run, that was the intended ending all along. That said, she does still have to ability to teleport instantly to his realm.
** No member of the show's LoveDodecahedron ends up with his/her {{love interest|s}} - Merle resigns to being an UnluckyChildhoodFriend, [[BelligerentSexualTension Millerna and Dryden's]] ArrangedMarriage is called off (although he still hopes to be worthy of her someday ), and Allen, who already lost the girl in the past to an ArrangedMarriage and death, loses Hitomi to Van (but does find his sister, which is probably what he wanted more than romance at that point).
* ''Anime/WelcomeToTheNHK'': though they [[BetterAsFriends stay friends]]. At least in most versions. The anime and novel both end fairly ambiguously, but the manga [[spoiler:has Satou promise to rekindle their relationship after he cleans up.]]
* The manga ending for ''Manga/XxxHolic'' follows much in the same vein. [[spoiler: Set in a DistantFinale 100 years in the future where Watanuki has lost both Himawari ''and'' [[GayOption Doumeki]] to them dying of old age. Made even sadder by the fact that after ''Tsubasa'' ended Watanuki couldn't leave his InnBetweenTheWorlds and that its very nature was harmful to Himawari making her only able to see him once a year, and she eventually moved on with her life. He comes to accept it though, congratulating her on her marriage.]]
* Hazuki from ''VisualNovel/YamiToBoushiToHonNoTabibito'' never gets her girl Hatsumi, at least in the anime, despite her valiant efforts of chasing her through several alternate dimensions. It is heavily implied that Hatsumi grants Hazuki one night with her but then erases her memory afterward, which caused quite a bit of outrage among {{yuri fan}}s.
* ''Manga/YourLieInApril'' ends with Kousei and Kaori not ending up together. [[spoiler:Kaori ''did'' love him but he didn't learn this until he read her [[DeadManWriting posthumous letter]].]]
* Played with in ''Anime/YuriOnIce'': Yuko seems this way when Yuri first meets her again, after going back to his hometown in Kyushu. He reminisces on their time growing up and learning to skate together, and comments "she's still cute," only for the viewer to learn, moments later, that she's now married with triplets ...to a guy who used to bully Yuri, no less. But of course, Yuri's [[spoiler:not exactly straight]], and we haven't met a certain manic pixie Russian figure skater just yet...

[[folder:Comic Books]]
* ''ComicBook/{{Crimson}}'': Alex Elder. First, his girlfriend is murdered by the vampire gang that turned him and her death continues to haunt him for many issues. Then, he meets [[BettyAndVeronica two other girls that fall in love with him separately, and, to some extent, he returns their feelings]]. When it appears he's finally made up his mind, the girl he chooses performs a [[HeroicSacrifice heroic sacrifice]] to save him, and the other one joins a convent, leaving him alone at the end (although it's implied he plans on reuniting with the other girl in the epilogue).
* In ''ComicBook/DramaRainaTelgemeier'', Callie is attracted to twin brothers Justin and Jesse but ends up with neither of them because Justin [[SorryImGay turns out to be gay]] and Jesse [[spoiler:''also'' turns out to be gay]]. There's a third boy who expresses interest in Callie, but she turns him down and is still single at book's end.
* ''ComicBook/TheEaglesOfRome'': Marcus survives the Battle of Teutoburg Forest and his romantic rival Lepidus is taken out, but Priscilla is raped and decapitated while his son Titus is enslaved by the Germans.
* ''ComicBook/EmpireState'': Jimmy screws up the courage to confess his feelings for Sara, only to discover that she's found a boyfriend since she moved away. She does let Jimmy kiss her, which is implied to be more out of pity than romantic attraction ("Listen, kiddo, that's just to get you through the next year or two."); if you tilt your head and squint, you could interpret it as a MaybeEverAfter ending.
* ''ComicBook/{{Family}}'': Kurt begins a relationship with Talia, but he refuses to save her criminal father Gio when he suffers a heart attack. It's implied they break up over this.
* Dave Lizewski in ''ComicBook/KickAss'' has an encounter with this trope. [[spoiler:After months of pretending to be her gay best friend, Dave [[AnguishedDeclarationOfLove finally bares his soul]] to Katie Deuxma. [[WrongGenreSavvy Expecting her to reciprocate his feelings]], Katie instead gets her boyfriend Carl to beat the crap out of him and later sends him a pornographic picture of herself with said boyfriend, [[ADateWithRosiePalms which Dave later uses.]]]]
* ''ComicBook/KingCity'': Joe and Anna broke up a couple years before the comic starts, and Anna has a new boyfriend. Joe, back in the city after being gone for those couple years, spends a fair amount of time moping over her, leading the reader to believe he'll try to win her back. But in the end, [[spoiler:after helping Anna rescue Max, Joe accepts that she's not his girl anymore. It looks like they'll remain friends]].
* Played with in a very gruesome way in ''ComicBook/LesLegendaires'' during the Anathos Cycle. As the protagonists prepare to fight the GodOfEvil Anathos, [[TheHero Danael]], feeling tired with everything that happened so far, eventually fully confess his feeling to [[MagicalGirl Jadina]] once and for all, and proposes to her after the fight. She agrees and they share a kiss... [[spoiler:then after the fight, Anathos ends up [[DemonicPossession taking over Danael's body]]. When the heroes finally defeat Anathos at the end of the Cycle, Jadina is forced to stab Danael in order to succeed. Though he's then resurrected, he has left the group and is convinced to leave the past behind him, while Jadina replaces him as TheHero.]]
* ''ComicBook/{{Raptors}}'': Benito Spiaggi is really in love with his partner Vicky Lenore to the point he is willing to do really crazy things like striking a deal with the villains to spare her life, and he is ready to die if it means she will be safe. Both of them survive by the end of the comic, but they don't get together since Vicky wanders the night hunting vampires as a new Raptor. [[SupportingProtagonist Aznar]] is also hit with this trope, since not only he kills his girlfriend by accident during sex when his vampire side awakens and he drains her dry, but he has a brief fling with Vicky yet doesn't end the story with her too since they part ways.
* ''ComicBook/TheSmurfs'': In ''The Olympic Smurfs'', for all the troubles Weakling Smurf went through, he winds up not getting Smurfette (or at least, not getting a kiss from Smurfette) by the story's end.
* As a young man, Characters/{{Superman|TheCharacter}} never married his college love [[OurMermaidsAreDifferent Lori Lemaris]], who turned down his proposal and finally married someone else. Of course, Supes eventually fell in love with [[Characters/SupermanLoisLane Lois Lane]] and even managed to stay friends with Lori, so it all worked out okay.
* In the ''[[Creator/CarlBarks Uncle Scrooge]]'' comics, one of the most attractive things for shippers about Scrooge and Goldie is that they only spent that one month together and then, driven apart by their {{pride}}, went their separate ways, never to see each other again for fifty-some years. Creator/DonRosa was strongly tempted to write more meetings between them when he took over the Scrooge [=McDuck=] Universe but resisted the temptation to ruin the tragic romanticism of this trope.
* Yorick in ''ComicBook/YTheLastMan'', in two different ways. [[spoiler: First, he discovers that his girlfriend Beth, who he has been right around the world to find again, was planning to break up with him (and even the death of all other men doesn't help). But he realized that he'd fallen in love with his bodyguard, Agent 355, and the feeling is mutual...until she's shot by a sniper. Regardless, Beth ends up with [[GirlsLove Yorrick's sister, Hero]]. So, you might say that Hero gets the girl, even if "the hero" doesn't.]]
** Yorick himself winds up marrying a minor {{love interest|s}} (who became pregnant with his child early on), and in the DistantFinale, the daughter explains that they had a troubled relationship because Yorick never stopped carrying a torch for [[spoiler: Agent 355]]. In this time period, however, the popular belief is that Yorick and Beth found each other, and true love conquered all. Yorick's daughter mocks the embellishment.

[[folder:Fan Works]]
* Spike in ''Fanfic/BeneathYourFeetWhatTreasures''; the story is about him dealing with his feelings towards Rarity via his treasure hoard, along with his knowledge that he will never get the girl.
* L in ''Fanfic/ACharmedLife''. Though he has captured Misa at the end of the story and confined her to his bondage dungeon he would have much rather have had [[HoYay Light.]]
* ''Fanfic/ADiplomaticVisit'': As seen in chapter 11 of the third story, ''Diplomacy Through Schooling''. [[spoiler: After all that ship tease between Moondancer and Twilight, and just as Twilight has decided to talk to Moondancer about taking a step forward in their relationship, Moondancer admits to Twilight that she's fallen for Trixie. The next story subverts it though when the trio talk things over, and decide to be a romantic trio.]]
* In ''{{Fanfic/Featherfall}}'' Rainbow and Gilda have a WhatCouldHaveBeen argument that ends with Rainbow revealing her feelings for Gilda in the worst way possible: [[ForcefulKiss forcefully kissing]] her when she knows Gilda is with Sunset.
* Deconstructed in ''[[https://archiveofourown.org/works/19782238 Girls Like Us]]''. Barry repeats Oliver's comment about how "Guys like us don't get the girl" to Laurel. This is her RageBreakingPoint, and she spells out for him (and Oliver) that it isn't the vigilante lifestyle that will lead to them being alone, but the fact that they don't trust or respect "the girl". Oliver and Barry are both left shaken by it.
* In ''Fanfic/{{The Masks We Wear|AvatarTheLastAirbender}}'', Zuko loses his affection for Mai as a result of his increasing similarity to his sister.
* In ''Fanfic/NewHopeUniversityMajorInMurder'', Saya Wild, the Ultimate Chess Grandmaster and the protagonist, appears to have feelings for Lucina Sorenson, the Ultimate Conductor. After the third trial, Saya rejects a kiss from Lucina, and shortly thereafter, finds out that Lucina has hooked up with Katy Thorson, the Ultimate Lesbian Romance Author. [[spoiler:In the fifth trial, in which Lucina and Katy are the primary suspects, Saya deduces that Lucina is the culprit, resulting in Lucina's execution.]] [[WhatCouldHaveBeen In an alternative outcome]] [[spoiler:to the fifth trial, Saya would have led the others to convict Katy instead. According to the author, Lucina would have become angry with the other survivors, only keeping in touch with Rocky after the killing games, but might have reconciled with the others later]]. Either way, Saya never had a chance of getting together with Lucina.
* In ''Fanfic/TheRWBYLoops'', Sun Wukong joins the looping crew only to find that Blake Belladonna, the girl he was crushing on, has been dating Yang Xiao Long for quite some time and the two are, in fact, recently engaged. Unusually for this trope, everyone is aware of the situation and somewhat sympathetic, attempting to help him move on.
* In ''Fanfic/{{Shatterheart}}'' Fai had been struggling [[spoiler: with his eventual betrayal of the group and the exhausting effects of lying to everyone]]. By the time he comes to terms with his love for Kurogane, he can't do anything about it as Kurogane has already gotten together with Syaoran and he has to watch them became lovers.
[[/folder]]

[[folder:Films -- Animated]]
* Franchise/DisneyAnimatedCanon:
** The Disney version of ''WesternAnimation/{{The Hunchback of Notre Dame|Disney}}'', which is featured as the image of this page. Unlike most of the lead males of the Disney Renaissance, Quasimodo doesn't end up with the woman he falls in love with. Namely, Esmeralda never learns of his feelings and falls for Phoebus, [[IWantMyBelovedToBeHappy though Quasimodo chooses to accept that she loves him without issue]]. He eventually gets together with another woman in the [[WesternAnimation/TheHunchbackOfNotreDameII sequel]], though.
** At the end of Disney's ''WesternAnimation/{{Pocahontas}}'', John Smith, severely injured, returns to Europe and leaves Pocahontas behind. As well as Smith being saved by Pocahontas, this is one of the only historically based moments in the entire movie and one of Disney's few {{Bittersweet Ending}}s. Exacerbated in the [[WesternAnimation/PocahontasIIJourneyToANewWorld sequel]], where Pocahontas actually ends up with a different guy, the one she married in real life.
** That [[TearJerker/TheSwordInTheStone poor squirrel lady]] from Disney's ''WesternAnimation/TheSwordInTheStone''. She falls in love with Wart while he's a squirrel, but once he turns human, she's heartbroken.
* In ''WesternAnimation/CorpseBride,'' Emily gives up her chance to marry Victor [[IWantMyBelovedToBeHappy so that he can marry Victoria instead]].
* According to Disney's ''WesternAnimation/MelodyTime'', this is actually [[JustSoStory the main reason why]] [[WolvesAlwaysHowlAtTheMoon coyotes always howl at the Moon.]]
* In ''WesternAnimation/RankinBassJackFrost,'' the titular sprite is InvisibleToNormals, but hears a beautiful girl named Elisa say that she's "in love with Jack Frost." Taking her at her word, he [[PinocchioSyndrome becomes human]], but will only stay that way if she marries him by the beginning of spring. While she and "Jack Snip" become close, he learns right before the deadline that she's fallen in love with her NewOldFlame, [[KnightInShiningArmor Sir Ravenal]]. He turns back into a sprite just as the pair are HappilyMarried.
* Shua in ''Animation/SkyBlue'' manages to bring down Ecoban, but thanks to Locke, it's almost certain Jay will die.
* ''WesternAnimation/ToyStory3'': Although Buzz Lightyear and Jessie, and to a much lesser extent, Mr. and Mrs. Potato Head and {{Franchise/Barbie}} and Ken, are now finally united with each other, Woody and Bo Peep aren't... at least until ''WesternAnimation/ToyStory4.'' (At the very beginning of the film, Bo Peep was seen only in a flashback, and when Woody lists Wheezy, RC, and the other toys that were sold before the film, Rex sheepishly adds Bo-Peep to the list; Woody is notably sad because of this.)

[[folder:Gamebooks]]
* In Douglas Hill's ''Have Your Own Extra-Terrestrial Adventure'', several of the paths have the HardboiledDetective protagonist team up with beautiful ActionGirl Mala, but in each one, they go their separate ways at the end, much to his disappointment.

