A rare case where The Protagonist— who is clearly not celibate — doesn't end up with the romantic female lead. Someone else wins her heart or she has no choice but to marry someone to save her family or something. For whatever reason the hero ends the story alone. It can be played either for comedy or tragedy. It isn't always a Downer Ending, but it sure does tend to be that way.
Despite the name, this trope can just as easily apply to not getting the guy.
Subtrope of No Romantic Resolution. Compare to Better as Friends and Romantic Runner-Up. Contrast Everything but the Girl, where the protagonist usually does get the girl eventually. Not to be confused with two leads not ending up together because one of them dies — that is a different trope, and Platonic Life Partners where neither of them wanted each other in the first place. See also Dump Them All, where the protagonist rejects all of his Love Interests instead of them leaving him.
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Anime and Manga
A running gag for Sanji in One Piece. For a womanizer, no single woman was ever seen falling for him. Zoro and Kuina is straighter example. Life was unkind to the guy.
Despite having three potential Love Interests, the main character of FLCL ends up with no one. It implies that he will end up with Ninamori but only after they're not kids anymore and are more mature. This is averted in the manga, where he ends up with Haruko but he has to chase after her.
Yamcha gets a hardcore case of this in the Cell Saga of Dragon Ball Z. Bulma, whom he spent more than half of his life after, ends up with Vegeta. While he continues dating other women, he never married which had been his dream.
Inevitable in nearly all installments of Weiß Kreuz due to the protagonists being Doom Magnets - the few potential love interests who don't end up dead get the It's Not You, It's My Enemies treatment. The only exception here is Farfarello, who leaves with his love interest in the end of the Schwarz audio drama to lead a happy, kill-free life.
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 dramatically cut down from its planned run, that was the intended ending all along.
Kamina dies shortly after he and Yoko admit their feelings towards each other.
Kittan 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 Lotus-Eater Machine one of her alternate/happier lives has her marrying him.
Simon and Nia get married, but immediately afterward, she fades away due to an earlier Heroic Sacrifice.
In The Girl Who Leapt Through Time, 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:
Chiaki: I'll be waiting in the future. Makoto: I'll be right there. I'll run there.
In the SlayersLight Novel series, the bounty hunter Luke constantly tries to win the affections of his perpetually grumpy partner Millina, all to no avail. This ultimately comes to a climax in the fourteenth novel when 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.
Princess Tutu: Ahiru does not get the boy, but gets to stay with Fakir as a duck.
Welcome to the NHK: though they stay friends. At least in most versions. The anime and novel both end fairly ambiguously, but the manga has Satou promise to rekindle their relationship after he cleans up.
Hazuki from Yami to Boushi to Hon no Tabibito 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 fans.
This trope has been displayed between Jiraiya and Tsunade. Even in his final moments, Jiraiya reflects that he failed in winning Tsunade's affection. Making this even worse, Tsunade implies that she was going to confess to him when he returned.
Also, Sakura Haruno and Sasuke Uchiha, thanks to the latter's Face-Heel Turn. However, it has not been completely ruled out, since Sasuke returns to fight in the Fourth Great Shinobi War and declares that he will become Hokage.
Fantastic Children fits this perfectly and its even a large part of the plot. He seems to eventually accepts to live with it. The guy she picks is a good guy and all, but it is still a bit of a downer.
School Rumble. 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. 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.
This is played straight in the third act of 5 Centimeters per Second, despite a good taunting/glimmer of hope thrown in for good measure at the end - which doesn't pan out.
In Pokémon Special, 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.)
Likewise with Meowth in the in the Pokémon 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.
The final chapter of Ciguatera reveals that protagonist Ogino eventually broke up with 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 they're both shown to be happy.
Code Geass had a field day with this trope; Shirley died shortly after her Anguished Declaration of Love so she and Lelouch didn't end up together. Season 2 also spent a lot of episodes teasing the sexual tension between Lelouch and Kallen. That also came a 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. And, given the subtext, Lelouch did not get Euphie either.
