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- CLANNAD: The Official Couple of Tomoya and Nagisa has them eventually getting married and expecting a child. Death By Child Birth separates the couple leaving their child Ushio with a broken father and no mother.
- Tuxedo Mask and the eponymous Sailor Moon. After they're reincarnated, he almost dies, she has to fight against him when he's evil and brainwashed, he's taken away from her many times, and so on. But they are always together.
- In Ten Yori Mo, Hoshi Yori Mo, a good part of Mio and Rei/Shou's conflict of their relationship deals with this. They went through this twice in different centuries. In both centuries, it ended up badly for them.
- Natsuki and Masaki from Amakusa 1637 were already together when the story started. A good part of their ordeals is less about getting together and much more about staying together.
- Poor Miaka and Tamahome in Fushigi Yuugi get hit with this quite a bit, especially in the first series. Kidnapping, Brainwashing, Attempted Rape, Poor Communication Kills resulting in a few breakups, obstructive stalkers and near-death experiences made these two earn their Happily Ever After.
- Kaoru and Aoi in Ai Yori Aoshi. They're both head over heels for each other, the problem is that Aoi's family doesn't approve (to the point of trying to physically force her to marry another man) and that several of their associates are beautiful young women who aren't aware of Kaoru's feelings for Aoi and are interested in Kaoru themselves.
- Guts and Casca from Berserk are very much that Darker and Edgier version. From their first meeting, the story was set on bringing these two together, and their beginning relationship was rough enough as it was. When they did admit their feelings to each other and become official, the universe made it its official mission to keep the two apart by any means necessary.
- Habaek and Soah from The Bride Of The Water God. Anytime it seems their relationship is going farther, the universe brings some more problems to them; either of trust, with other gods or some Love Triangle.
- In Beyond the Boundary, Akihito and Mirai get hit with this hard. Akihito is a half-human, half-youmu hybrid. Mirai is from a spirit hunter clan whose blood is deadly to youmu. Even worse, it's revealed that Mirai was given a mission to assassinate Akihito because the youmu inside him, known as Beyond the Boundary, is a powerful reality warper who could potentially destroy the world. Mirai can't bring herself to do it because she realized Akihito was the only one who understood her and cared for her, and that she'd fallen in love with him. So rather than kill Akihito, Mirai sacrifices herself and absorbs Beyond the Boundary, essentially wiping herself from existence.
- Taken Up to Eleven in the movie, Beyond the Boundary: I'll Be Here. Akihito falls into depression after Beyond the Boundary brings Mirai back to life at the cost of her losing her memories. He constantly tries to avoid her and has a pained expression whenever he sees her, unable to accept that she's forgotten about him and all they went through together. When Mirai confronts him about this, he insists that he just happened to pass by when she regained consciousness on the roof, and that the reason he broke down in tears upon seeing her was because of his glasses fetish. Despite all of his friends telling Akihito to tell Mirai the truth, he stubbornly refuses because he feels he'd be robbing her of living a normal life. And when Mirai starts to regain her memories after visiting a park she and Akihito had gone to in the past, Akihito tells her that she is "the most important person in his life", but that they can't be together because she'll just be unhappy with him. And then Mirai gets infected by a parasite youmu, becomes Brainwashed and Crazy and tries to kill Akihito and all of her friends. Thankfully, Akihito and Mirai finally get (back) together at the end, and in fact it's their love for each other that defeats the Big Bad.
- Spidey and Mary Jane. Dating a superhero makes you a target of hundreds of supervillains. Marrying him means the writers want to break it up as much as possible. And yet, because this is the web-slinger we're talking about, things could be even worse.
- The Trope Namer is the The Magic School Bus Fan Fic First Impressions Of Earth, which has since been deleted. The story's main pairing is Arnold and Phoebe, but it puts them through eleven years of torture including an abusive stepchild, a car crash, a miscarriage, and infidelity, causing Phoebe to have a Heroic B.S.O.D. that culminates in a mental breakdown. And that's just the halfway point.