[[folder:Literature]]
* Literature/AdrianMole never manages to get his most constant love interest, Pandora Braithwaite, back after the final end of their on-off (and unconsummated) relationship in their early teens. Every time he falls in love with another woman, the relationship ends disastrously, leaving him with two failed marriages behind him. However, the most recent book ends on a cliffhanger with Pandora unexpectedly arriving at his home suggesting a possibility of them finally averting this result, but the death of the author means we'll never know.
* In the ''Literature/AlbertCampion'' story ''Mystery Mile'', Campion admires Biddy Paget and is upset when [[spoiler:she chooses Marlowe Lobbett instead]].
* Most of Jeremy's actions in ''Literature/BeMoreChill'', up to and including getting a SQUIP in the first place, are intended to help him get with Christine. After the incident at the school play, they end the story on a negative note, and it's left ambiguous if Jeremy's explanation will help them reconcile.
* ''Literature/BookOfTheNewSun'': Severian's first love, Thecla ends up [[spoiler:killing herself to avoid the torture]] and his amnesiac second love, Dorcas leaves him when she finds out that [[spoiler:she is his grandmother]]. It should be noted that although [[spoiler:Thecla dies, Severian's persona is merged with hers through a sort of cannibalistic Eucharist]].
%%* Truman Capote's novel, ''Literature/BreakfastAtTiffanys''. [[Film/BreakfastAtTiffanys The film adaptation]], of course, changed this.
* Creator/CharlesDickens gives this fate to Scrooge in ''Literature/AChristmasCarol''; although he was deeply in love with Belle, his pursuit of fortune eventually drove her to break off their engagement. The Ghost of Christmas Present shows him what she's doing now - she married someone else and is the matriarch of a loving family, and Scrooge is devastated to think that he could have had this with her if he'd been less materialistic.
* ''Literature/ClockpunkAndTheVitalizer'': Clockpunk doesn't get with the Vitalizer. It's probably for the best since she's a superhero and he a supervillain. [[spoiler:He [[WorthyOpponent shows her some respect]] before fleeing, however.]]
* ''Literature/DaisyMiller'' is not a sad book because [[spoiler:the girl dies]], but because the guy doesn't realize her worth [[spoiler:while she's alive]].
* In the ''Literature/DeptfordMice'' trilogy by Creator/RobinJarvis, Piccadilly is in love with Audrey, despite wrongly believing that she hates him. In reality, she loves him just as much as he loves her. After she unintentionally insults Piccadilly and he returns to his home in the city, Audrey visits her friend Twit's field, Fennywolde. While there, she ends up falsely accused of being a witch and sentenced to hang. According to the Gallows Law, if a willing spouse can be found, then the accused will be reprieved. Twit offers to marry Audrey, and she accepts because it's the only way she can be saved. However, she regrets her decision because she cannot pursue a romantic relationship with Piccadilly. He is killed without knowing of her love for him, but she does confess her feelings to his ghost and they kiss before he crosses over to the other side.
* Kelson falls deeply in love with Rothana Nur Hallaj, a Literature/{{Deryni}} princess who is a novice at a convent called St. Brigid's (which is sacked by Ithel of Meara's forces in ''The King's Justice''). They make tentative plans to wed (she writes to Archbishop Cardiel to have her temporary vows set aside) before he leaves on his quest for Camber relics, but when he and Dhugal are thought to be dead, she is persuaded to marry Kelson's cousin Conall instead. Not only does Kelson return to find her married to Conall [[spoiler: and carrying his son]], Conall's actions leave Rothana somewhat tainted by association. Though Kelson is quite willing to marry her after Conall's execution, she refuses him and plays matchmaker for Kelson and his distant cousin Araxie Haldane.
* Creator/TerryPratchett's ''Literature/{{Discworld}}'':
** In ''Literature/{{Sourcery}}''; Rincewind meets Conina, daughter of Conan the Barbarian, and while in Al Khali searching for the Arch-Chancellor's hat, begins to develop a crush on her. Later, he meets wannabe barbarian Nijel who ends up falling for Conina and vice versa.
** ''Literature/{{Pyramids}}'' ([[spoiler:see also: Franchise/StarWars]].)
** ''Literature/InterestingTimes''
** ''Not'' ''Literature/GuardsGuards'', despite Vimes' tendency to quote ''Casablanca'' (see).
** In his non-Discworld novel ''Literature/{{Nation}}'', Mau and Daphne do not end up together due to their duties and obligations to their respective cultures, though it's implied they are reincarnated as paired dolphins after their deaths.
* Creator/JimButcher's ''Literature/TheDresdenFiles'': Harry Dresden. He's had four LoveInterests in 14 books, and it hasn't worked out with any of them. [[WordOfGod Jim Butcher has even stated that he has no idea who Harry ends up with]]. In order:
** Elaine (who shows up later in the books than Susan, but whom Harry has known longer): She and Harry fall in love when they teenagers both apprenticed to a dark wizard; when Harry turns against the dark wizard, Elaine betrays and nearly kills him (we later find out she was under a geas); and now they've run into each other occasionally but are in no kind of relationship.
** Susan Rodriguez was the steadiest girlfriend he had, and they were genuinely in love. [[spoiler:Literally; Susan's love for Harry protects him from the White Court.]] Unfortunately, [[spoiler:bad decisions on both their parts ended with Susan becoming a half-vampire and forced to go on the run for the rest of her life, though not without carrying Harry's child]]. In the end, [[spoiler:[[ADeathInTheLimelight Harry ends up killing her]] to trigger a bloodline curse that kills all of the Red Court vampires in the world]]. Ouch...
--> "[[spoiler: And I...]]\\
[[spoiler: [[ShootTheDog I used the knife.]]]]
--> [[spoiler: [[TearsOfRemorse I saved a child.]]]]
--> [[spoiler: [[DiedInYourArmsTonight I won a war.]]]]
--> [[spoiler: [[MyGodWhatHaveIDone God forgive me.]]]]"
** Shiela, a girl working at an occult bookstore with perfect memory recall, seems like a good possibility in ''Literature/DeadBeat''. [[spoiler:Turns out she's just a psychic projection/mental clone created by the FallenAngel residing in Harry's head.]] He does actually manage to [[spoiler:redeem the demonic entity, right before she kills herself to save his life]]. Although WordOfGod is that [[spoiler: Lash showed up in ''Literature/GhostStory''... somewhere, as did Lasciel]].
--> "''[[spoiler: [[TearJerker Anything I can my host.]]]]''"
** Anastasia Luccio, fellow wizard [[ReallySevenHundredYearsOld born three centuries ago]], who got dumped in a pretty young girl's body via magic and developed a budding relationship with Harry. [[spoiler:Turns out she was mind-controlled by an agent of the Black Council into being attracted to Harry to keep tabs on him.]] That...really puts a downer on that romance.
** Karrin Murphy, who Harry has the most ongoing chemistry with. They planned to take the "unresolved" out of their UnresolvedSexualTension at the end of ''Literature/{{Changes}}'', but then [[spoiler:Harry catches a bad case of sniper]]. In ''Literature/ColdDays'', Karrin and Harry finally have TheBigDamnKiss, but she has very good reasons to hesitate, such as [[spoiler:Harry gets a hard-on during the Big Damn Battle, thanks to the Winter Knight's Mantle]] and a potential match for Harry in Molly who is now [[spoiler:the Winter Lady after Maeve's death]]. Karen's own emotional baggage, and personal issues, also play a big part in her decision.
--> You may be the master of disaster, but I've been the one to steer relationships into icebergs.
** Harry ''does'' [[spoiler: agree with her that they both need more time to get their heads together, but that once they do, "we set sail for the fucking iceberg, full speed ahead" Karren agrees. At the end of ''Skin Game'', they eventually decide to just go for it after realizing that the "right time" will never come and they might as well take the opportunity while they have it, possibly averting this trope]].
** Harry ''did'' manage to bed [[spoiler:Mab, the Winter Queen of Faerie, Queen of Air and Darkness]]. But ''nothing'' good is coming out of ''that''.
* Creator/ETAHoffmann:
** In ''Literature/TheArtushof'' Traugott makes this a habit. He does not get Christina (the girl he was engaged to) because he wants Felizitas. He quests for her after her father kicks him out of the house, and manages to attract Dorina, the daughter of another painter he stays with, but when he won't marry her, he gets kicked out. When he gets home after not getting two girls he finds out Felizitas got married to another man. Three strikes and you're out.
** In ''Literature/TheEntail'' Theodore devotes all his time in Castle R into trying to get with Baroness Seraphine but when he ends up having to leave when he returns, he hears she died in a sleigh crash.
** In ''Literature/TheSandman1816'' Nathaniel doesn't end up with his childhood sweetheart Clara nor the other girl who he fell for that happened to be a robot. Oops.
* Robin Hobb’s ''[[Literature/RealmOfTheElderlings Farseer Trilogy]]'' is possibly one of the most depressing examples. [[spoiler:Remedied at the end of the ''Tawny Man'' trilogy, in which FitzChivalry ''finally does'' get the girl he had wanted to be with the entire time after her husband dies, something like thirty or forty years later. A clear case of EarnYourHappyEnding]].
* Both of the books in Marti Steussy's "First-In" duology have {{bittersweet|Ending}} gender-flipped examples. In ''Forest of the Night'', [[spoiler:Gaylord Hess]] spurs the conflict between humanity and the [[IntelligentGerbil Lodgeless Ones]]; by the time he gets a clue, his agitation has caused several deaths on each side and it's clear that he's never going to fully appreciate or understand Hashti's position. In ''Dreams of Dawn'', [[spoiler:Aage]] is simply too reluctant to compromise on the dilemma regarding the world's MirrorChemistry, leading Disa to ultimately distance herself from him. ''Forest'' leaves [[spoiler:Gaylord's and Hashti's]] romantic futures ambiguous[[spoiler:; the DistantFinale of ''Dreams'' gives both Disa and Aage {{Second Love}}s: another young First-In member for Disa, and the [[GirlNextDoor sweet local girl Gretchen]] for Aaage]].
* ''Literature/TheFirstLaw'':
** Played straight with Logen/Ferro and Jezal/Ardee, making ''two'' heroes who did not get the girl...but, at Jezal's expense, deliciously subverts it with Glokta, Hero #3... depending, of course, on how you define "hero". He and Ardee marry, in no small part to save her from the consequences of Jezal's bad judgement, and end up in a stable, affectionate relationship.
** Gorst in one of the sequels, whose love interest doesn't even notice his AnguishedDeclarationOfLove, and is HappilyMarried anyway.
* Actually lampshaded at the end of the ''Forgotten Realms'' novel, Escape From Undermountain as the protagonist Artek expresses his disbelief over not getting the girl and her declaring 'not in this story'.
* Martin Cruz Smith's ''Literature/GorkyPark''. [[spoiler:Arkady Renko]] tells [[BreakTheCutie damaged love interest]] [[spoiler:Irina Asanova]] to stay [[spoiler:in America]] while [[spoiler:he'll return to]] UsefulNotes/ColdWar era Russia. [[spoiler:It was her dream to escape the Soviet Union, and Renko doesn't find America to be any better than the USSR.]]
%%* The original ending of ''Literature/GreatExpectations''.
* Despite all of the eponymous character's attempts to win the girl in ''Literature/TheGreatGatsby'', she stays with her husband. Gatsby takes a lie for her that gets him killed.
* Severus Snape [[spoiler: did not get the girl, the girl being Lily Potter nee Evans,]] before the events of the ''Literature/HarryPotter'' series, as revealed in ''Literature/HarryPotterAndTheDeathlyHallows''.
* ''Literature/HisDarkMaterials'': Will and Lyra. While they do share a mutual attraction to each other and eventually spend some romantic time together, it can't last since the laws of the multiverse decree that they live in their separate universes and try to make the world a better place individually. Whether this is a lame ending or a TearJerker depends on the reader.
* ''Literature/HollowPlaces'' features a variation of this trope. Austin does end up with Isabella, but by then she's so different from the woman he fell in love with, she could hardly be called the same person.
%%* ''Literature/TheHunchbackOfNotreDame''. Probably the TropeCodifier.
%%-->'''Quasimodo:''' ''(To a statue, sobbing)'' Why was I not made of stone like thee?
* Eragon from the ''Literature/InheritanceCycle''. Never mind that [[spoiler: Arya got a dragon, and her dragon and Saphira ''immediately'' shacked up, so both she and Eragon had a mental link to sex... except Eragon has spent a long time learning to control the link, and she hasn't. The girl he's been drooling over for the better part of four books and a year or two, they're both horny beyond their control, alone, and... they sit and chat. If [[MemeticMutation Forever Alone]] has a patron saint, it's this guy]].
* Occasionally happens in the ''Literature/JackReacher'' novels. [[spoiler:''Die Trying'' is an example; while Reacher and the female lead have a mutual attraction and once engage in GladToBeAliveSex, she is in love with someone else and moves in with (and possibly marries) him at the end of the novel]].
* Happens in Creator/IanFleming's ''Literature/JamesBond'' novels more regularly than the films would have you believe. (In the very [[Literature/CasinoRoyale first novel]], the love interest [[spoiler:commits suicide]], in ''Literature/{{Moonraker}}'' she's engaged to another man, in ''Literature/OnHerMajestysSecretService'' his [[spoiler:wife is murdered at the end]], and in ''Literature/FromRussiaWithLove'' Bond is poisoned before any consummation can occur).
* Thomas Hardy's ''Literature/JudeTheObscure''. Subverted in that he does get a girl, but she's not the main romantic lead and she's a complete harpy. Played straight in that Sue decides to go back to Philloston after the big tragedy.
* ''Creator/HansChristianAndersen'''s "Literature/TheLittleMermaid" does not get her Prince, though in every way she deserves it. Here, too, [[WesternAnimation/TheLittleMermaid1989 the film adaptation]] changed this (and even added [[WesternAnimation/TheLittleMermaidIIReturnToTheSea a sequel]] about the daughter born to the marriage which did not happen in the original...) The princess in another one of his fairy tales, "[[http://hca.gilead.org.il/swineher.html The Swineherd]]", does not get the prince because she cares more about the musical toy that he created than she does about him. Unlike the little mermaid, this princess does not deserve the prince at all - she's too materialistic to love him for who he is.
* ''Literature/LittleWomen'': TheOneGuy Laurie does not get the member of the starring FourGirlEnsemble he originally wanted, who is ''also'' the one both the original and the modern fanbase [[FanPreferredCouple wanted him to get]]. It's not like there isn't a Fritz/Jo fandom or their UmbrellaOfTogetherness scene isn't the very essence of sweet and romantic. Laurie/Amy, [[DieForOurShip on the other hand]]...
* Circe and Calypso in ''Literature/TheOdyssey'' - both fall in love with Odysseus and want to keep him on their islands, but due to divine intervention (Hermes usually is involved) they have to let him go eventually. Calypso even lampshades it, complaining that goddesses are always quickly separated from their mortal lovers, usually by a god killing them.
* Freida in ''Literature/OnlyEverYours'' doesn't get her love interest Darwin, when she tries too hard to convince him to choose her as his companion (strictly forbidden under the dystopian society in which they live) and is [[spoiler:disqualified from the Ceremony, forced to become a chastity]]. He instead chooses and marries her enemy Megan.
* The ending of the classic Robert Munsch children's tale ''Literature/ThePaperBagPrincess'' has the eponymous heroine not getting the prince because she looks too unkempt. She therefore decides that the prince isn't good for her if he won't accept the way she looks, and calls him a bum. The last line of it is "They didn't get married after all." In the short animated adaption of this story, she hooks up with the dragon instead. Dead serious.
* Creator/KimStanleyRobinson's ''Pacific Edge''. Kevin Claiborne does not get Ramona; instead, she goes back to her {{Jerkass}} boyfriend, Alfredo.
* Anthony Hope's ''Literature/ThePrisonerOfZenda''. The girl is expected to marry the actual king instead of his decoy double (with whom she's fallen in love).
%%* This is what kickstarts the philosophizing in ''Franchise/{{Repetition}}''.
* ''Literature/TheReynardCycle'': ''Reynard the Fox'' ends heavily on this note, and it gets worse with every new installment.
* In ''Literature/RogueStar'', Andy Quamodian spends most of the book trying to rescue [[DamselInDistress Molly Zaldiver]] who he's [[DoggedNiceGuy always been in love with]], but in the end, the only way she can survive is to [[spoiler: [[HiveMind merge with]] the living star Almalik]].
* A ForegoneConclusion of ''Literature/SavingCharlie'', as anyone who's seen the episodes of ''Series/{{Heroes}}'' that it's based upon knows that Hiro doesn't manage to save Charlie (though [[TheyDo he does "get" the girl]], she ends up dead immediately after and has convinced him that it's in the best interest of the world not to alter the timeline just to save her).
* ''Literature/ASongOfIceAndFire'': If one goes with the theory that Petyr 'Littlefinger' Baelish is what would happen if a stereotypical fantasy hero was plonked into a CrapsackWorld, then this is the reason why he's so screwed up and [[spoiler: why Westeros is now even more of a CrapsackWorld]].
* In Creator/PoulAnderson's "Starfog", Laure does not get Graydal. The ''Jaccavrie'' AI explains it's impossible: they aren't interfertile, and her kind have developed [[MandatoryMotherhood a compulsive need to reproduce]].