The manga ending for ×××HOLiC follows much in the same vein. Set in a Distant Finale 100 years in the future where Watanuki has lost both Himawari andDoumeki to them dying of old age. Made even sadder by the fact that after Tsubasa ended Watanuki couldn't leave his Inn Between the Worlds 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 accepts it though, congratulating her on her marriage.
Played with Onani Master Kurosawa. Kurosawa starts an unholy alliance with Kitahara, which later stars 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 on 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 gets over Takagawa, who seems quite happy with Nagaoka, and ends dating Sugawa, the yankee that beat his ass because he came over her uniform to avenge Kitahara.
Gender-inverted examples are common in the Macross series:
A similar fate happens to Ranka Lee in the second Movie of Macross Frontier, 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 Alternate Continuity, this is averted in the TV series.
The 2003 anime version of Fullmetal Alchemist ends this way (twice): in the TV ending, Ed is trapped in our world searching for a way to get back while Winry and Rose are left behind, and in The Movieafter 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.
No. 6: Shion Did Not Get The Guy Or Girl: Not only does Nezumi leave him behind when they're done, but Safu, his Het Option, Ascends to a Higher Plane of Existence. However, there might be hope because Shion promises that he'll meet Nezumi again at the end of the anime and novels.
Patlabor: No matter the continuity, Gotoh never ends up with his fellow captain, Shinobu.
In Jewelpet Sunshine, the protagonist Kanon dates her crush Mikage for several episodes. Then comes The Reveal that they're siblings, and Kanon has to forcibly give him up, without a consolation prize.
In Princess Mononoke, 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.
Yorick in Y: The Last Man, in two different ways. 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 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 (who became pregnant with his child early on), and in the Distant Finale, the daughter explains that they had a troubled relationship, because Yorick never stopped carrying a torch for 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.
In the 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. Don Rosa 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.
Empire State: 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 Maybe Ever After ending.
For all the troubles Weakling Smurf went through in The Smurfs comic book story "The Olympic Smurfs", he winds up not getting Smurfette (or at least, not getting a kiss from Smurfette) by the story's end.
Played with in a very gruesome way in Les Légendaires during the Anathos Cycle. As the protagonists prepare to fight the God of Evil Anathos, Danael, feeling tired with everything that happened so far, eventually fully confess his feeling to Jadina once and for all, and proposes her to marry after the fight. She agrees and they share a kiss... then after the fight, Anathos ends up taking over Danael's body. And 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 The Hero.
As a young man, Superman never married his college love Lori Lemaris, who turned down his proposal and finally married someone else. Of course, Supes eventually fell in love with Lois Lane and even managed to stay friends with Lori, so it all worked out okay.
King City: 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, after helping Anna rescue Max, Joe accepts that she's not his girl anymore. It looks like they'll remain friends.
In The Masks We Wear, Zuko loses his affection for Mai as a result of his increasing similarity to his sister.
In Shatterheart Fai had been struggling 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.
At the end of Disney's Pocahontas, John Smith, severely injured, returns to Europe, leaving Pocahontas behind. Possibly the only truth in television moment in the entire movie, acknowledging that, no, Pocahontas and John Smith did not end up together. This carries over into the sequel, when John Smith still loves Pocahontas, but she hooks up with John Rolfe.
Toy Story 3: Although Buzz Lightyear and Jessie, and to a much lesser extent, Mr. and Mrs. Potato Head and Barbie and Ken are now finally united with each other, Woody and Bo Peep, unfortunately aren't. (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, and you can see how down Woody is because of that.)
The Rankin/Bass ProductionsJack Frost special follows the titular sprite as he tries to gain the things he needs to become human: a house, a horse, a bag of gold, and a wife. He set his sights on the one girl who loved Jack Frost, the sprite... but he couldn't get her to love him as Jack Snip, the human. In the end he returns to being a sprite and she marries someone else.