- In Jus Primae Noctis this is downplayed but present. Louise and Saito keep suffering interruptions to getting around to Their First Time, but nothing to horrible to cope with.
- In Hancock Hancock and his one true love are destined to be apart forever, because if they're together much their powers leave them and they eventually die. This has happened to their entire race; only she and Hancock are still alive.
- In A Brother's Price, Jerin falls in love with a princess. As he's a commoner, problems ensue. Then, more problems ensue because one of her sisters doesn't want to remarry. After that is resolved, Jerin is kidnapped. His sisters, who play only a minor role, manage to find a husband without so many complications.
- Percy Jackson and the Olympians: At the end of The Last Olympian, the Official Couple Percy and Annabeth are together complete with an Underwater Kiss. In The Lost Hero the major plot point is the disappearance of Percy. Then, in Mark of Athena, they end up falling into Tartarus. When shippers said they'd ship the pairing to Tartarus and back, they didn't know it would literally happen!
- Nineteen Eighty-Four: Winston Smith and his love interest, Julia, take part in This and That, rebelling against the system. Then, with The Reveal, O'Brien is found to have turned them in and takes part in re-institutionalizing them into the system. They are reunited at the end, if briefly, but it turns out they have no feelings for each other anymore.
- Vicky Holmes, the Erin Hunter author who writes the storylines and makes the major decisions for the Warrior Cats series, often jokes that she likes doomed romance. And apparently this is true:
- Graystripe and Silverstream are from different Clans, and it's very difficult to meet and even see each other, since their relationship is forbidden by Clan law. They're thrilled when Silverstream's expecting kits, but then she suffers Death by Childbirth.
- Oakheart and Bluestar were also from different Clans. Bluestar became pregnant with his kits, and he offered to join ThunderClan to be with her. However, she stood a good chance of becoming deputy - she wouldn't be eligible for the position with kits - and she felt it was her duty to become deputy since she felt the only other cat being considered for the position would lead the Clan to disaster. Though she wished it could be otherwise, she ended the relationship, and after her kits were born, she gave them to Oakheart to raise in RiverClan.
- Perhaps part of the reason that so many of these Official Couples are doomed is because they're forbidden. Leafpool and Crowfeather's relationship was forbidden in two ways - they're in different Clans, and she's a medicine cat, forbidden to take any mate. They ran off together for a while, but when disaster struck her Clan she realized that they needed her more than he did. She secretly had his kits a short time later. He took a mate in his own Clan, though the authors have described that as a "marriage of convenience", and they seem to argue every time they see each other afterward - and he refuses to acknowledge Hollyleaf, Lionblaze, and Jayfeather as his kits. Despite this, they still have some feelings for each other deep down, even though they never get back together.
- In a rare non-forbidden example, Brambleclaw and Squirrelflight. They became best friends after going on a long journey together, even though initially they were always irritated by each other. Their relationship was tested when he began to follow his evil father, and associate with his half brother, who made no secret of his dream to rule all the Clans, and there was a bit of a Love Triangle when Ashfur showed interest in her as well. Their relationship was eventually mended, and StarClan sent a vision of the two as mates, walking into the sky with stars trailing behind their paws in a single path - their destiny intertwined. Everything seemed fine - they had kits. Then it was revealed that they weren't actually her kits; she'd been covering for her sister Leafpool, who, as a medicine cat, was forbidden to take a mate. They barely spoke to each other for at least two years, until Brambleclaw became leader and chose her as his deputy, admitting that she'd always done what she thought was right. The authors have said their relationship probably won't get back to where it was, but he's forgiven her to an extent.
- Dawn of the Clans starts out with an official couple of Clear Sky and Bright Stream, but then Bright Stream gets killed by an eagle. And just when you think that Clear Sky and Storm will work out, Storm leaves and dies, forgiving Clear Sky with her last breath. This ends up breaking Clear Sky pretty hard.
- Harry Potter does this to Ron and Hermione (usually played for laughs). Order of the Phoenix plays it straight with Harry and Cho.