* ''Literature/TailchasersSong'': Tailchaser starts the book looking for Hushpad but gets sidetracked with more dire issues along the way. He finally finds her, but they've grown apart. Hushpad is fine being an inside cat, living amongst Big Ones, and sleeping all day, while Tailchaser desires adventure and can't handle being smothered by humans. Tailchaser wants kittens but Hushpad doesn't (plus, [[spoiler:it's heavily implied she's spayed]]). Eventually this gets to be too much and Tailchaser leaves Hushpad and her owners.
* In Creator/PoulAnderson's ''Literature/TechnicHistory'' story "The Star Plunderer" the narrator was captured with his girlfriend. Through a revolt, they become involved in the founding of the Empire-- and she becomes the empress, leaving him behind.
* Creator/IsaacAsimov's "Literature/TrueLove": The surprising PlotTwist at the end has Milton end up [[spoiler:going to jail while Joe gets the girl]].
* Adam and Nina's repeated failures to get married drive much of the plot of ''Literature/VileBodies''. She eventually gives up on their engagement and marries Ginger because he has money. Nina continues to sleep with Adam occasionally afterwards and may even [[MamasBabyPapasMaybe be pregnant by him]] at the end, but is clearly not interested in leaving Ginger and appears oblivious to how Adam might feel about it. Like everything else in the novel, this situation is played for black comedy.
* ExaggeratedTrope in ''Literature/VitaNuova''; [[Creator/DanteAlighieri our hero]] can't even manage to get his crush to say hello to him, much less love him back.
* In the children's book ''Literature/TheWainscottWeasel'', the title weasel does not get his love interest ([[InterspeciesRomance a striped bass named Bridget]]) due to the humans cutting out the pond.
* ''Literature/WarriorCats'': Ashfur did not get [[ADogNamedCat Squirrelflight]], Thrushpelt did not get Bluestar, and several notable genderbent examples include Cinderpelt and Firestar, Spottedleaf and Firestar, Mapleshade and Appledusk, Feathertail and Crowfeather, and Leopardstar did not get Tigerstar.
* In ''Literature/WutheringHeights'' Heathcliff does ''not'' get Catherine. In fact, he marries her sister-in-law Isabella.
* Creator/DeanKoontz's novel ''Your Heart Belongs to Me'' ends like this, which is something of a break in formula for him.

[[folder:Live-Action TV]]
* Throughout the first season of ''Series/AgentsOfSHIELD'', there is considerable ShipTease between Ward and Skye. Then she learns that [[spoiler:he's TheMole]] and rejects him. Her second love interest, Lincoln, [[spoiler:performs a HeroicSacrifice to save the world]].
* ''Series/ANTFarm'': Chyna showed signs of this a la Ranka Lee at the near end of the episode ''[=MeANT=] To Be?'', which implied that she wished she wanted to get a chance of fully loving Fletcher. More worse considering it's the 2nd to last episode, but luckily averted in the finale where Fletcher and Olive (her friend) broke up as well as Fletcher stays in New York, but even then, Chyna still never gets a chance to love Fletcher.
* Lee "Apollo" Adama on the new ''Series/{{Battlestar Galactica|2003}}'' is practically the patron saint of this trope. He blows it with ''at least'' four women over the course of the show: [[spoiler:Kara "Starbuck" Thrace, his [[StarCrossedLovers Star-Crossed Lover]], who marries another man, dies suddenly, comes back, then disappears again leaving him standing all alone in the middle of a field and that's literally the last that's seen of him in the series. Anastasia Dualla, who he sniped away from the show's DoggedNiceGuy Billy Keikeya. She married him, divorced him, then killed herself. Gianne, his ex-fiance, who he ran out on when she was pregnant with his child no less. Shevon, a prostitute he frequents for [[BizarroEpisode all of one episode]] and ReplacementGoldfish for Gianne, who pushes him away because, well, she's a prostitute]].
%%* The ''Series/{{Blackadder}} II'' episode "Bells".
* In ''Series/TheBrittasEmpire'', Gordon Brittas ultimately loses Laura, who he had considerable sexual tension with, to her estranged husband, Michael T. Farrell III.
* ''Franchise/{{Buffyverse}}'':
** Buffy and Angel in Season 3 and then Buffy and Spike in Season 7.
** Buffy and [[PutOnABus Riley]], Willow and [[InstantDeathBullet Tara]], Xander and [[InTheBack Anya]], [[HoYay Andrew and Jonathan]], and Giles and [[NeckSnap Jenny]] for ''Series/BuffyTheVampireSlayer''.
** Along with Angel and [[DeadAllAlong Cordelia]], [[IDidWhatIHadToDo Gunn]] and Fred, Wesley and [[DemonicPossession Fred]], and [[HumanoidAbomination Illyria]] and Wesley all of ''Series/{{Angel}}''. Usually because of one of the people involved dying.
* In the BBC version of ''Series/{{Casanova}}'', the titular character [[TearJerker tragically]] did not get the girl. The Hollywood version cheapens the story with a tacked-on happy ending.
* ''Series/DawsonsCreek'' ends with [[spoiler: Joey choosing Pacey over Dawson]].
* ''Series/{{Degrassi}}'' has JT's AbhorrentAdmirer Liberty have a crush him for a long time. When they do finally get together, they end up breaking up and he died before they could get back together (shortly after revealing to his best friend he was still in love with her, and this happened on her birthday).
* ''Series/DoctorWho'':
** The Doctor occasionally does this, although mostly in the Revival. He didn't get together with Rose due to a combination of CannotSpitItOut and her getting stuck in an alternate universe. Even if he does succeed in romance, it's probably not going to last, because of his [[WhoWantsToLiveForever near-immortality]].
** They do get a somewhat happy ending at the end of Series 4. Due to a complicated series of events wherein the Doctor undergoes a partial regeneration which he aborts by channelling into his [[ChekhovsGun spare hand]], the hand later grows into a Half-Human clone of the Doctor after absorbing some of Donna's DNA. The Doctor decides to leave his doppelganger with Rose in the alternate universe, knowing that he can grow old with her and give her a life that he never could.
** Back in the Classic Who days, Sarah Jane was something of an ImpliedLoveInterest for the Fourth Doctor. Despite plenty of {{U|nresolvedSexualTension}}ST, nothing happened whatsoever and he eventually abandoned her several hundred miles away from where she was actually from and [[ForgottenFallenFriend never spoke about her again]]. In a Tenth Doctor episode, the Doctor finally confirms that his Fourth incarnation had been in love with her, but he'd chosen not to pursue his feelings because of the MayflyDecemberRomance factor and because he's bad at handling goodbyes. He then [[ReincarnationRomance finally tells her with his new face]], "[[LoveConfession I Love You, Sarah Jane]]", before leaving her again. Even more of a TearJerker after the RealLife passing of Creator/ElisabethSladen from cancer in 2011.
** ''Flux'' starts with Dan and Diane's budding romance which gets sidelined by the series' big StoryArc. In the end, she rejects his offer for another date after all she's been through.
* [[FaceDeathWithDignity November]] and Paul, [[IWantMyBelovedToBeHappy Alpha]] and Echo, [[SurvivorGuilt Topher]] and [[OneHitKill Bennett]], and [[EsotericHappyEnding Echo and Paul]], all from ''{{Series/Dollhouse}}''.
* ''Series/ICarly'': Carly Shay doesn't get the guy at the end of "[=iOMG=]", a season finale cliffhanger. By the end of the real finale, [[spoiler:Sam doesn't end up with Freddie either, but Carly ''does'' get the guy right before she leaves]].
* Played for laughs with Simon Cooper in ''Series/TheInbetweeners''. He spends the course of the entire show trying to win her over, usually blowing it in hilarious ways. He does get to kiss her in the final episode of series 2, but she goes back to her boyfriend.
* ''Series/KamenRiderDouble'' hinted in early episodes that Shotaro would eventually get together with Akiko, only for her to end up with [[JerkWithAHeartOfGold Terui]] instead.
* ''Series/MaddigansQuest'' made it clear from the beginning that this would be how the UnresolvedSexualTension between Garland and Timon, since whether they won or lost, Timon would have to return to the future.
* Lancelot from ''Series/{{Merlin 2008}}''. In this version, Arthur/Guinevere is not a political marriage, but a real love connection. Also Merlin and Freya. [[spoiler:Guinevere doesn't get the guy, with Arthur dying at the end.]]
* In the Japanese drama ''Naka nai to Kimeta Hi'', the protagonist loses her love interest when a rival successfully seduces him and ends up marrying him. It is then suggested that she may end up with a senior at work who has sympathy for her and supports her in her career - but that doesn't happen either.
* ''Series/NightCourt'' - though Harry and Christine gave it an honest shot.
* Brian Kinney at the end of the US version of ''Series/QueerAsFolk''. Despite having declared his love for Justin and even proposing marriage, which was what Justin wanted even though it went against everything playboy Brian believed in, [[spoiler: the couple split up so that Justin could pursue an art career in NYC]]. {{Word of God}} says this was not a breakup.
* Allan-a-Dale from ''Series/RobinHood'' was given two possible love interests and lost them both to other characters. [[spoiler:[[ShootTheShaggyDog And then they killed him off]].]]
* ''Series/SchittsCreek'': In Season 6, Ted is offered a permanent position in the Galapagos Islands and Alexis's PR career starts to take off, eventually prompting a move to New York. After a heartfelt and heartbreaking talk, they realize that, despite loving each other deeply, their lives are taking them in different directions and they break up.
* Happens several times in ''Series/{{Skins}}'':
** Tony and Michelle end up going their separate ways because of different universities.
** Generation 1 ends inconclusively whether Sid reunited with Cassie in the US. "Skins Pure" reveals that they did not get together again.
** Franky ultimately rejects both Levan brothers, which isn't so bad given how unlikable she became in the sixth series.
* ''Series/{{Smallville}}'' - [[ForegoneConclusion It should be extremely obvious]] to anyone with even a passing knowledge of ComicBook/{{Superman}} lore that Clark and Lana do not end up together.
* ''Franchise/SuperSentai'' has a few examples:
** ''Series/HikariSentaiMaskman'': Takeru does not end up with Iyal because she is now the queen of Tube and is forbidden to have a relationship with a human. The hint being Iyal saying to Takeru to "Never look back" was a sign that she meant "Forget about me, you still have your friends waiting for you."
** ''Series/MiraiSentaiTimeranger'': Tatsuya and Yuuri cannot be together because she has to go back to the year 3000. Domon has to go too, meaning that he cannot be with Honami - this is played for TearJerker effect when he returns for ''Series/KaizokuSentaiGokaiger''.
** ''Series/EngineSentaiGoOnger'' showed that Sosuke and Miu had feelings for each other, but ultimately nothing comes of it and they return to their respective lives.
** [[Series/JukenSentaiGekiranger GekiRed]], [[Series/NinpuuSentaiHurricaneger HurricaneRed]] and [[Series/TensouSentaiGoseiger GoseiRed]] all have movie-only love interests that don't re-appear for the TV series, thus they do not get the girl.
** ''Series/ZyudenSentaiKyoryuger'': Yayoi was shown to have a huge crush on Daigo from her introduction, and was determined to win him over. Despite the mild ShipTease between Yayoi and Daigo that followed, including weathering the visit of pop star Mikoto, who Daigo was shown to be very close to and protective of, it was Amy who ended up with Daigo, a romance that was suddenly dropped on viewers' heads during ''[[LastMinuteHookup the last three episodes]]''. Yayoi, who declared early on that she would not lose to Amy, seemed to just suddenly quit pursuing Daigo and was [[IWantMyBelovedToBeHappy apparently okay with letting Daigo and Amy be together]].
%%* Several from the Franchise/UltraSeries:
%%** Dan from ''Series/UltraSeven''
%%** Komon from ''Series/UltramanNexus''
* Early on in ''Series/{{Victorious}}'', the show seemed to be setting up a relationship between Tori and Beck. When Beck broke up with his girlfriend, Jade, there were several [[ShipTease Ship Teasing]] moments between him and Tori. However, he eventually gets back together with Jade by the end of the series. It should be noted that the show ended unexpectedly, and many plot lines were ended prematurely.
* Jack in ''Series/WildBoys''. Despite sharing a smoldering look in the finale, Mary ends up staying with Mick, and Jack rides off with Dan.
* ''Series/TheWonderYears'' ends with a closing epilogue revealing that, after six seasons, [[spoiler: Kevin and Winnie part ways and he ends up marrying someone else]].