Requiem for a Dream ends with Jared Leto's arm being amputated, Jennifer Connelly prostituting herself for heroin, their Black Best Friend 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 Marion, because he knows there's no way she's ever coming back. Downer Ending? Why yes, yes it is.
Annie Hall ends with the main characters breaking up.
Toward the end of Harold Ramis' remake of Bedazzled, 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 his final wish, that 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.
Batman Begins, in which Rachel Dawes decides that Batman's commitment to Gotham won't allow him a fulfilling relationship with her. This door slams shut for good when she is murdered in The Dark Knight. However, before she was murdered she decides to leave Bruce, a fact he doesn't learn until The Dark Knight Rises from Alfred.
Later, in The Dark Knight Rises he meets a new love interest, who turns out to be the real antagonist of the film. The trope is finally averted when he gets together with Catwoman.
In Tim Burton's Batman Returns, 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!
The original ending to Euro Trip, as a subversion of the standard formula for teen comedies; the writers eventually went with a more traditional ending.
Unsurprisingly, it happens in He's Just Not That Into You. Surprisingly, it's played straight, and out of the three relationships followed, only two of the three result in a relationship in the end.
In Every Which Way But Loose, 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.
A Few Good Men. Once the case is over, Tom Cruise and Demi Moore 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.
Parodied in a sketch on Robot Chicken 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 Shakespeare in Love, 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 engaged to someone else. His frustration over this leads him to change the ending of Romeo and Juliet.
Streets of Fire. 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.
Superman Returns 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 eliminating a corner of the triangle. And 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.
The Third Man, 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 The Departed and Miller's Crossing.
In The Terminal, Viktor, despite his huge effort and all the sweet things he tried, did not end up with Amelia, who ended up resuming her affair with the married official. Definitely was a bit of a downer, though quite a few reviewers later admitted that if she's like that, he's better off without her.
In 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.
In Up in the Air, George Clooney's character did not get either girl.
Love Actually - Part of the Bittersweet Ending, Sarah and Karl don't end up together. A lesser extent is with Mark. 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. It arguably ends well as Mark never expected to get Juliet from Peter and she gave him a pity kiss and they are able to get along as friends.
The original Conan The Barbarian 1981 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.
In Cast Away, 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.
J from Men In Black 2 mainly cause the love interest is an alien princess and needs to return home to ensure the safety of Earth. This line pretty much sums it up.
Laura: It's not fair. Jay: It never is.
The protagonist from White Men Cant Jump. He actually does start out with her as his girlfriend. But she leaves him to start fresh and manages to becomes a champion on Jeopardy. He goes on to win her back. But is pulled back into basketball hustling to save his friend who had been robbed. They win the game but she leaves him without saying goodbye, the irony to this was that it was meant to be his last game.
The Wrestler has the main character choose the self-destructive life of wrestling rather than retire into obscurity with his new girlfriend. It's implied that he dies in the ring.
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.
An unusual version is done in The Brothers Grimm - both of the brothers love Angelika and both 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 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 he kisses the latter just before he leaves the electronic world, believing that he's about to die.
The Green Hornet, refreshingly, has neither of the lead men get with Cameron Diaz'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.
At the end of The Maltese Falcon, Sam Spade turns in Brigid O'Shaughnessy for the murder of his partner.
There's a subversion 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, allow him to leave Gallagher's theatre. He tells Gallagher: "I guess this time, I get the girl."
Wild Wild West - the female lead reveals that Dr. Escobar is not her father, but her husband. Which she should have mentioned before.
The Town - Doug is forced to flee Boston and can likely never return due to the FBI manhunt.
Lucas - Though Lucas Bly tries desperately to win the heart of new girl Maggie (even joining the football team), she sees them as being better offas friends and goes for Cappie Roew. Maggie even says, "We're Just Friends, Lucas," at one point.
In Brick Brendan's first love interest dies at the beginning, and his second turns out to have orchestrated her murder.
Thor did not manage to end up with his love interest Jane since he destroyed the bridge that connects Earth to Asgard by the end of the film.