- The Mortal Engines series is effectively the narrative of this happening over an eighteen-year period with Tom and Hester, culminating in his death from a heart attack and her suicide over his dead body.
- His Dark Materials makes Will and Lyra go through Hell (figuratively) individually, meet, go through Hell (literally and figuratively) together, and then have to leave each other in Alternate Universes because doing so is the only way to save the multiverse.
- This is a fundamental trait of the Sword of Truth series. Richard and Kahlan have been in love since early in the first book, but the increasing turmoil in the setting means they have to deal with separation, invasion, apparent betrayal, and ultimately save the world ten or twelve times before (and after) they can be together.
- In Íverenskommelser by Simona Ahrnstedt, Beatrice and Seth have an extremely difficult time. To be fair, it partly is their own fault, but they also have to deal with three villains, who do everything to keep them apart. It takes them twenty months and alas, Beatrice being raped and almost killed before they can solve their misunderstandings and find happiness together.
- The Hunger Games: Played up in-universe for Katniss and Peeta, especially in "Catching Fire" when they are forced to go back into the arena. They're not actually a couple at that point and their relationship is a facade for the Capitol audience but it becomes real soon enough.
- Han and Leia in Star Wars Legends. There's the stuff that happens onscreen in the movies, then in the books there's the death of Chewie,the entire Yuzhaan Vong war, the death of their son Anakin, the galactic civil war and fighting with Luke, their older son turning to the Dark Side and killing his aunt...not to mention far too many kidnap and assassination attempts over the years. Luke and Mara kind of fall into it, but to a lesser extent. There is the whole thing with her illness and pregnancy during the war and the stress of the aforementioned civil war and Han and Leia ending up opposing them briefly.
- As the World Turns: Luke and Noah of Soap Opera who were supposed to be a couple with problems, but Reid, the intended Romantic False Lead for Luke, became extremely popular with the fanbase. In an effort not to upset either ship, and being pressed for time, Luke didn't end up either of them. Reid was killed off near the end and a grieving Luke didn't get back together with Noah.
- Played straight with the most of the other couples, such as Holden/Lily and Carly/Jack who have gotten married multiple times (though not always to each other) and ended up together by the finale.
- Friends: A thousand times Ross and Rachel. The writers admitted they planned to keep milking their issues until the end of the series, so by the end it's hard to remember they ever had a relationship at all. Averted with Monica and Chandler who didn't break up once. After upgrading from Friends with Benefits to a serious relationship the pair stayed together, in-love and ended Happily Married. They also retained the fandoms patience.
- In CSI: NY Danny and Lindsay have a mid-strength case of this syndrome. First, Lindsay pulls back because of what she's going through with the aftermath of a traumatic childhood incident she survived. Then,after a boy Danny's caring for is shot, Danny pulls away and even sleeps with the kid's mother once. After they get married and Lindsay has his baby, Danny is shot and temporarily paralyzed. Then barely a year later, they and their daughter are stalked by a deranged criminal who blamed Danny for losing his idyllic image of his brother. He battled Danny during the family's first vacation, and they only escaped because he was knocked over the railing of a lighthouse. Then, he shows up in their apartment, holds their daughter hostage and wants to kill all of them. Only Lindsay stops him. Then a year after that, there's Danny as a sergeant, getting grilled by IA because one of his rookies shot the wrong guy. The cop who did it accuses Danny of cheating because she's scared to tell the truth, and Lindsay has to pressure her to tell what really happened.
- Buffy and Angel on Buffy the Vampire Slayer. The fact that the first time they made love, Angel lost his soul, turned evil, and then tried to kill Buffy and end the world only later to have his soul brought back just in time for Buffy to have to send him to a hell dimension in order to save the world illustrates the point. Or perhaps Buffy's later quote when Angel was complaining of her current association with Spike does "What was the highlight of our relationship: when you broke up with me or when I killed you?"
- Also to a lesser extent Tara and Willow with Tara first being sent crazy by the Big Bad and Willow's later magic addiction.