[[folder:Music]]
* Music/AmonAmarth's ConceptAlbum ''Jomsviking'' has the male protagonist kill an earl's servant to protect his love from DroitDuSeigneur and have to flee town. He ends up a warrior with the Jomsvikings and, in the song "A Dream that Cannot Be", returns to get his OldFlame (whose part is sung by Music/{{Doro}}) and bring her into his new life. She tells him to piss off and then pulls a knife on him when he tries to force the issue.
* "7 & 7," by the Music/TurnpikeTroubadours, has the narrator pondering a failed relationship, and wondering what might have happened if he hadn't been [[HeelRealization "the boy who your mama warned you about."]]
-->''That old scene is always coming to me''\\
''I see you standing with your husband and your child''\\
''And you're a picture of strength and grace and beauty''\\
''And me, I'm just a fool in a supermarket aisle''\\
''Well I know "hello" would surely end up awkward''\\
''I never had the knack for talking anyway''\\
''And you're not the kind for bending over backward''\\
''So I smiled and turned my shopping cart around and walked away''
* Rhett Akin's "That Ain't My Truck," about a guy in a LoveTriangle who gives his lover an ultimatum to choose. He doesn't hear from her, so he swings by her house, and finds:
-->''That ain't my truck in her drive\\
Man, this ain't my day tonight\\
Looks like she's in love and I'm out of luck\\
That ain't my shadow on her wall\\
Lord, this don't look good at all\\
That's my girl\\
My whole world\\
But that ain't my truck''

[[folder:Theater]]
* Creator/GeorgeBernardShaw's play ''Theatre/{{Pygmalion}}'', but not the musical ''Theatre/MyFairLady'' or for that matter most other PygmalionPlot adaptations.
* ''Theatre/SweetCharity''. Although all signs point to the contrary, Oscar winds up leaving Charity.
%%* Jack Point in Creator/GilbertAndSullivan's ''Theatre/TheYeomenOfTheGuard'' plays it straight.
* On a more comical note, ''Theatre/{{Patience}}'' is subtitled ''Bunthorne's Bride''. Guess who is the only male character in the play to end up without a bride...
* ''The Student Prince'': In a huge TearJerker moment, just as the titular prince is about to defy his father and marry the commoner he's fallen in love with... he learns his father is dying. He agrees to marry for diplomatic reasons, and takes up the crown, but goes to see his true love once more before he does.
* A Did Not Get The Guy example: Kathy in ''Vanities''. She apparently [[TheMourningAfter never finds another.]]
* ''Theatre/CyranoDeBergerac'': [[LoveDodecahedron Cyrano, Christian and De Guiche love Roxane]]. No one of them will get her. Roxane won’t get any guy too, because she's been LovingAShadow. Even Raguenau is abandoned by his wife, Lisa. Nobody gets anyone.
* Creator/PeterUstinov's play ''The Love of the Four Colonels'' is set in Germany shortly after World War 2, where the four titular officers -- one from each occupying power -- come across Sleeping Beauty's castle and fall in love with her. Due to the machinations of the good and evil fairy, none of them gets the princess -- the British and the Soviet colonel return to their wives (even though e. g. the Russian one has in the meantime given birth to another man's child), while the American and the Frenchman have themselves put to sleep so that in another 100 years they'll have another go at wooing her, even though they just know that the fairies will ensure that neither of them is successful.
* Jonathan Larson's semi-autobiographical play, ''Theatre/TickTickBoom'', has the protagonist choose between pursuing his dream of being a famous composer and settling down with his girlfriend Susan and a steady job. The stakes rise when Susan tells him she is moving away and wants him to come with her. In the end, he chooses to stay and pursue his dream, and they decide to be JustFriends, and for his birthday she gives him sheets of blank paper with which to write to her.
* In ''Theatre/StreetScene'', Sam is crushed when Rose leaves him in the end, having decided that, after what happened with her parents, she can't let their lives be tied together.
* In ''Theatre/ThePlayboyOfTheWesternWorld'', Pegeen Mike rejects Christy Mahon in the end. It's not a downer ending for him, though; he gets so much else that he's got a good chance of getting over the rejection -- whereas she regrets her decision deeply as soon as it's too late to take it back.
* ''Theatre/TheMisanthrope'': Alceste refuses Célimène's offer of marriage because he's finally sure that she doesn't love him (or at least doesn't love him any more than she loves any man who pays attention to her).

[[folder:Video Games]]
* ''VideoGame/{{Alundra}}'': The title character's DistaffCounterpart, who is subtly teased as being a potential love interest from the moment she appears at the game's midpoint, [[WalkingTheEarth walks the earth]] with him for a while in the ending, and then leaves him to his own devices. Cock tease. At least she gave him a kiss before parting ways, maybe to soften the blow that regardless if they separate, they're still going to be friends and maybe their paths will cross again. [[AndTheAdventureContinues Who knows.]] [[HeroicMime Alundra's face showed no disappointment anyway.]]
* In ''VideoGame/BahamutLagoon'', Byuu does ''not'' end up with [[spoiler: [[UnluckyChildhoodFriend Princess Yoyo]]. She ends up [[StockholmSyndrome falling for Palpaleos]], the enemy general who keeps her kidnapped]].
* A possible outcome in the ending of ''VideoGame/{{Catherine}}''. [[spoiler:It leads to a satisfying ending for Vincent because it presents a personal liberation for him, and he can either win a huge amount of money and start a new life elsewhere or at least have a good laugh at the expense of Boss.]]
* Played with in the BittersweetEnding of ''VideoGame/DeadlyPremonition''. [[spoiler: York does, but Zach (the player character) does not.]]
* ''VideoGame/DiscworldNoir'': [[spoiler: Lewton doesn't get either of his love interests. Ilsa leaves Ankh-Morpork with her husband, and Lewton has [[FemmeFatale Carlotta]] arrested by the City Watch for her involvement in the murders]].
* In ''VideoGame/Disgaea5'', Seraphina is set up as the game's heroine who shows obvious signs of falling for Killia due to him being immune to her overload. Towards the end of the game [[spoiler:Killia finds out he can possibly save his lost love from before the game started, Liezerota]], and Seraphina stops acting {{tsundere}} and comes to the sad realization that there is no room in Killia's heart for her beyond friends. She tries one last time to use her skill on Killia (with his permission), and when it fails she somberly admits his love for [[spoiler:Lieze]] is too strong and she never stood a chance. She also replaces all of the pictures of herself in her lounge with pictures of Killia.
* ''Franchise/DragonAge'':
** ''VideoGame/DragonAgeOrigins'':
*** Most of the origin stories include an extra one-sided-or-not {{love interest|s}}, and in fact, every female Warden can run into one in hers. Needless to say, she won't get to keep him even if she wants to, a fact which is sometimes presented [[TearJerker rather painfully]].
*** Any male Warden who romanced Morrigan has this occur prior to end-game. The entire plot of "Witch Hunt" has the Warden attempting to track down Morrigan [[spoiler: and their child]].
** ''VideoGame/DragonAgeII'' reveals this to be the fate of a Warden who romanced Leliana or Zevran, as the Warden seems to have vanished. [[spoiler:It's revealed the Warden embarked on a quest to save their order from their premature destruction and that happens in literally every other romance option... Except for Zevran who is accompanying the Warden]].
** ''VideoGame/DragonAgeII'' has this occur repeatedly. Notable examples are if Hawke slept with Isabela but later romanced another character, several lines of dialogue hint that Isabela still has lingering feelings and regret over the relationship ending. It's also implied that Anders falls in love with Hawke even if Hawke doesn't romance him (dialogue he has in a playthrough where he ''is'' romanced basically confirms this). If a female Hawke romances Sebastian, but sides with the Mages and refuses to kill [[spoiler: Anders]], he breaks up with Hawke and leaves to raise an army to wage war on Kirkwall.
** ''VideoGame/DragonAgeInquisition'': This can happen to certain love interests under specific circumstances: if they romance Cassandra, their relationship can potentially end if [[spoiler:she is chosen as the Divine]]; with Cullen if he is [[spoiler:encouraged to take lyrium, ending with him becoming an AddledAddict]]; with Iron Bull if [[spoiler:he upholds the Qun which will result in him betraying the team in the ''Trespasser'' DLC]]; with Blackwall if [[spoiler:he is not rescued from prison after TheReveal of his true identity]]; or with Sera if [[spoiler:your character is an elf and refuses to abandon her religious beliefs]]. The one instance that will happen regardless of what you choose is [[spoiler:Solas]] who breaks up with the Inquisitor, and she is unable to romance anyone else since they can't move on from it.
* ''Franchise/FinalFantasy'':
** ''VideoGame/FinalFantasyX'': At the very end, [[spoiler:Yuna doesn't get the guy; he never existed in the first place, technically]]. Can be averted in the best ending of ''X-2'', [[spoiler:where the Fayth use the last of their power to incarnate Tidus for real]].
** Zig-Zagged in ''VideoGame/FinalFantasyAdventure'' - the player would ''think'' that once they beat the FinalBoss and restore peace to the land, the boy and the girl would get together... except [[spoiler: the mana tree vanishes, so the girl has to become the BarrierMaiden to the world]]. ''VideoGame/SecretOfMana'' however, implies that [[spoiler: somehow he did, as the mana tree is the main character's mother, and his DisappearedDad was the last Gemma knight: the PC in ''VideoGame/FinalFantasyAdventure'']].
* In ''VideoGame/FireEmblemTheBlazingBlade'':
** This happens with ''two'' of Priscilla's potential love interests, as her noble status prevents her from being able to continue a relationship with both Guy, a poor swordsman, and Heath, a Wyvern Knight deserter. Sain is another potential partner, but his duties to his kingdom prevent him from leaving for her and their support chat ends with them coming to this realization. Erk, her ''fourth'' option, is the only one that actually ''can'' stay with Priscilla due to him having friends in high places.
** Harken and Vaida must part ways due to their dedication to their respective lords.
** Marquess Araphen lost his fiancee when she chose instead to elope with a Sacaean nomad. Which led to Marquess Araphen's FantasticRacism.
* Ike and Elincia in ''VideoGame/FireEmblemPathOfRadiance'', despite a decent amount of ShipTease between them. By the sequel, the chemistry between them is nonexistent and Elincia's feelings have shifted towards [[BodyguardCrush Geoffrey]] (and possibly [[HoYay his sister Lucia]]). This is mostly the result of [[DubText the English dub adding hints toward the pairing]] when the original Japanese portrayed them as strictly platonic, but being forced to back off when the sequel had a different OfficialCouple.
* ''VideoGame/FullThrottle'' has the woman-not-getting-man version when Mo takes over Corley Motors, thus losing access to the free-roaming lifestyle that would have kept her together with Ben.
* ''VideoGame/KnightsOfTheOldRepublic'' and the sequel has both [[spoiler:Revan]] and [[spoiler:the Jedi Exile]] vanish into the Unknown Regions to seek out the old Sith Empire to finish the fight, leaving behind a love interest (and all their allies, for that matter) in both cases. It's later revealed in ''Literature/{{Revan}}'' that [[spoiler:Revan ''did'' get the girl; he and Bastila were married between the two games, and she was pregnant with his son when he vanished (on a trip that was supposed to only be temporary)]].
* ''VideoGame/TheLastOfUsPart2'': Ellie has a chance to settle down and make a happy life for herself with her true love Dina and her son, after their brutal campaign of revenge against [[spoiler: Joel's murderers]] has concluded. However, [[spoiler: Joel's brother Tommy shows up and guilt trips Ellie about how she let the one most responsible, Abby, live and accuses her of breaking the promise to kill her. Ellie eventually decides to finish the job. Dina, who is tired of the senseless violence gives Ellie an ultimatum, life with her or revenge against Abby. Ellie chose revenge and loses Dina for good, which the ending makes clear when she returns to an empty farmhouse where they were staying.]]
* ''VideoGame/{{Lyrica}}'': Du Mu really has bad luck in his romance. First, he falls in love with a beautiful dancer named Zhang Haohao, but her employer took her as a concubine before he could make any moves on her. Then he meets Shiue and falls for her, but of course he can't be with her since she doesn't exist in his timeline. He manages to encounter a girl [[IdenticalStranger who looks almost exactly like Shiue]] and wants to marry her, but she's too young for that. After forming an agreement with the girl's family to marry her within ten years, he fails to return at the allotted time (thus voiding the agreement), and the girl marries someone else.
* One of two endings to ''VideoGame/MetalGearSolid'' shows Snake and Meryl riding off together into the sunset. In the sequel, she's nowhere to be found. The book written by Nastasha makes it canon that she survived, but the only reference to her in the game proper is some optional dialogue where Snake says he's had enough of tomboys. Cue the fourth game where [[spoiler:Snake's an old man and Meryl gets married to the very guard she knocked out at the beginning of the first game. (See CartwrightCurse.) In addition, it ''seems'' like this in Raiden's case but it's later subverted when it's revealed it was a cover story he wasn't in on]]. [[spoiler: This is justified for Snake's case, however. Being a clone, Solid Snake is [[CelibateHero sterile]], and he [[LaserGuidedTykebomb carries a modified virus created by Naomi]], which randomly kills people injected with {{nanomachines}}. In short, he is essentially a '''[[WeaponOfMassDestruction walking]] [[TheVirus FOXDIE]]''' and is too dangerous to have a relationship with anyone.]] See also Ellen Madnar and Holly White from the first two games.
* ''VideoGame/NeverwinterNights: Hordes of the Underdark'' reveals that the Hero of Neverwinter was good, male, and completed the romance subquest with Aribeth. Then [[spoiler:Aribeth was executed for treason with the Hero protesting every step of the process and the Hero leaves the city, estranged from its lords and his friends]]. The fan-made module ''VideoGame/TheBastardOfKosigan'' has the hero's former {{love interest|s}} die an unavoidable death at the hands of French assassins, even if you attempt to renew your relationship with her.
* ''VideoGame/NeverwinterNights2''. Both possible LoveInterests die in the collapsing fortress at the end, unless you drove Elanee off.
* ''Franchise/{{Persona}}'':
** While the ending of ''VideoGame/{{Persona 2}}: Innocent Sin'' is an example of [[BittersweetEnding that other trope]], ''Eternal Punishment'' plays this straight as [[spoiler: Tatsuya ends up returning to the Other Side, and if Maya ever gets involved with This Side's Tatsuya there'd be a risk of screwing over the world again, so seeing him or his brother isn't really an option either. The ending movie has Maya accepting this and walking by Tatsuya without saying anything]]. In fact, this is built into the title of the games; this is Tatsuya's "Eternal Punishment" for the "Innocent Sin" that he committed during the first game.
** The Protagonists do not get the girls/guys in ''VideoGame/{{Persona 3}}''. [[spoiler: A HeroicSacrifice to become the BarrierMaiden for the world can do that.]]
* The ''VideoGame/PrinceOfPersia2008'': ''Epilogue'' ends on this note. After an entire game's worth of semi-witty WillTheyOrWontThey sexual tension, Elika finally has enough and literally runs off on the Prince [[spoiler:because he freed the [[EldritchAbomination God of Darkness]] who they spent the entire time trying to seal away, on the misguided notion that he could bring Elika back to life and use her to defeat it once and for all. Only, she didn't think she could, and didn't want to even try]]. [[NiceJobBreakingItHero Nice Job Breaking It, Dumbass]].
* ''VideoGame/RedDeadRedemption2'': [[UptownGirl Mary Linton]] loves Arthur Morgan dearly but doesn't want to be with him while he's still riding with a gang. He promises once he gets enough money he will run away with her. [[spoiler:Though she still loves him, she breaks things off with him for good via a "Dear John" letter once word reaches her of the gang's botched robbery at Saint Denis. Tragically, Arthur is in the final stages of tuberculosis by the time he receives the letter, and before he can patch things up with her, he either gets killed by [[BigBad Micah Bell]] (low honor) or succumbs to the disease (high honor). She is seen in the credits crying at his grave.]]
* ''VideoGame/ShadowHearts'' does this a few times. The Canonical ending of the first ends with [[spoiler: Alice dying, meaning Yuri did not get the girl after all]]. However, Yuri's next apparent love interest, Karin, [[spoiler: Was sent into the past, meaning she did not get the guy....instead becoming his mother]]. But, the StableTimeLoop allows Yuri to [[spoiler: earn his happy ending]] after all.
* ''VideoGame/SoulSeries'': According to the ''Soulcalibur V'' profile for Leixia (daughter of Xianghua), her father is ''not'' Kilik, her {{love interest|s}} for the previous four games.
* At the end of ''VideoGame/SuperMarioOdyssey'', [[spoiler:Mario tries to propose to Princess Peach, but Bowser butts in and they get caught up in a squabble over her and end up just shoving flowers in her face. Annoyed by their immaturity, Peach shoots them down and preserves the {{status quo|IsGod}}]].
* In ''VideoGame/TalesOfXillia'':
** Jude did not get Milla [[spoiler: because she had to AscendToAHigherPlaneOfExistence]].
** Despite their history together, Alvin did not get to be with [[spoiler: Presa]]. Same with Rowen and [[spoiler: Nachtigal's sister, whom he was engaged to. She was presumed dead during an accident, but can be found later alive and healthy, but suffering from Amnesia, with no memories of Rowen, and she is HappilyMarried]].
* ''VideoGame/TalesOfXillia2'':
** A case can be made for Ludger and Alternate Milla, with heavy implications that Milla had feelings for Ludger. Likely a case of ForegoneConclusion, as being part of a fractured dimension means she was never supposed to be in the prime dimension to begin with. [[spoiler: And she ultimately has to die, in order for the prime dimension's Milla to return and brings things back in order.]]
** Just as with the previous game, [[spoiler: Jude and Milla still cannot remain together, as Milla can only remain in the Human Realm for a limited time now]]. Same can be said for [[ShipTease Gaius and Muzét]] or Ludger and Muzét, with the former admitting in his diary that he has a crush on her, though how severe this case is debatable; Muzét is the only Great Spirit who can freely walk between the Spirit and Human Realm.
* ''[[VideoGame/TronTwoPointOh Tron 2.0]]'': While it's clear Jet and Mercury were attracted to one another, he has to return to analog, and she has to stay in the digital world. Poor guy got his HonoraryUncle's luck.
* Towards the end of ''VideoGame/WolfensteinTheNewOrder'', [[spoiler:B.J. Blazkowicz realizes that as long as the Nazis still remain, he can not get Anya]], and instead allows her to TakeUpMySword for the war to come, knowing that he'll likely die in the battle against Deathshead. [[spoiler:[[TheHeroDies Which he does]], unless the sound of an approaching helicopter means that NoOneGetsLeftBehind]]. Averted in the sequel, ''VideoGame/WolfensteinIITheNewColossus'', where BJ gets rescued, Anya is pregnant, and [[spoiler:against all odds, lives to the end of the game and proposes to Anya in the ending]].
* ''VideoGame/{{Yakuza 0}}'': Goro Majima is sent to assassinate someone named Makoto Makimura, which turns out to be more complicated than it seems when Makoto turns out to be an innocent blind girl whom everyone wants dead or in their possession for reasons neither of them knows. Majima decides to protect Makoto and starts to become attracted to her, but when she's injured near the climax he realizes life around a gangster like him would not end well for her, so he leaves quietly and instructs the doctor who saved Makoto's life to look after her. When they reunite eighteen years later in ''Kiwami 2'', Makoto is HappilyMarried with a son, and Majima stays quiet during their massage session so she won't recognize who he is (though he slips her a personal gift to tip her off so she could get some closure with the man who saved her life).
* Adol in the ''VideoGame/{{Ys}}'' series, almost every time. Of course, apart from Feena in [[VideoGame/YsIAncientYsVanishedOmen I]]/[[VideoGame/YsIIAncientYsVanishedTheFinalChapter II]], it was more like the various girls Did Not Get The Guy.
[[/folder]]