Captain America: The First Avenger. In a great adaptation of a famous plotline from the comics, Steve Rogers forces the Red Skull's flying wing down in the Arctic to save New York and other major U.S. cities. Peggy Carter, Steve's comrade and love interest, has him promise to take her dancing the next week, with both knowing he's all but guaranteed to die in the crash. Once Steve awakens seventy years in the future, the realization must set in that 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, Winter Soldier. But then the trope pops up again: the entire movie hints at a potential romance between Steve and Natasha, the Black Widow, 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 Girl Next Door Sharon a call.
Invoked straight in an early work of Francis Ford Coppola titled You're a Big Boy Now. In this movie from 1966 Bernard, the protagonist, suffer this fate at the end, after spending all the movie chasing Barbara Darling. Actually, he doesn't get that girl...
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.
In The Scorpion King 2: Rise of a Warrior, young Mathayus finally kills the Big Bad (his father's murderer) and ruins the plans of an evil goddess. As his Love Interest 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 Last of His Kind), if Mathayus stayed?
In John Tucker Must Die, 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.
In Splendor in the Grass, where the male and the female leads are equally important characters, he ends up married to someone else.
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 pretty much 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 protagonist of Adam doesn't end up with his love interest.
Scarlett O'Hara and Rhett Butler in Gone with the Wind. 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, I don't give a damn.
Because they are superheros who weaken each other in proximity, Hancock can't stay with his girl Mary. She's also married the next time he's 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.
Brian O'Connor seems to be on the receiving end of this trope in The Fast and the Furious 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 the fifth film though.
Indiana Jones gets the girl in each movie except Indiana Jones and the Last Crusade; though he liked would've if his love interest, Elsa Schneider, hadn't lost her life. She found herself in a Literal Cliffhanger, holding onto Indiana with one hand and reaching for the holy grail with the other. Indy couldn't persuade her to give up the prize and she fell to her death when her hand slipped from its glove.
In Repo Men, 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, 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.
A rare female example in The Pelican Brief. Julia Roberts character, who is the main character, and Denzel Washington's character was suppose to get together and was even scripted to have a lovemaking scene. However, Unfortunate Implications 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.
The reboot film Star Trek: Throughout the movie Kirk constantly tries to get with Uhura, only for her to reject him every time. 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.
The budding romance between Salvatore and Elena in Cinema Paradiso is cut short by her disapproving parents and 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.
In the second to final scene of Little Manhattan, Rosemary feels she's too young for a relationship and turns Gabe down. However, she acquiesces to dancing with him.
Quasimodo:(to a statue, sobbing) Why was I not made of stone like thee?
Despite all of the eponymous character's attempts to win the girl in The Great Gatsby, she stays with her husband. Gatsby takes a lie for her that gets him killed.
Kelson falls deeply in love with Rothana Nur Hallaj, a 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 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.
Severus Snape did not get the girl, the girl being Lily Potter nee Evans, before the events of the Harry Potter series, as revealed in the 7th book.
Adrian Mole 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.
Elaine (who shows up later in the books than Susan, but who 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. Literally; Susan's love for Harry protects him from the White Court. Unfortunately, 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, Harry ends up killing her to trigger a bloodline curse that kills all of the Red Court vampires in the world. Ouch....
Shiela, a girl working at an occult bookstore with perfect memory recall, seems like a good possibility in Dead Beat. Turns out she's just a psychic projection/mental clone created by the Fallen Angel residing in Harry's head. He does actually manage to redeem the demonic entity, right before she kills herself to save his life. Although Word of God is that Lash showed up in Ghost Story... somewhere, as did Lasciel.
Anastasia Luccio, fellow wizard born three centuries ago, who got dumped in a pretty young girl's body via magic and developed a budding relationship with Harry. 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 Unresolved Sexual Tension at the end of Changes, but then Harry catches a bad case of sniper. In Cold Days, Karrin and Harry finally have a Big Damn Kiss, but she has very good reasons to hesitate, such as Harry gets a hard-on during the Big Damn Battle, thanks to the Winter Knight's Mantle and an arguably better potential match for Harry in Molly who is now 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* 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.
