As this is an Ending Trope, unmarked spoilers abound. Beware.
Times where the protagonist doesn't get together with whomever they've been pursuing in Literature.
- 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, but the death of the author means we'll never know.
- In the Albert Campion story Mystery Mile, Campion admires Biddy Paget and is upset when she chooses Marlowe Lobbett instead.
- Most of Jeremy's actions in Be More Chill, 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.
- 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.
- Charles Dickens gives this fate to Scrooge in A Christmas Carol; 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.
- Clockpunk and the Vitalizer: Clockpunk doesn't get with the Vitalizer. It's probably for the best since she's a superhero and he a supervillain. He shows her some respect before fleeing, however.
- Daisy Miller is not a sad book because the girl dies, but because the guy doesn't realize her worth while she's alive.
- In the Deptford Mice trilogy by Robin Jarvis, 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 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.
- Terry Pratchett's Discworld: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.
- Jim Butcher's The Dresden Files: Harry Dresden. He's had four Love Interests in 14 books, and it hasn't worked out with any of them. 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. 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 The 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 a 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. 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 Mab, the Winter Queen of Faerie, Queen of Air and Darkness. But nothing good is coming out of that.
- E. T. A. Hoffmann:
- In The Artushof 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 The Entail 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 The Sandman (1816) 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 Farseer Trilogy is possibly one of the most depressing examples. Remedied at the end of the Tawny Man trilogy, in which Fitz Chivalry 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 Earn Your Happy Ending.
- Both of the books in Marti Steussy's "First-In" duology have bittersweet gender-flipped examples. In Forest of the Night, Gaylord Hess spurs the conflict between humanity and the 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, Aage is simply too reluctant to compromise on the dilemma regarding the world's Mirror Chemistry, leading Disa to ultimately distance herself from him. Forest leaves Gaylord's and Hashti's romantic futures ambiguous; the Distant Finale of Dreams gives both Disa and Aage Second Loves: another young First-In member for Disa, and the sweet local girl Gretchen for Aaage.
- The First Law:
- 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 Anguished Declaration of Love, and is Happily Married 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 Gorky Park. Arkady Renko tells damaged love interest Irina Asanova to stay in America while he'll return to Cold 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.
- 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.
- 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 Harry Potter and the Deathly Hallows.
- 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.
- Hollow Places 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.
- Eragon from the Inheritance Cycle. By the end of the series, he decides to leave Alagaesia forever to raise a new generation of dragon riders, while Arya remains in the continent to take on the mantle of the Queen of Elves.
- 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.
- Happens in Ian Fleming's James Bond novels more regularly than the films would have you believe. (In the very first novel, the love interest commits suicide, in Moonraker she's engaged to another man, in On Her Majesty's Secret Service his wife is murdered at the end, and in From Russia with Love Bond is poisoned before any consummation can occur).
- 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 his beloved Sue decides to go back to Philloston after the big tragedy.
- Hans Christian Andersen's "The Little Mermaid" does not get her Prince, though in every way she deserves it. 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 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. - Little Women: The One Guy Laurie does not get the member of the starring Four-Girl Ensemble he originally wanted, who is also the one both the original and the modern fanbase wanted him to get. It's not like there isn't a Fritz/Jo fandom or their Umbrella of Togetherness scene isn't the very essence of sweet and romantic. Laurie/Amy, on the other hand...
- 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.
- 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.
- Freida in Only Ever Yours 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 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 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.
- Kim Stanley Robinson's Pacific Edge. Kevin Claiborne does not get Ramona; instead, she goes back to her Jerkass boyfriend, Alfredo.
- Anthony Hope's The Prisoner of Zenda. The girl is expected to marry the actual king instead of his decoy double (with whom she's fallen in love).
- The Reynard Cycle: Reynard the Fox ends heavily on this note, and it gets worse with every new installment.
- 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).
- A Song of Ice and Fire: If one goes with the theory 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.
- The Starchild Trilogy: In Rogue Star, Andy Quamodian spends most of the book trying to rescue Molly Zaldiver who he's always been in love with, but in the end, the only way she can survive is to merge with the living star Almalik.
- In Poul Anderson's "Starfog", Laure does not get Graydal. The Jaccavrie AI explains it's impossible: they aren't interfertile, and her kind have developed a compulsive need to reproduce.
- Tailchaser's Song: 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, it's heavily implied she's spayed). Eventually this gets to be too much and Tailchaser leaves Hushpad and her owners.
- 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.
- Isaac Asimov's "True Love": The surprising Plot Twist at the end has Milton end up going to jail while Joe gets the girl.
- Adam and Nina's repeated failures to get married drive much of the plot of Vile Bodies. 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 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.
- Exaggerated Trope in La Vita Nuova; 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 The Wainscott Weasel, the title weasel does not get his love interest (a striped bass named Bridget) due to the humans cutting out the pond.
- Warrior Cats: Ashfur did not get 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 Wuthering Heights Heathcliff does not get Catherine. In fact, he marries her sister-in-law Isabella.
- Dean Koontz's novel Your Heart Belongs to Me ends like this, which is something of a break in formula for him.