[[folder:Visual Novels]]
* In ''VisualNovel/NineHoursNinePersonsNineDoors'', [[spoiler:Akane and Aoi]] flee Building Q before [[spoiler:Junpei]] can catch up to them. He spends the rest of his days trying to [[spoiler:find Akane]]. The sequel, ''VisualNovel/VirtuesLastReward'', really hammers it in by showing [[spoiler:Junpei as an old man, now going by Tenmyoji]], ''still'' trying. [[spoiler:Though he does succeed in this game, Akane is so far removed from what he remembers that he gives up on her.]] As for the third game, ''VisualNovel/ZeroTimeDilemma'', which takes place between the first two... [[spoiler:Thanks to time travel, the trope is finally averted and Junpei and Akane get together in the GoldenEnding.]]
* ''VisualNovel/FateStayNight'':
** Fate route: In the most tear-jerking way, Shirou has to part with Saber and life moves on. [[spoiler:However, in Realta Nua's bonus ending of Fate they [[TogetherInDeath meet again]].]]
** Two of the bad endings in Heaven's Feel result from the heroine of the route, Sakura, being killed while Shirou is still alive and well. If [[spoiler:Shirou]] kills Sakura, Shirou destroys his remaining humanity to pursue [[TheNeedsOfTheMany Kiritsugu's dream]]; if [[spoiler:Rin]] kills Sakura, Shirou is [[DespairEventHorizon driven to despair]] due to previously surrendering his dream to protect Sakura.
* In ''[[http://lemmasoft.renai.us/forums/viewtopic.php?f=11&t=19865 Get Dumped]]'', no matter what you do, Michi will be unable to convince Arashi to stay with her and the true ending has her realize that she was LovingAShadow.
* Can happen in ''VisualNovel/{{Melody}}'' if the player steers clear of the romantic paths of ''all'' the girls.
[[/folder]]

[[folder:Web Animation]]
* ''WebAnimation/{{RWBY}}'':
** At the end of Volume 3, [[spoiler:Jaune and Pyrrha become an OfficialCouple, and then about 15 minutes later, Pyrrha dies fighting [[TheHeavy Cinder]]]].
** Later on, in Volume 5, [[spoiler:part of the reason why Ilia [[ThenLetMeBeEvil embraced villainy]] was out of jealousy towards Blake's relationship with Adam. Although Ilia pulls a HeelFaceTurn and fixes her friendship with Blake, even helping her stop Adam's attack on Haven, Blake leaves for Atlas in Volume 6. Ilia, at least, is thankful for being given a second chance]].
[[/folder]]

[[folder:Webcomics]]
* In ''Webcomic/{{Katamari}}'' (a comic based on ''VideoGame/KatamariDamacy'') had a story arc revolving around the Prince of Cosmos helping a man try to regain his girlfriend by rolling up a katamari of all the things she likes as a show of affection. However, when presented with it, she shows she's flattered by the gesture but lets him down gently that she isn't interested in pursuing the relationship.
* Despite the effort Shigeo puts trying to become someone his longtime childhood crush might be interested in over the course of the series, ''Webcomic/MobPsycho100'' ends with Tsubomi politely but soundly turning him down. [[spoiler:Six months later, he's over it and probably happier than he's been in ages anyway, since all the CharacterDevelopment he had on the way makes it so much easier for him to stop withdrawing into himself and actually connect with people.]]
* ''Webcomic/ThePhoenixRequiem'' ended with [[spoiler:Jonas and Anya splitting over his need to become the Grim Reaper. Though the ending left it ambiguous as to whether it would stay that way for good]].
[[/folder]]

[[folder:Web Original]]
%%* ''WebVideo/DoctorHorriblesSingAlongBlog'' plays this straight and in the most tragic fashion possible.
* Creator/FreddieWong in the action short "Gun Size Matters," leading to a hilarious live-action version of OcularGushers.
* ''Literature/TheKindnessOfDevils'': This is one of Hardestadt Delac's personal problems throughout the series. He's immortal, and all the women he's dated have either been killed during his various conquests or simply died of old age. ''Literature/LovesLostAndFound'' shows more than half a dozen of Delac's wives or lovers that he's had over the course of ''centuries'', and all of them (except Erin and Eliza) all died off-screen at some point.
* Gender-inverted in ''WebAnimation/NekoSugarGirls''. Raku's LoveConfession to Hitoshi-san fails because [[spoiler:he is dating Kidnapper-kun. Raku then dies due to her heart breaking]].
* ''Machinima/RedVsBlue'':
** While Tex does not die at the end of the series, neither is Church able to keep her in his life.
** Agent York of Project Freelancer had feelings for Agent Carolina. [[spoiler: Too bad he thought she was killed by the Meta and he was killed before she was revealed to still be alive.]]
[[/folder]]