Harry did manage to bed Mab, the Winter Queen of Faerie, Queen of Air and Darkness. But nothing good is coming out of that.
Hans Christian Andersen's "The Little Mermaid" did not get her Prince though in every way she deserved to. Here, too, the film adaptation changed this (and even added 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, "The Swineherd", does not get the prince because she cared more about the musical toy that he created than she did about him. Unlike the little mermaid, this princess did not deserve the prince at all - she was too materialistic to love him for who he was.
The ending of the classic Robert Munsch children's tale The Paper Bag Princess 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.
In 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.
In his non-Discworld novel Nation Mau and Daphne do not end up together due to duties and obligations to their respective cultures, though it's implied they are reincarnated as paired dolphins after their deaths.
His Dark Materials: 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 Tear Jerker depends on the reader.
Daisy Miller is not a sad book because the girl dies but because the guy doesn't realize her worth while she's alive.
The First Law plays this 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.
Dean Koontz's novel Your Heart Belongs to Me ends like this, which is something of a break in formula for him.
Thomas Hardy's Jude the Obscure. 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.
In Wuthering Heights Heathcliff does not get Catherine. In fact, he marries her sister-in-law Isabella.
Kim Stanley Robinson's Pacific Edge. Kevin Claiborne does not get Ramona; instead, she goes back to her Jerkass boyfriend, Alfredo.
Martin Cruz Smith's Gorky Park. Arkady Renko tells damaged love interestIrina Asanova to stay in America while he'll return toCold War era Russia. It was her dream to escape the Soviet Union, and Renko doesn't find America to be any better than the USSR.
Book of the New Sun: Severian's first love, Thecla ends up killing herself to avoid the torture and his amnesiac second love, Dorcas leaves him when she finds out that she is his grandmother. It should be noted that although Thecla dies, Severian's persona is merged with hers through a sort of cannibalistic Eucharist.
If one goes with the theory in A Song of Ice and Fire that Petyr 'Littlefinger' Baelish is what would happen if a stereotypical fantasy hero was plonked into a Crapsack World, then this is the reason why he's so screwed up and why Westeros is now even more of a Crapsack World.
Circe and Calypso in The Odyssey - 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.
Eragon from the Inheritance Cycle. Never mind that 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 Forever Alone has a patron saint, it's this guy.
This is what kickstarts the philosophizing in Repetition.
Robin Hobb’s Farseer Trilogy is possibly one of the most depressing examples. Remedied at the end of the Tawny Man trilogy, in which Fitz Chivalryfinally 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 Earn Your Happy Ending.
Occasionally happens in the Jack Reacher novels. Die Trying is an example; while Reacher and the female lead have a mutual attraction and once engage in Glad-to-Be-Alive Sex, she is in love with someone else and moves in with (and possibly marries) him at the end of the novel.
A Foregone Conclusion of Saving Charlie, as anyone who's seen the episodes of Heroes that it's based upon knows that Hiro doesn't manage to save Charlie (though 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).
In Poul Anderson's Technic History 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.
Live Action TV
The Wonder Years ends with a closing epilogue revealing that, after six seasons, Kevin and Winnie part ways and he ends up marrying someone else.
In the BBC version of Casanova, the titular character tragically did not get the girl. The Hollywood version cheapens the story with a tacked-on happy ending.
Brian Kinney at the end of the US version of Queer as Folk. 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, the couple split up so that Justin could pursue an art career in NYC.
Shua in Sky Blue manages to bring down Ecoban, but thanks to Locke, it's almost certain Jay will die.
Tony and Michelle in Skins end up going their separate ways because of different universities.
Lee "Apollo" Adama on the new Battlestar Galactica is practically the patron saint of this trope. He blows it with at least four women over the course of the show: Kara "Starbuck" Thrace, his 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 Dogged Nice Guy 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. And Shevon, a prostitute he frequents for all of one episode and Replacement Goldfish for Gianne, who pushes him away because, well, she's a prostitute.