- This certainly happened to many of the principals on Angel's spinoff. The show began to ship tease Ange/Cordelia in Season Three, ending with a planned romantic rendezvous at the disastrously-picked Point Dume. Cordelia was literally roadblocked by a higher power and beamed up from her car, while Angel was tazed and nailed inside a coffin at the ocean's bottom. When Cordy was redeposited on Earth, she inexplicably came down with amnesia (that old chestnut). She eventually became a secondary Big Bad of Season Four, being puppeteered by her own fast-aging, fallen angel offspring, before landing herself into another coma. She did return in time to assist Angel in "You're Welcome" and confess her love, but her brain activity had already ceased by that point, and the Cordelia he'd seen was just a temporary astral projection.
- The slowly developing and frequently sidetracked relationship between Chuck and Sarah is the meta-plot of Chuck. A later season episode implies that Sarah fell in love with Chuck on their very first meeting in the very first episode.
- They officially got together only once and were together for the rest of the series. Outside love interests never came between them again and there was never any threat of a break-up. They did, however, continue to take turns getting kidnapped and almost dying.
- Stefan and Elena from The Vampire Diaries. Their romance and relationship drives the plot of the entire series. Although Stefan and Elena have endured endless obstacles (varying from minor to major) trying to keep them apart, Stefan and Elena still manage after all the problems to come back together, surprisingly stronger then ever before. Some minor examples throughout the series include Stefan pulling away from Elena because of his secret blood issues in season one. Another minor example is Stefan and Elena breaking up because of Katherine threatening to harm everyone Elena loves in season two. One major example is in season three, Stefan sacrificing himself to Klaus in order to save Damon's life and protect Elena. During this time, Stefan left Elena and Mystic Falls, turned off his emotions (his humanity) and became a Ripper. With Stefan being a Ripper with no emotions, Stefan had almost tried to kill Elena by biting her under Klaus compulsion. Despite Stefan not feeling anything, Elena was determined to bring Stefan back and get him to turn on his humanity again so that he could feel. This was a huge obstacle and struggle that Stefan and Elena faced in the series. Regardless of how bad or awful things get, somehow, Stefan and Elena manage to overcome the problems, be together happily as if nothing ever happened and come back together as a couple stronger then ever before.
- Luke and Lorelai of Gilmore Girls. After four seasons of UST, they start going steady and even got engaged at the end of the season. The wedding gets called off when Lorelai realized that Luke found out about a secret love child of his and didn't tell her about it. Lorelai even somewhat lampshades the trope when she realizes that all of the wedding preparations were going by perfectly and was expecting something to go wrong along the way. By next season, showrunner Amy Sherman-Palladino and her husband weren't working on the show anymore, leading to nearly an entire season where Luke and Lorelai were broken up. Everyone knew they would get back together because advertisements for the show continued to show the couple together, it was just a question of when they would. It wasn't until the last few minutes of the series finale that they renewed the relationship.
- Up to Eleven on Spartacus: Blood and Sand. Granted it is a show about people who have been enslaved and stage a Gladiator Revolt. Naturally this makes their romantic lives complicated to put it mildly. But even the comparatively well-off Roman elite tend to have relationships of the Unholy Matrimony or Destructive Romance sort. Nobody has a drama-free relationship!