[[folder:Western Animation]]
* ''[[WesternAnimation/{{Sixteen}} 6Teen]]'': Jude with Starr when the latter decided to go goth.
* The last episode of ''WesternAnimation/AdventureTime'' not only [[spoiler: doesn't have Finn hook up with anyone, but Simon loses Betty who sacrifices herself]]. Subverted in the post-finale comics: [[spoiler:[[ComicBook/AdventureTimeSeason11 the Season 11 comic]] implies that Finn and Huntress Wizard are still dating while [[ComicBook/AdventureTimeMarcyAndSimon Marcy and Simon]] ends with Simon and Betty being reunited thanks to Hunson]].
* Steve from ''WesternAnimation/AmericanDad'' is a poster boy for this trope as the episodes where he tries to get the girl always ends like this because StatusQuoIsGod. His longest relationship is with Debbie who dumped him in "Bar Mitzvah Hustle" (''twice''). When he dates Akiko (Toshi's sister), she disappears without mention in the next episodes and Steve has gone back to being single.
* ''WesternAnimation/BatmanBeyond'': Throughout the Franchise/DCAnimatedUniverse, Bruce Wayne has had many love interests: [[Characters/CatwomanSelinaKyle Catwoman/Selina Kyle]], ComicBook/{{Zatanna}} (one-sided only, Bruce always considered them JustFriends), [[Characters/BatmanRasAlGhul Talia Al-Ghul]], [[WesternAnimation/BatmanMaskOfThePhantasm Andrea Beaumont]], Characters/{{Wonder Woman|TheCharacter}}, Barbara Gordon/ComicBook/{{Batgirl}}... He doesn't end up with any of them and remains a single, old man.
-->'''Bruce Wayne:''' When I was young, [[ChickMagnet women used to throw themselves at my feet all the time]].\\
'''Terry [=McGinnis=]:''' What did you do?\\
'''Bruce Wayne:''' [[CelibateHero Step over them]].\\
'''Terry [=McGinnis=]:''' Smooth.\\
'''Bruce Wayne:''' I thought so.
* A gender-reversed version happens in ''WesternAnimation/FamilyGuy'' with Meg twice with both Joe's son and the nudist boy. She does get Neil but then drives him away when he proves annoying.
* In ''WesternAnimation/{{Gargoyles}}'', the young trio vie for the affections of Angela until it gets irritating that she demands they stop, roaring "The winner does not get to keep me!" Ultimately, she falls for Broadway, leaving Brooklyn heartbroken while Lexington is occupied elsewhere.
* The last episode of ''WesternAnimation/GravityFalls'' [[spoiler:doesn't show Dipper hooking up with anybody]]. There were already episodes devoted to the ShipSinking of him with Wendy and Candy.
* ''WesternAnimation/TheLegendOfKorra'': Mako messes up both his relationships with [[TomboyAndGirlyGirl Korra and Asami]] by the end of book 2. So much so that by the end of the GrandFinale, [[spoiler: he's the only one without a girlfriend of the main group. His brother [[BigFun Bolin]] ends up with [[BadAssAdorable Opal]]. Even ''Korra and Asami'' have girlfriends: [[PairTheSuitors each other]].]]
* At the end of ''WesternAnimation/RegularShow'', Mordecai doesn't end with either Margaret or Cloudy Jay, partly due to the former focusing on her career and the latter breaking things off when she ''thinks'' Mordecai might still have a feeling for Margaret (ironically when he was trying to confess his feelings for her during Muscle Man's wedding). Partly due to the whole being unwillingly blasted off into space for several years to save the universe. Once they return to Earth, he decides to focus on his own career as an artist and meets a bat woman during one of his art exhibits. The finale seeing that he ultimately married her and had many children.
* ''WesternAnimation/SamuraiJack'': [[spoiler:Jack and Ashi fall in love, but him killing her father Aku in the past causes her to [[RetGone fade from existence]]]].
* ''WesternAnimation/ScoobyDooMysteryInc'': Shaggy and Velma have hooked up prior to the series' beginning, [[spoiler: but he breaks it off with her when he thinks it means it'll jeopardize his and Scooby's friendship. She remains quite bitter about this for a while]]. This also happened with Ricky Owens and Cassidy Williams (a.k.a. Mr. E and Angel Dynamite), [[spoiler: but in the GrandFinale's new timeline, they are HappilyMarried]].
* Peter in ''WesternAnimation/TheSpectacularSpiderMan,'' due to premature cancellation. The season two finale ends with [[spoiler:Gwen remaining with Harry out of pity]].
* ''WesternAnimation/SpiderMan1981'': The last episode "Under the Wizard's Spell", Spidey gets close with Inhuman Medusa and the two share a kiss at the end. She has to return home, leaving Peter heartbroken.
* Lampshaded in ''WesternAnimation/SpiderManTheAnimatedSeries'' at the end of the episode that introduced Kraven, where Peter complains to himself that it's supposed to be the hero (him) that gets the girl, not the reformed villain (Kraven).
* Beast Boy and Cyborg in ''WesternAnimation/{{Teen Titans|2003}}''. [[spoiler: With Beast Boy: first Terra had a FaceHeelTurn; then a HeelFaceTurn that resulted in her being [[TakenForGranite turned to stone]]; then she may or may not have been brought back to life, but either way Beast Boy lets her go. With Cyborg: he and Sarasim do kiss, but he's transported back into the future soon after since they do come from different times. He knows that she survived the battle, though.]] In the ''ComicBook/TeenTitansGo'' tie-in comics, however, [[spoiler: Cyborg ''does'' gain a girlfriend in Sarah, a caretaker for a group of handicapped kids, both of which are first seen in the episode "The Sum of His Parts."]]
* PlayedForDrama in ''WesternAnimation/ThunderCats2011'' for RebelPrince and royal heir Lion-O.
** He develops a [[BodyGuardCrush crush]] on Cheetara, a woman he discovers is a member of his ChurchMilitant PraetorianGuard, he realizes his [[TheLancer Lancer]] brother Tygra, also has [[HotForPreacher feelings]] for her. As they set off on a shared journey, the two develop a passive-aggressive, increasingly toxic SiblingTriangle rivalry for her affections to which she remains largely [[ObliviousToLove oblivious]], with both brothers interpreting the attention she pays Lion-O as romantic interest. After they come to blows over her, Cheetara takes Tygra aside and apologizes for failing to confess her feelings. She and Tygra share a [[ChildhoodFriendRomance childhood history]], and she's carried a torch ever since he did her a favor that helped her join the Clericy. They kiss just as Lion-O walks into view, confident he's avoided a prophecy foretelling Tygra's betrayal.
** He attempts to move on when he meets Pumyra. Though their relationship is rocky at best, as she originally blames Lion-O for the fall of Thundera, he's able to help bring out her good side. As time progresses, the two become close. [[spoiler:However, it's revealed she faked her budding relationship and is [[SixthRangerTraitor working for Mumm-Ra]] to kill Lion-O, her vengeance being more important.]] He's heartbroken afterwards.
** WordOfGod says had the show continued, he would have found love with [[spoiler:an aged-up Wilykit]].
* ''WesternAnimation/TotalDrama'':
** Cody loses Gwen to another guy ''twice.'' It's possible he [[HookedUpAfterwards Hooks Up Afterwards]] with [[StalkerWithACrush Sierra]], though at the end of season three he insists they remain JustFriends.
** Dave in ''Pahkitew''. Especially after finding out that the "girl" (Sky) already has a boyfriend, upon which his SanitySlippage gets even worse than it already was.
[[/folder]]

* Inevitable in nearly all installments of ''Anime/WeissKreuz'' due to the protagonists being {{Doom Magnet}}s - the few potential love interests who don't end up dead get the ItsNotYouItsMyEnemies treatment. The only exception here is ''Farfarello'', who leaves with his love interest at the end of the Schwarz audio drama to lead a happy, kill-free life.

* ''ComicBook/LesAiglesDeRome'': Marcus survives the Battle of Teutoburg Forest and his romantic rival Lepidus is taken out, but Priscilla is raped and decapitated while his son Titus is enslaved by the Germans.

* Spike in ''FanFic/BeneathYourFeetWhatTreasures''; the story is about him dealing with his feelings towards Rarity via his treasure hoard, along with his knowledge that he will never get the girl.

* Occasionally happens in the Literature/JackReacher novels. [[spoiler:''Die Trying'' is an example; while Reacher and the female lead have a mutual attraction and once engage in GladToBeAliveSex, she is in love with someone else and moves in with (and possibly marries) him at the end of the novel]].

* In ''ComicBook/{{Drama}}'', Callie is attracted to twin brothers Justin and Jesse but ends up with neither of them because Justin [[SorryImGay turns out to be gay]] and Jesse [[spoiler:''also'' turns out to be gay]]. There's a third boy who expresses interest in Callie, but she turns him down and is still single at book's end.

** In ''Literature/TheSandman'' Nathaniel doesn't end up with his childhood sweetheart Clara nor the other girl who he fell for that happened to be a robot. Oops.

* The [[Anime/FullmetalAlchemist 2003 anime version]] of ''Manga/FullmetalAlchemist'' ends this way (''twice''): in the TV ending, [[spoiler: Ed is [[TrappedInAnotherWorld trapped in our world]] searching for a way to get back while Winry and Rose are left behind]], and in TheMovie ''Anime/FullmetalAlchemistTheConquerorOfShamballa'' [[spoiler:after finding a way back to Amestris and reuniting with Winry, he realizes that our world needs him more than Amestris and seizes his last chance to return and seals off the portal connecting the two worlds for good, leaving Winry behind yet again]].

* In ''Anime/PrincessMononoke'', Ashitaka and San fall in love. However, at the end, they realize that neither of them could give up their lives for each other, and the two part, promising to still meet as friends.

** Kamina dies shortly after he and Yoko admit their feelings towards each other.

** The heroine, Hitomi, chooses to go back to Earth while Van stays behind in Gaia to help his world heal from the war it just endured. Despite the show being [[ExecutiveMeddling dramatically cut down]] from its planned run, that was the intended ending all along.

* ''Manga/YourLieInApril'' ended with Kousei and Kaori not ending up together. [[spoiler:Kaori ''did'' love him but he didn't learn this until he read her [[DeadManWriting posthumous letter]].]]

[[quoteright:350:[[WesternAnimation/TheHunchbackOfNotreDame https://static.tvtropes.org/pmwiki/pub/images/hunchback_didnotgetthegirl.png]]]]

** The Disney version of ''WesternAnimation/TheHunchbackOfNotreDame'', which is featured as the image of this page. Unlike most of the lead males of the Disney Renaissance, Quasimodo doesn't end up with the woman he falls in love with. Namely, Esmeralda never learns of his feelings and falls for Phoebus, [[IWantMyBelovedToBeHappy though Quasimodo chooses to accept that she loves him without issue]]. He eventually gets together with another woman in the [[WesternAnimation/TheHunchbackOfNotreDameII sequel]], though.

* In the ''Manga/DeathNote'' fanfic ''Fanfic/StoryOfTheCentury'', [[spoiler: Light ends up dying on Misa after they're caught; before then she gives him an AnguishedDeclarationOfLove that [[UngratefulBastard he doesn't even acknowledge.]] On the other hand L, [[HeroicSacrifice having given up his own life to expose the two Kiras]], [[ShooTheDog forces Erin to leave so that he can be alone when he dies.]] Her last words to him are a long and vicious TheReasonYouSuckSpeech that [[BreakTheHaughty he takes rather gracefully]] and while neither of them outright say how they feel, his final gesture communicates his real feelings. Only after she goes home does Erin [[ObliviousToLove figure out his feelings and hers]], and [[PartingWordsRegret she is seen struggling with this for a long time, among other things, in the epilogue]]]].

* Towards the end of ''VideoGame/WolfensteinTheNewOrder'', [[spoiler:B.J. Blazkowicz realizes that as long as the Nazis still remain, he can not get Anya]], and instead allows her to TakeUpMySword for the war to come, knowing that he'll likely die in the battle against Deathshead. [[spoiler:[[TheHeroDies Which he does]], unless the sound of an approaching helicopter means that NoOneGetsLeftBehind]].

* Both of the books in Marti Steussy's "First-In" duology have {{bittersweet|Ending}} gender-flipped examples. In ''Forest of the Night'', [[spoiler:Gaylord Hess]] spurs the conflict between humanity and the [[IntelligentGerbil Lodgeless Ones]]; by the time he gets a clue, his agitation has caused several deaths on each side and it's clear that he's never going to fully appreciate or understand Hashti's position. In ''Dreams of Dawn'', [[spoiler:Aage]] is simply too reluctant to compromise on the dilemma regarding the world's MirrorChemistry, leading Disa to ultimately distance herself from him. ''Forests'' leaves [[spoiler:Gaylord's and Hashti's]] romantic futures ambiguous[[spoiler:; the DistantFinale of ''Dreams'' gives both Disa and Aage {{Second Love}}s: another young First-In member for Disa, and the [[GirlNextDoor sweet local girl Gretchen]] for Aaage]].

* Both of the books in Marti Steussy's "First-In" duology have {{bittersweet|Ending}} gender-flipped examples. In ''Forest of the Night'', [[spoiler:Gaylord Hess]] spurs the conflict between humanity and the [[IntelligentGerbil Lodgeless Ones]]; by the time he gets a clue, his agitation has caused several deaths on each side and it's clear that he's never going to fully appreciate or understand Hashti's position. In ''Dreams of Dawn'', [[spoiler:Aage]] is simply too reluctant to compromise on the dilemma regarding the world's MirrorChemistry, leading Disa to ultimately distance herself from him. [[spoiler:Both eventually find {{Second Love}}s — another young First-In member for Disa, and the [[GirlNextDoor sweet local girl Gretchen]] for Aaage.]]

** In ''[[Anime/LupinIIIIslandOfAssassins Island of Assassins]]'', he tried hitting on [[BrokenBird Ellen]], though it was mainly just fun 'n games for him, until he learned how she became part of [[MurderInc the Tarantulas.]] She was initially put-off by his attempts to flirt with her because she didn't trust him. By the end of the film, her opinion of him had changed, but only so far as thanking him for giving her a brief moment of freedom. [[spoiler: Said with her dying breath]].

* Meowth in the ''Anime/PokemonTheOriginalSeries'' episode "Go West, Young Meowth", who tries to help his love interest who spurned him in the past. He defeats his long hated rival Persian but the girl Meowth chooses the Persian over him anyway.

* Hazuki from ''VisualNovel/YamiToBoushiToHonNoTabibito'' never gets her girl Hatsumi, at least in the anime, despite her valiant efforts of chasing her through several alternate dimensions. It is heavily implied that Hatsumi grants Hazuki one night with her, but then erases her memory afterward, which caused quite a bit of outrage among {{yuri fan}}s.

* Played with in a very gruesome way in ''ComicBook/LesLegendaires'' during the Anathos Cycle. As the protagonists prepare to fight the GodOfEvil Anathos, [[TheHero Danael]], feeling tired with everything that happened so far, eventually fully confess his feeling to [[MagicalGirl Jadina]] once and for all, and proposes her to marry after the fight. She agrees and they share a kiss... [[spoiler:then after the fight, Anathos ends up [[DemonicPossession taking over Danael's body]]. When the heroes finally defeat Anathos at the end of the Cycle, Jadina is forced to stab Danael in order to succeed. Though he's then resurrected, he has left the group and is convinced to leave the past behind him, while Jadina replaces him as TheHero.]]

** Susan Rodriguez was the steadiest girlfriend he had, and they were genuinely in love. [[spoiler:Literally; Susan's love for Harry protects him from the White Court.]] Unfortunately, [[spoiler:bad decisions on both their parts ended with Susan becoming a half-vampire and forced to go on the run for the rest of her life, though not without carrying Harry's child]]. In the end, [[spoiler:[[ADeathInTheLimelight Harry ends up killing her]] to trigger a bloodline curse that kills all of the Red Court vampires in the world]]. Ouch....

* ''Literature/HollowPlaces'' features a variation of this trope. Austin does end up with Isabella, but by then she's so different from the woman he fell in love with she could hardly be called the same person.

** They do get a somewhat happy ending at the end of Series 4. Due to a complicated series of events wherein the Doctor undergoes a partial regeneration which he aborts by channelling into his [[ChekhovsGun spare hand]], the hand later grows into a Half-Human clone of the Doctor after absorbing some of Donna's DNA. The Doctor decides to leave his doppelganger with Rose in the alternate-universe, knowing that he can grow old with her and give her a life that he never could.

** Generation 1 ends inconclusive whether Sid reunited with Cassie in the US. "Skins Pure" reveals that they did not get together again.

* ''VideoGame/TheLastOfUsPart2'': Ellie has a chance to settle down and make a happy life for herself with her true love Dina and her son, after their brutal campaign of revenge against [[spoiler: Joel's murderers]] has concluded. However, [[spoiler: Joel's brother Tommy shows up and guilt trips Ellie about how she let the one most responsible, Abby, live and accuses her of breaking the promise to kill her. Ellie eventually decides to finish the job. Dina, who is tired of the senseless violence gives Ellie an ultimatum, life with her or revenge against Abby. Ellie chose revenge and loses Dina for good, which the ending makes clear when she returns to an empty farm house where they were staying.]]
* ''VideoGame/{{Lyrica}}'': Du Mu really has a bad luck in his romance. First, he falls in love with a beautiful dancer named Zhang Haohao, but her employer took her as a concubine before he could make any moves on her. Then he meets Shiue and falls for her, but of course he can't be with her since she doesn't exist in his timeline. He manages to encounter a girl [[IdenticalStranger who looks almost exactly like Shiue]] and wants to marry her, but she's too young for that. After forming an agreement with the girl's family to marry her within ten years, he fails to return at the allotted time (thus voiding the agreement), and the girl marries someone else.