Played for laughs with Simon Cooper in The Inbetweeners. 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.
Kamen Rider Double hinted in early episodes that Shotaro would eventually get together with Akiko, only for her to end up with Terui instead.
The Doctor occasionally does this on Doctor Who, although mostly in the Revival. He didn't get together with Rose due to a combination of Cannot Spit It Out 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 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 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 doppleganger 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 Implied Love Interest for the Fourth Doctor. Despite plenty of UST, nothing happened whatsoever and he eventually abandoned her several hundred miles away from where she was actually from and 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 Mayfly-December Romance factor and because he's bad at handling goodbyes. He then finally tells her with his new face, "I Love You, Sarah Jane", before leaving her again.
Lancelot from Merlin. In this version, Arthur/Guinevere is not a political marriage, but a real love connection. Also Merlin and Freya.
And Guinevere doesn't get the guy, with Arthur dying at the end.
iCarly: Carly Shay doesn't get the guy at the end of "iOMG", but since this is a season finale cliffhanger, the next season could resolve it differently. Resolved (for now at least) and subverted. Sam doesn't end up with Freddie either.
Though in the end, Carly does get the guy right before she leaves.
A.N.T. Farm: Chyna showed signs of this ala 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 due that Fletcher stays in New York, but even then, Chyna still never gets a chance to love Fletcher.
Hikari Sentai Maskman: Takeru does not end up with Iyal because she is now the queen of Tube and 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."
Engine Sentai Go-onger showed that Sosuke and Miu had feelings for each other; but ultimately nothing comes of it and they return to their respective lives.
GekiRed, HurricaneRed and GoseiRed all have movie-only love interests that don't re-appear for the TV series, thus they do not get the girl.
Degrassi has JT's Abhorrent Admirer 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).
Sweet Charity. Although all signs point to the contrary, Oscar winds up leaving Charity.
On a more comical note, 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 Tear Jerker 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.
Peter Ustinov'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, tick, tick... BOOM!, 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 Just Friends, and for his birthday she gives him sheets of blank paper with which to write to her.
In Street Scene, 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.
The ending to Metal Gear Solid shows Snake and Meryl riding off together into the sunset. Cue the fourth game where Snake's an old man and Meryl gets married to the very guard she knocked out at the beginning of the first game. (See Cartwright Curse.) 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. See also Ellen Madnar and Holly White from the first two games.
Full Throttle 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.
While the ending of Persona 2: Innocent Sin is an example of that other trope, Eternal Punishment plays this straight as 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 with Maya accepting this and walking by Tatsuya without saying anything is a real Tear Jerker.
In fact this is built into the title of the games; this is Tatsuya's "Eternal Punishment" for the "Innocent Sin" that he commented during the first game.
In Fire Emblem 7, 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 swordsmen, 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.
In the same title, Harken and Vaida must part ways due to their dedication to their respective lords.
Ike and Elincia in Fire Emblem: Path of Radiance, despite a decent amount of Ship Tease between them. By the sequel, the chemistry between them is nonexistent and Elincia's feelings have shifted towards Geoffrey (and possibly his sister Lucia).
Most of the origin stories in Dragon Age: Origins include an extra one-sided-or-not Love Interest, 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 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 and their child.
Dragon Age II reveals this to be the fate of a Warden who romanced Leliana or Zevran, as the Warden seems to have vanished.
Dragon Age II has this occur repeatedly. Notably 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. Similarly, if a female Hawke romances Sebastian, but sides with the Mages and refuses to kill Anders, he breaks up with Hawke and leaves to raise an army to wage war on Kirkwall.
Neverwinter Nights: Hordes of the Underdark reveals that the Hero of Neverwinter was good, male, and completed the romance subquest with Aribeth. And then 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 The Bastard Of Kosigan has the hero's former Love Interest die an unavoidable death at the hands of French assassins, even if you attempt to renew your relationship with her.