- Crichton and Aeryn on Farscape. It starts with Aeryn's Peacekeeper training and associated baggage cooling her on the thought of romantic attachments. Then they start to fall for one another, leading to a kiss that scares Aeryn and Crichton's subsequent marriage to a planetary royal. Once that gets resolved they ramp up the Will They or Won't They? until the season 2 finale when they confess their love for one another. Unfortunately, Crichton is being controlled by Scorpius's neural clone and bashes Aeryn's head in right after. And then later in the episode Aeryn dies. She gets better in the season 3 premier and they finally say "I love you," but the Heroic Sacrifice by Zhaan to revive her leads Aeryn to insist on not acting on it. Then Crichton gets duplicated, and the crews split up to escape Aeryn's mother. Aeryn and Crichton on Talyn get together for real, and then Crichton dies in a Heroic Sacrifice (and this Crichton stays dead). So when the crews reunite on Moya, Aeryn turns cold and wants nothing to do with the surviving Crichton, and eventually leaves him behind at the end of the season when she goes off on her own. By the time Crichton and Aeryn reunite in season 4 she's now decided she wants him back, but now Crichton is giving her the cold shoulder with the aid of drugs given to him by Noranti. Aerynfinds out about this and reads him the riot act, at which point they finally get together for good. And then Aeryn gets kidnapped and tortured by the Scarrans. By the time Crichton gets her back and they defeat the plans of the Scarran Emperor in the series finale, the couple finally settles down to catch their breath, at which point Crichton proposes marriage to her, and Aeryn accepts. And then they get vaporized by an alien spacecraft in the cliffhanger ending (Farscape was originally signed for two additional seasons, but was cancelled). Fortunately, the miniseries finally gives them their happy ending. Whew!
- Once Castle and Beckett upgrade their relationship, this takes a pretty big turn. It goes like this, per season ender:
- Season 3: Castle declares his love for Beckett as she lay motionless from a sniper bullet.
- Season 4: After Beckett nearly dies, she realizes she only wants Castle, and They Do.
- Season 5: Castle proposes to Beckett just as she takes a job with the Justice Department in Washington D.C.
- Season 6: Their wedding is interrupted by mysterious men who run Castle off the road, kidnap him for 2 months, then erase his memory of what happened.
- They finally get married in mid-Season 7.
- Season 8: Marriage hasn't stopped the trope. A hitherto unknown enemy related to Beckett's mother's murder surfaces, and she has separated from Castle to pursue her own private investigation into this. She's gotten multiple speeches from people who've been in her shoes basically asking her what the hell she's doing. But she's already set her mind to this.
- Romeo and Juliet, the original Star-Crossed Lovers: Initially, both are greatly in love with each other. However, as the plot moves past the romance, kin and family are killed: Mercutio for Romeo and Tybalt for Juliet. As both are torn by grief, they are at risk of being separated by their Feuding Families. With both families ready to destroy each other by play's end, Romeo and Juliet both commit suicide in grief at having lost each other. Juliet was under the effect of a potion and appeared dead. Romeo proceeds to commit suicide and Juliet follows suit after him.
- This also occurs in Othello, climaxing in Othello murdering Desdemona and killing himself. Even worse, the entire plot was being carefully choreographed by Iago.
- At the beginning of Starcraft II Heart Of The Swarm, after a very long series of confrontations and problems of all kinds which even involved one giving a death threat to the other as vengeance for killing a friend, Jim Raynor and Sarah Kerrigan finally get the Official Couple status, despite the fact that it doesn't last as much. Starcraft II Legacy Of The Void puts them through even more before an ambiguous Stinger that seems to finally let them have their happy ending.
- Mortal Kombat X has Johnny Cage and Sonya Blade, who, after surviving two Mortal Kombat tournaments and Outworld's invasion to Earthrealm, after all is said and done, hook up and even have a daughter, Cassie Cage.
- School Days is likely the darkest and edgiest this trope will ever get. Though the Official Couple were Makoto and Kotonoha. Makoto and Sekai proceeded to sleep together. Makoto sleeps with just about everything that moves. In the end, depending on what rendition of School Days you are referencing, we have variations of Sekai murdering Kotonoha and Makoto to Kotonoha murdering Sekai.
- Fate/stay night in the Fate route/Anime. The Saber-focused Fate route has Shirou and Saber come to love each other. With the war at an end we get a Bittersweet Ending with the romance entering Star-Crossed Lovers territory. With the Big Bad and his Dragon defeated, the Holy Grail war ends, Saber returns to the past to finally allow her body to die and complete the myth of King Arthur. If you play the PS2 port and complete EVERY single requirement, the Revised Ending allows Saber and Shirou to be together. Even if it's in death.
- Dad Egbert and Mom Lalonde from Homestuck. They may be an Official Couple, but that doesn't mean they're exempt from being killed off.