** Fate route: In the most tearjerking way, Shirou has to part with Saber and life moves on. [[spoiler:However, in Realta Nua's bonus ending of Fate they [[TogetherInDeath meet again]].]]

* ''WesternAnimation/TheLegendOfKorra'': Mako messes up both his relationships with [[TomboyAndGirlyGirl Korra and Asami]] by the end of book 2. So much so that by the end of the Grand Finale [[spoiler: he's the only one without a girlfriend of the main group. His brother, [[BigFun Bolin]] ends up with [[BadAssAdorable Opal]]. Even ''Korra and Asami'' have girlfriends, each other. ]]

* As a young man, Franchise/{{Superman}} never married his college love [[OurMermaidsAreDifferent Lori Lemaris]], who turned down his proposal and finally married someone else. Of course, Supes eventually fell in love with [[Characters/SupermanLoisLane Lois Lane]] and even managed to stay friends with Lori, so it all worked out okay.

* ''Series/{{Smallville}}'' - [[ForegoneConclusion It should be extremely obvious]] to anyone with even a passing knowledge of Franchise/{{Superman}} lore that Clark and Lana do not end up together.

* The last episode of ''WesternAnimation/AdventureTime'' not only [[spoiler: doesn't have Finn hook up with anyone, but Simon loses Betty who sacrifices herself]].
** Subverted in the post-finale comics: [[spoiler:[[ComicBook/AdventureTimeSeason11 the Season 11 comic]] implies that Finn and Huntress Wizard are still dating while [[ComicBook/AdventureTimeMarcyAndSimon Marcy and Simon]] ends with Simon and Betty being reunited thanks to Hunson]].

* ''WesternAnimation/BatmanBeyond'': Throughout the Franchise/DCAnimatedUniverse, Bruce Wayne has had many love interests: [[Characters/BatmanCatwoman Catwoman]]/Selina Kyle, ComicBook/{{Zatanna}} (one-sided only, Bruce always considered them JustFriends), ComicBook/TaliaAlGhul, [[WesternAnimation/BatmanMaskOfThePhantasm Andrea Beaumont]], Franchise/WonderWoman, Barbara Gordon/ComicBook/{{Batgirl}}... He doesn't end up with any of them and remains a single, old man.

* Beast Boy and Cyborg in ''WesternAnimation/TeenTitans''. [[spoiler: With Beast Boy: first Terra had a FaceHeelTurn; then a HeelFaceTurn that resulted in her being [[TakenForGranite turned to stone]]; then she may or may not have been brought back to life, but either way Beast Boy lets her go. With Cyborg: he and Sarasim do kiss, but he's transported back into the future soon after since they do come from different times. He knows that she survived the battle, though.]] In the ''ComicBook/TeenTitansGo'' tie-in comics, however, [[spoiler: Cyborg ''does'' gain a girlfriend in Sarah, a caretaker for a group of handicapped kids, both of which are first seen in the episode "The Sum of His Parts."]]
* PlayedForDrama in ''WesternAnimation/Thundercats2011'' for RebelPrince and royal heir Lion-O.

* Tony and Michelle in ''Series/{{Skins}}'' end up going their separate ways because of different universities.

** Along with Angel and [[DeadAllAlong Cordelia]], [[IDidWhatIHadToDo Gunn]] and Fred, and Wesley and [[DemonicPossession Fred]] all of Series/{{Angel}}

* Despite the effort Shigeo puts trying to become someone his longtime childhood crush might be interested in over the course of the series, ''Manga/MobPsycho100'' ends with Tsubomi politely but soundly turning him down. [[spoiler:Six months later, he's over it and probably happier than he's been in ages anyway, since all the CharacterDevelopment he had on the way makes it so much easier for him to stop withdrawing into himself and actually connect with people.]]

!!Examples:

[[folder:Films -- Live-Action]]
%%* ''Film/FiveHundredDaysOfSummer''. It's right there in the title.
* The protagonist of ''Film/{{Adam}}'' doesn't end up with his love interest.
* ''Film/AnnieHall'' ends with the main characters realizing they're BetterAsFriends.
* Toward the end of Harold Ramis' remake of ''Film/{{Bedazzled|2000}}'', the hero finally finds the courage to ask out his love interest. As it turns out, she's seeing someone. This is actually a plot point: at the beginning of the movie the main character mentions that she's recently split up with her [unseen] boyfriend, and [[spoiler:his final wish, that [[IJustWantMyBelovedToBeHappy she have a happy life]], apparently undoes the break-up]]. He handles it admirably, given what he's been through. Although, bizarrely, the hero ''does'' then end up with another, kookier, more down-to-earth girl who is ''played by the same actress''.
* In Creator/TimBurton's ''Film/BatmanReturns'', Batman did not get to be with Catwoman in the end, though she is hiding right behind his back.
-->'''Catwoman:''' Bruce...I'd love to live with you in your castle forever, like in fairy tales. NO! I just couldn't live with myself! So ''don't'' pretend this is a happy ending!
* Jack Burton [[InvertedTrope inverts]] this by rejecting the advances of the girl and returning to being a loner after getting his truck back at the end of ''Film/BigTroubleInLittleChina''. As Ol' Jack Burton puts it: ''"Sooner or later, I rub everybody the wrong way."''
* In ''Film/{{Brick}}'' Brendan's first love interest dies at the beginning, and his second [[spoiler: turns out to have orchestrated her murder]].
* An unusual version is done in ''Film/TheBrothersGrimm'' - both of the brothers love Angelika and both [[spoiler:get a kiss with her at the end]], but she never actually hooks up with either of them. This is even lampshaded.
-->'''Jacob:''' I always thought that you would end up with the girl.\\
'''William:''' Well you see that? ''(Points up.)''\\
'''Jacob:''' What, the sun?\\
'''William:''' The day is not over yet!
* In the theatrical ending to ''Film/TheButterflyEffect'', after many failed attempts to SetRightWhatOnceWentWrong, Evan realizes the only way for Kayleigh to be happy is to [[spoiler:prevent them from ever befriending each other so that she and her brother would choose to live far away with their mom instead of their sexually abusive father. Evan runs into Kayleigh in a downtown street in New York, but he ignores her after hesitating for a moment]].
* ''Film/{{Casablanca}}'', although this is a case where the guy could have the girl but gives her up.
* In ''Film/CastAway'', when Chuck returns, his girlfriend is already married to another man, since Chuck had been missing, presumed dead for several years. But the film ends with him meeting a possible love interest.
* There's a {{subver|tedTrope}}sion in the dance movie ''Centre Stage''. Peter Gallagher's character has married Ethan Stiefel's ex-girlfriend, and at one stage he snarks: "I got the girl." Later on, Stiefel wins over a rich, elderly woman who promises to fund his own dancing company and in doing so, allows him to leave Gallagher's theatre. He tells Gallagher: "I guess this time, ''I'' get the girl."
%%* ''Film/ChasingAmy'': Twice, even.
* Creator/CharlieChaplin's ''Film/TheCircus'' is an early film example.
* The budding romance between Salvatore and Elena in ''Film/CinemaParadiso'' is cut short by her disapproving parents and [[spoiler: the behest of Alfredo]]. At the end of the film, the two reunite in their late forties, and though they confess they are still in love, Elena cannot bring herself to leave her husband and daughter.
* ''Film/{{Clerks}}'' has Dante having trouble choosing between his current girlfriend Veronica or his ex Caitlin. Ultimately he realizes that Veronica is the one he loves, but thanks to Randall's interference she believes he loves Caitlin and breaks up with him. Although the ending implies he'll try to clear things up with her, related material and future films have made it clear they never got back together (or ''if'' they did, it didn't last). Ultimately averted in the sequel where he gets together with Becky Scott.
* The original ''Film/ConanTheBarbarian1982'' film has Conan gain wealth, vengeance, and the favor of a king... but in doing so he lost Valeria, his love. Even the epilogue, showing him as a king in the distant future, reveals he is still alone.
* ''Film/{{Daredevil|2003}}'': Due to Bullseye [[spoiler:killing the woman he loves]], Matt and Elektra don't end the film together. A deleted scene in [[Film/{{Elektra}} her spin-off]] shows she still loves him and wants to reunite, but by the end, she still doesn't go back to him.
* ''Film/TheDarkKnightTrilogy'':
** ''Film/BatmanBegins'', in which Rachel Dawes decides that Batman's commitment to Gotham won't allow him a fulfilling relationship with her. [[spoiler:This door slams shut for good when she is murdered in ''Film/TheDarkKnight''. However, before she was murdered she decides to leave Bruce, a fact he doesn't learn until ''Film/TheDarkKnightRises'' from Alfred.]]
** Later, in ''Film/TheDarkKnightRises'' he meets a new love interest, [[spoiler:who turns out to be the real antagonist of the film. The trope is finally averted when he gets together with [[DatingCatwoman Catwoman]]]].
* In ''Film/{{Darkman}}'', Peyton leaves Julie immediately after rescuing her. Not because he's disfigured (which she has faith he'll be able to fix), but because he's done so many terrible things for the sake of revenge that he now feels unworthy of her love or anyone's.
* ''Film/DontThinkTwice'': Although the couple were together at the beginning of the film, Sam breaks up with Jack at the climax, seemingly highlighting what his success has done to distance him from everyone. It's clear that this breakup has hit him the hardest, although they are all still friends at the end of the movie.
* ''Film/DrinkingBuddies'': Or rather, [[spoiler: Did Not Get The Guy. Luke still has Jill, but Kate, the female lead]] does not get either love interest.
* In ''Film/DumbAndDumber'', the "hero" doesn't get the girl, and kills her husband in a rage-filled IndulgentFantasySegue before leaving quietly.
* The original ending to ''Film/EuroTrip'', as a subversion of the standard formula for teen comedies; the writers eventually went with a more traditional ending.
* In ''Film/EveryWhichWayButLoose'', [[spoiler: Philo finally finds Lynn, but after discovering she's a hustler and having her slap him repeatedly, he simply walks away, leaving her crying on the ground]].
* In "Experiment in Terror" FBI agent ''Glenn Ford'' does not wind up with victim Lee Remick. They never have a moment, they do not have sex, there is nothing between them. This is the rare example of Truth In Television because it's his job and just being in a stressful situation together doesn't lead to two entirely different people who did not know each other before falling in love and living their lives together.
* Brian O'Connor seems to be on the receiving end of this trope in ''Film/TheFastAndTheFurious2001'' after learning that (a) his love interest Mia's brother is the crook he's after and (b) blowing his cover as an undercover cop. It gets resolved by ''Film/FastFive'' though.
* ''Film/AFewGoodMen''. Once the case is over, Creator/TomCruise and Creator/DemiMoore don't get together. They just leave. This aspect of the film could be considered a subversion of the typical movie conventions of protagonists always getting with the heroine regardless of their relationship working out in reality. In the case of this film, the pair were only brought together due to the legal case the plot follows. Though they had chemistry, it is noted that they have no grounds for a dedicated relationship once the trial is over.
* ''Film/FirstGirlILoved'': Anne loses Sasha by the end of the film, but at least she came to terms with her sexuality.
* The romantic comedy/road movie ''Forces of Nature'', where said forces seemingly conspire to make single mom Sandra Bullock and Ben Affleck a couple, but which ends with them going their separate ways.
* ''Film/FreeAndEasy'': Elmer's CannotSpitItOut problem leads to OneDialogueTwoConversations when he's telling his feelings to Elvira, leading her to think he's TheMatchmaker and accepting Larry's proposal instead. The film ends with Elmer brokenhearted.
* Scarlett O'Hara and Rhett Butler in ''Film/GoneWithTheWind''. Their last conversation with each other goes as follows:
--> '''Scarlett O'Hara:''' Rhett, if you go, where shall I go? What shall I do?\\
'''Rhett Butler:''' Frankly, my dear, [[PrecisionFStrike I don't give a damn]].
* ''Film/GoodBoys'': Max does get to kiss Brixlee, but their relationship is short-lived, they break up and he ends up with her friend. This didn't last too, as said friend breaks up with Max and Brixlee ends up dating her in turn. He does get Scout near the end, though.
* ''Film/TheGreenHornet'', refreshingly, has neither of the lead men getting with Creator/CameronDiaz's character despite repeated attempts to woo her, because (sensibly) she is not crazy about being treated like an object for them to use and fight over. Also the fact that he's a vigilante posing as a criminal.
* Because they are superheroes who weaken each other in proximity, ''Film/{{Hancock}}'' can't stay with his girl Mary. She's also married the next time he sees her. Of course, by this point, he has amnesia of who he is and didn't really care about it, even after he discovered the truth.
* ''Film/HappyTogether'': Boy in this case. While Ho and Lai are together at the start of the film, they break up roughly two-thirds into the movie and stay broken up by the end of it. Lai and Chang also don't get together.
* Unsurprisingly, it happens in ''Film/HesJustNotThatIntoYou''. Surprisingly, it's played straight, and out of the three relationships followed, only two of the three result in a relationship in the end.
* Creator/CharlesLaughton didn't get the girl in ''[[Film/TheHunchbackOfNotreDame1939 The Hunchback of Notre Dame]]'' (1939).
* In ''Film/IShotJesseJames'', Cynthy Waters leaves Robert Ford after she realizes she's more scared of Bob than in love with him. To rub salt in the wound, she dumps him for [[TheRival John Kelley]], throwing Bob into madness and [[DownerEnding leading to his death]].
* Franchise/IndianaJones gets the girl in each movie except ''Film/IndianaJonesAndTheLastCrusade''; though he would've liked it if his love interest, Elsa Schneider, hadn't lost her life. She finds herself in a LiteralCliffhanger, holding onto Indiana with one hand and reaching for the holy grail with the other. Indy can't persuade her to give up the prize and she falls to her death when her hand slips from its glove.
* ''Film/JamesBond'':
** ''Film/{{Skyfall}}'': The [[GirlOfTheWeek Bond Girl]] dies halfway in the movie. In fact, across all ''Bond'' movies, [[CartwrightCurse thirty percent of the girls die before the end of the movie]], and [[ChuckCunninghamSyndrome the rest are never seen again after the movie is over.]]
** Notably used in ''Film/QuantumOfSolace''.
** Parodied in a sketch on ''WesternAnimation/RobotChicken'' where they show that even when Bond ''gets'' the girl, he's terrible at ''keeping'' her because he keeps up with the same lame puns, dirty jokes, and then gets really clingy. The implication is that every Bond girl who didn't die ''dumped him'' immediately after the movie, which is why he's always single for the next one.
* In ''Film/JohnTuckerMustDie'', Kate changes her mind about humiliating the titular character but the other girls play the pre-recorded "I'm Dumping You" video. Defying genre convention, he doesn't take Kate back either and they remain as friends.
* ''Film/{{Ladybird}}'': The protagonist has two love interests, one of whom turns out to be gay, and one who turns out to be a total asshole who she angrily breaks up with after losing her virginity to. By the end of the movie, she's gotten over it though.
* In ''Film/LaLaLand'', Mia and Sebastian reunite five years after their break up, in which time Sebastian has achieved his dream of opening a jazz club and Mia has become a successful actress, married, and had a daughter. There's some awkwardness between them, but they both smile after they see that they have finally achieved their dreams.
* Happens in a [[DownerEnding majorly depressing]] way in ''The Last American Virgin''. It's unusual in that it was supposed to be a light teen comedy, but ends with the protagonist buying a gift for the girl that he thought loved him and going to a party to give it to her only to see [[spoiler:[[WhyWouldAnyoneTakeHimBack her making out with the jerk who dumped her after knocking her up]]. He angrily leaves the party without saying a word to either of them, and the last shot of the movie is him driving home alone through the night, [[TearJerker silently sobbing, heartbroken, and completely defeated]]]]. According to [[http://en.wikipedia.org/wiki/The_Last_American_Virgin#Plot_synopsis The Other Wiki]], this is the only film of the kind where it happens.
* In the second to final scene of ''Film/LittleManhattan'', Rosemary feels she's too young for a relationship and turns Gabe down. However, she acquiesces to dancing with him.
* ''Film/LoveActually'' - Part of the BittersweetEnding, [[spoiler:Sarah and Karl]] don't end up together. A lesser extent is with Mark. [[spoiler: He cares deeply for his friend Peter and was in love with Peter's girlfriend/wife Juliet for some time (to the point he even pushed her away out of loyalty for Peter and to save himself from the pain)]] but couldn't reconcile his feelings towards both because they were getting married. [[spoiler: Mark never expected to get Juliet from Peter and she gave him a pity kiss and they are able to get along as friends.]]
* ''Lucas'' - Though Lucas Bly tries desperately to win the heart of new girl Maggie (even joining the football team), she sees them as being [[BetterAsFriends better off]] [[JustFriends as friends]] and goes for Cappie Roew. Maggie even says, "We're JustFriends, Lucas," at one point.
* At the end of ''Film/{{The Maltese Falcon|1941}}'', Sam Spade turns in Brigid O'Shaughnessy for the murder of his partner.
* In ''Film/{{Marmoulak}}'', although Reza and Faezeh are attracted to each other, Reza does the honourable thing and urges her to go back to her reformed husband.
* ''Franchise/MarvelCinematicUniverse'':
** ''Film/{{Thor}}'' did not manage to end up with his love interest [[Characters/TheMightyThorSupportingCharacters Jane Foster]] since he destroyed the bridge that connects Earth to Asgard by the end of the film. They do reunite in ''Film/ThorTheDarkWorld'', but a scene in ''Film/ThorRagnarok'' has Thor pose for a selfie with a couple groupies and one of them mentions that Jane dumped him. He then tries to spin it as a "mutual dumping" to save face with Loki.
** ''Film/CaptainAmericaTheFirstAvenger''. In a great adaptation of a famous plotline from the comics, [[ComicBook/CaptainAmerica Steve Rogers]] [[spoiler: forces the Red Skull's flying wing down in the Arctic to save New York and other major U.S. cities]]. [[Characters/CaptainAmericaSupportingCharacters Peggy Carter]], Steve's comrade and love interest, has him promise to take her dancing the next week, with both knowing [[spoiler: he's all but guaranteed to die in the crash]]. Once [[spoiler: Steve awakens seventy years in the future,]] the realization must set in that [[spoiler:even if Peggy is still alive, and he somehow managed to find her again, she'd be an old woman of at least ninety, almost certainly with a family]].
--->'''Nick Fury''': ''(After just breaking the time issue to Steve)'' Are you going to be okay?\\
'''Steve''': Yeah. Yeah, I just... I had a date.
*** He gets to see her and say goodbye before she passes in the sequel, ''Film/CaptainAmericaTheWinterSoldier''. But then the trope pops up again: the entire movie hints at a potential romance between Steve and Natasha, the ComicBook/BlackWidow, even as she continuously suggests other women he should ask out. At the end, they end up developing trust and friendship instead of romance, and she tells him that he should give GirlNextDoor Sharon a call. Ultimately subverted in ''Film/AvengersEndgame''; [[spoiler: Steve is tasked with returning the stolen Infinity Stones to their rightful times to avoid throwing the future off balance, but decides to stay in the 50s and reunite with Peggy rather than return to the present. He's last seen as an old man PassingTheTorch to Sam as the next Captain America]].
** ''Film/TheIncredibleHulk'': Bruce Banner doesn't get to stay with [[Characters/MarvelComicsGammaMutates Betty Ross]], the woman he loves, because he's still a target of the military. To twist the knife further for poor Bruce, his second love interest (Black Widow/Natasha Romanov) dies collecting the Soul Stone from Vormir, and despite his best efforts, Bruce can't bring her back with the Infinity Gauntlet.
* J from ''Film/MenInBlackII'' mainly because the love interest is an alien princess and needs to return home to ensure the safety of Earth. This line sums it up.
-->'''Laura''': It's not fair.\\
'''Jay''': It never is.
* In ''Film/MyBestFriendsWedding'', the female lead Did Not Get The Guy.
* In the Italian comedy movie ''Notte Prima degli Esami'' ("Night Before the Exams"), LoserProtagonist Luca meets a girl named Claudia at a party and immediately falls for her. It was a brief meeting, and after the party, Luca doesn't know anything about her, except her name, and through the movie, he desperately tries to find out where she lives. Meanwhile, Claudia seems to return his feelings: we see her writing in her diary about "an amazing guy she met at a party". At the end (when they finally meet again), it turns out that Claudia was talking about one of Luca's friends, who was also at the party.
* ''Film/TheOldManAndTheGun'': In the end, Forrest Tucker can't enjoy his comfortable retirement with Jewell. At the age of 79, he robs four banks in one day and winds up back in prison for the final time.
* In ''Film/{{Once}}'' (as well as its ScreenToStageAdaptation), the developing romance between the two main characters remains unresolved, with both of them choosing to reunite with their respective exes. It's bittersweet, as while [[CannotSpitItOut the Guy and Girl clearly wanted to be with each other]], they at least left with a renewed faith in love.
* A rare female example in ''Film/ThePelicanBrief''. Creator/JuliaRoberts' character, who is the main character, and Creator/DenzelWashington's character were supposed to get together and were even scripted to have a lovemaking scene. However, UnfortunateImplications from the fan base of both actors caused the script to get rewritten where they part as close friends by the end of the film.
* Subverted in ''Film/{{Pixels}}'' - at first it seems like Lady Lisa is forever gone for Ludlow, but then she returns and they have BabiesEverAfter.
* Played for laughs at the end of the Creator/BobHope vehicle ''Film/ThePrincessAndThePirate'', where Hope's co-star from the various [[Film/RoadTo "Road To.."]] movies, Music/BingCrosby, cameos as the guy the film's heroine is actually in love with. This revelation of course provokes a sarcastic [[NoFourthWall fourth-wall-breaking]] rant from Hope.
* This is the CruelTwistEnding in ''Film/ThePurpleRoseOfCairo''. The heroine has to choose between Tom Baxter, a movie character who [[RefugeeFromTVLand literally walked off of a movie screen to be with her]], and Gil Shepard, the actor who played Tom Baxter in the movie. She chooses Gil, but [[FalseFriend he had only been pretending to be interested in her]]; all he cared about was saving his career by getting Tom to return to being a movie character. Once Tom returns to the movie for good, Gil takes a plane back to California without even saying goodbye.
%%* ''Film/TheRainmaker'': "So long, beautiful!" Averted in the book.
* In ''Film/RepoMen'', Remy winds up on a beach with his best friend Jake and his love interest, Beth, after his son publishes his book exposing all the dirty secrets about The Union, [[spoiler:except we find out he is in a neural net fantasy, Jake is still working to pay off the bill and Beth will probably be dead soon when The Union repossesses her [=ArtifOrgs=] for real]].
* ''Film/RequiemForADream'' ends with [[spoiler:Creator/JaredLeto's arm being amputated, Creator/JenniferConnelly prostituting herself for heroin, Tyrone in jail, and Jared Leto's mom in a mental institution. Jared Leto]], the main-est of the main characters, doesn't even bother asking the random Asian nurse to phone [[spoiler:Marion]], because he knows there's no way she's ever coming back. DownerEnding? Why yes, yes it is.
%%* ''Film/RomanHoliday'' in a particularly classy version of this trope.
* In ''Film/TheScorpionKing 2: Rise of a Warrior'', young Mathayus finally kills the BigBad ([[YouKilledMyFather his father's murderer]]) and ruins the plans of an evil goddess. As his {{love interest|s}} approaches him in a seductive manner, prepared to be his queen, he suddenly smiles and rides off into the sunset without her. So not only did he refuse the girl (with nothing in the film foreshadowing this) but he also refuses the crown. Would Akkad still fall (in the first film, Mathayus is the LastOfHisKind), if Mathayus stayed?
* In ''Film/ShakespeareInLove'', Shakespeare can't have his love because not only is he a common man, while she is a noblewoman, but he is married and she's engaged to someone else. His frustration over this leads him to change the ending of ''Theatre/RomeoAndJuliet''.
* In ''Film/SplendorInTheGrass'', where the male and the female leads are equally important characters, he ends up married to someone else.
* The reboot film ''Film/StarTrek2009'': Throughout the movie, Kirk constantly tries to get with Uhura, only for her to reject him every time. [[spoiler: It's revealed this is because she's already in an established, secret relationship with Spock. The expression on Jim's face when he realizes that his stoic First Officer got the girl instead of him is priceless.]]
* ''Film/StreetsOfFire''. Hero rescues his ex-girlfriend, but she stays with her current boyfriend. He rides away with his tough female sidekick, who insists that he's not her type.
* ''Film/SupermanReturns'' plays with this; Superman isn't ever going to wind up with Lois because she's engaged to Richard, but Richard will never see her fully commit to him either because she still loves Superman. The real 'fun' comes in when you realize that the only way that the situation will ever be resolved is by [[MurderTheHypotenuse eliminating a corner of the triangle]]. Then there's the little revelation that Superman is the biological father of Lois's son, Jason, yet the guy who Jason has seen as his father for his entire life has been Richard.
* In ''Film/TheTerminal'', Viktor, despite his huge effort and all the sweet things he tries, doesn't [[spoiler: end up with Amelia, who resumes her affair with the married official]]. Definitely [[BittersweetEnding a bit of a downer]], though quite a few reviewers later admitted that if she's like that, he's better off without her.
* ''Film/TheThirdMan,'' with its famous ending shot of the hero's love interest walking coldly past him without even a sidelong glance. The film pulled this off so well that its ending was lifted almost verbatim in both ''Film/TheDeparted'' and ''Film/MillersCrossing''.
* ''Film/TheTown'' - Doug is forced to flee Boston and can likely never return due to the FBI manhunt.
* In ''Film/{{Tron}}'', Flynn does not permanently hook up with either Lora, his former girlfriend (for whom he still has feelings) at the start of the film, or Yori, her program counterpart, although [[spoiler:he kisses the latter just before he leaves the electronic world, believing that he's about to die]].
* In ''Film/UpInTheAir'', Creator/GeorgeClooney's character did not get either girl.
* The BittersweetEnding in ''Film/VForVendetta'' has [[spoiler:V himself die in Evey's arms]] just as he confesses his love for her.
* ''Film/{{Vikingdom}}'': The hero Eirick is in a relationship with LoveGoddess Freyja before the start of the movie. When he is killed in combat, she manages to resurrect him on the condition that they can never be together again and he ends up living as a depressed hermit for the next decade. [[spoiler:When she convinces her old love to move on and hook up with his companion Brynna, she dies at the end of the movie, performing a HeroicSacrifice to save him. This means the dude lost his two separate love interests during the movie.]]
* ''Film/WhatACarveUp'': Ernie spends the film trying to impress Linda, but, at the end of the film, her previously unmentioned boyfriend (played by TeenIdol Adam Faith) arrives and takes her away, leaving Ernie heartbroken.
* Creator/WoodyHarrelson's protagonist from ''Film/WhiteMenCantJump''. He actually does start out with her as his girlfriend, and when she manages to become a champion on Jeopardy it seems they've [[EarnYourHappyEnding earned their happy ending]]. But she breaks it off with him when he (yet again) goes back to basketball hustling (to save his friend who had been robbed). They win the big game, but when he goes to win her back afterwards she's already ''gone'', having given up on him ever be done hustling for good.
* ''Film/WildWildWest'': The female lead reveals that Dr. Escobar is not her father, but her husband. Which she should have mentioned before. Although, the two male leads get something arguably more awesome: the bad guy's 80-foot SpiderTank!
* ''Film/TheWrestler'' has the main character choose the self-destructive life of wrestling rather than retire into obscurity with his new girlfriend. [[BolivianArmyEnding It's implied that he dies in the ring.]]
* Invoked straight in an early work of Creator/FrancisFordCoppola titled ''You're a Big Boy Now''. In this movie from [[TheSixties 1966]] Bernard, the protagonist, suffers this fate at the end, after spending all the movie chasing Barbara Darling. Actually, he doesn't get ''that'' girl...
[[/folder]]