Knights of the Old Republic and the sequel has both Revan and 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 Revan that 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).
The Prince of Persia (2008): Epilogue ends on this note. After an entire game's worth of semi-witty Will They or Won't They? sexual tension, Elika finally has enough and literally runs off on the Prince because he freed the 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. Nice Job Breaking It, Dumbass.
Adol in the Ys series, almost every time. Of course, apart from Feena in I/II, it was more like the various girls Did Not Get The Guy.
Soul series: According to the Soulcalibur V profile for Leixia (daughter of Xianghua), her father is not Kilik, her Love Interest for the previous four games.
Somewhat subverted in that Kilik and Xianghua were together for a period of time; Kilik left because he realized they couldn't truly be together and thus vowed to protect Xianghua and the world she lived in as thanks for her selfless, unconditional love for him. However, he did consummate his relationship with Xianghua before departing for good, which led to Xianghua's firstborn: Xiba. In Kilik's case, it's "Did Not Keep The Girl" (or perhaps "Could Not Keep The Girl").
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 Honorary Uncle's luck.
Shadow Hearts does this a few times. The Canonical ending of the first ends with Alice dying, meaning Yuri did not get the girl after all. However, Yuri's next apparent love interest, Karin, Was sent into the past, meaning she did not get the guy....instead becoming his mother. But, the Stable Time Loop allows Yuri to earn his happy ending after all.
Final Fantasy X: At the very end, Yuna doesn't get the guy; he never existed in the first place, technically.
Fate/stay night's Fate route: In the most tearjerking way, Shirou doesn't get to keep Saber, and life moves on. However, in Realta Nua's bonus ending of Fate they 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 Shirou kills Sakura, Shirou destroys his remaining humanity to pursue Kiritsugu's dream; if Rin kills Sakura, Shirou is driven to despair due to previously surrendering his dream to protect Sakura.
The Phoenix Requiem ended with 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.
In Katamari (a comic based on Katamari Damacy) had a story arc revolve around the Prince of Cosmos helping a man try to regain his girlfriend by rolling up a katamari of all the thing she likes as a show of affection. However when presented it to, she shows she flattered by the gesture but let's him down gently that she isn't interested in pursuing the relationship.
Red vs. Blue. 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. Too bad he thought she was killed by the Meta and he was killed before she was revealed to still be alive.
Batman Beyond: Throughout the DCAU, Bruce Wayne has had many love interests: Catwoman/Selina Kyle, Zatanna (one-sided only, Bruce always considered them Just Friends), Talia Al'Ghul, Andrea Beaumont, Wonder Woman, Barbara Gordon/Batgirl... He doesn't end up with any of them and ends up a single, old man.
He also made-out with the Cheetah in a particularly memorable scene.
Peter in The Spectacular Spider-Man, due to premature cancellation. The season two finale ends with Gwen remaining with Harry out of pity.
Also lampshaded in Spider-Man: The Animated Series 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 Teen Titans. With Beast Boy: first Terra had a Face-Heel Turn; then a Heel-Face Turn that resulted in her being 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 Teen Titans Go! tie-in comics, however, 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."
A gender reversed version happens in Family Guy 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.
Played for Drama in Thundercats 2011 when Rebel Prince and royal heir Lion-O develops a crush on Cheetara, a woman he discovers is a member of his Church MilitantPraetorian Guard, he realizes his Lancer brother Tygra, also has feelings for her. As they set off on a shared journey, the two develop a passive-aggressive, increasingly toxic Sibling Triangle rivalry for her affections to which she remains largely 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 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 fortelling Tygra's betrayal.
Scooby-Doo! Mystery Incorporated: Shaggy and Velma have hooked up prior to the series' beginning, 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), but in the Grand Finale's new timeline, they are Happily Married.
6Teen: Judd with Starr when the latter decided to go goth.
Regular Show: Mordecai's budding relationship with Margaret is cut short by her leaving town after being accepted into her dream college.