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Love Hurts

"Love hurts, love scars,
love wounds and marrs any heart
not tough or strong enough
to take a lot of pain, take a lot of pain..."
— "Love Hurts'', written by Boudleaux Bryant and recorded by The Everly Brothers/Nazareth/Cher/etc. (possible Trope Namer)

Forget life-threatening superheroism, acting Too Dumb to Live, and Tempting Fate. The most dumb, insane and dangerous thing any hero can do in any media is... falling in love. Dare to love someone else and you set up yourself and your beloved for a plethora of emotional griefs. Love in Real Life is responsible for vast quantities of anguished poetry and tragic literature; factor in all the crazy stuff that happens on TV, and drama and disaster are practically guaranteed.

About to commit permanently? Look for an Anyone Can Die to put a permanent end to the Will They or Won't They? issue. Forget to say goodbye to your beloved that one time? It'll haunt you for the rest of your life. And let's not forget that becoming emotionally attached to one person leaves you open to the stress caused by the villain abducting your beloved or them even being killed off senselessly just to shape you into the Anti-Hero out for Revenge, or at the very least a Heartbroken Bad Ass. Your love is hurt but alive? Don't You Dare Pity Me! — they will shove you away. Or perhaps you'd be their Second Love — if only they and you didn't think Silly Rabbit, Romance Is for Kids!. Love will make your heart go soft and pitter-pattering into the path to be crushed by the cruel forces of fate against Star-Crossed Lovers. Small wonder that so many try to protect their loved ones by dumping them.

If you've got more than one love interest, you've got a headache-inducing Love Triangle or even Love Dodecahedron on your hands. Tread these waters very carefully, lest you be on the receiving end of a Yandere's poisonous affections or a Tsundere's Megaton Punch. Pick one lover and you can look forward to either a Thundering Herd of jilted rivals or the silent shattering of many other hearts. All in the name of comedy, you say? Comedy never became as twisted as it does when dealing with lovers crazy enough to beat down your door, commit trespassing, glomp you, and refuse to let go. And remembering the love interest anywhere you go makes it worse.

And heaven forbid if your love turns out to be one-sided. You'll become a crazy Love Hungry psycho stalker if you don't choose to nobly sacrifice your love. Sometimes you'll even go all the way into a full-fledged villain with a grudge against humanity because humanity was not kind enough to let you have that one person. Sometimes it's even your own creator who decides that you can't get them because he couldn't get her in real life!

Such a fragile illusion... Isn't it?

In the right/wrong genre, even when you win, you lose. Little wonder why many a pessimist believes that "Silly Rabbit, Romance Is for Kids!" and Love Makes You Dumb, and many a hero has chosen to be a Genre Savvy Celibate Hero.

Compare Destructive Romance, Hope Is Scary.

However, if you do manage to get it right, love can be the purest and most powerful thing in the world. Another way to resolve this is through Cleaning Up Romantic Loose Ends.

Contrast Happily Married. Unrelated to Lover Tug-of-War, even though that may also hurt.

Examples

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    Anime and Manga 
  • Anemone and Dominic of Eureka Seven. The dangerous drugs she uses to pilot her mech take her Domestic Abuse Tsundere type behavior way beyond the usual fare. Sure, it can be funny at first to watch her beat the stuffing out of him, but as you gradually realize the depths of his devotion, her cruel indifference or abject violence becomes incredibly painful to watch. On Anemone's side, when she finally realizes how much he means to her, but believes it's all too late, she delivers a gut-wrenching soliloquy, convinced that she doesn't deserve to live. Amazingly, it all manages to end well.
  • Dokuro-chan from Bludgeoning Angel Dokuro-chan is an extremely brutal and literal version of this. The Opening probably puts this best:
    "I'll cut you, punch you, toy with you
    Kick you, be a cocktease, drip stuff on you
    But that's just how I express my love."
    • Dokuro may not even be in love with Sakura. Read the WMGs for that series.
    • Apparently, the main reason for Erika's obsession with the truth and her What Kind of Lame Power Is Heart, Anyway? tendencies is because of a failed relationship with her boyfriend.
  • Roy/Riza in Fullmetal Alchemist. Even aside from the whole burning her back thing, they have been a massive source of pain for one another. Most of the traumatic events they have gone through would most likely never have taken place if they hadn't met each other (Roy wouldn't even be a State Alchemist, she wouldn't have joined the army and been sent to Ishval and he wouldn't have annihilated so many people; she has made it clear she doesn't like being in the army or killing people, but she won't quit as long as he needs her). They're practically the direct (albeit non-intentional) cause of everything in the other's life that makes them suffer, and still they're the very thing that makes the other want to go on living as stated outright in chapter 95.
    • Riza has her throat cut to force Roy to open the gate. Riza signals with a glare that not only would she beat him to death if he committed human transmutation, but help was on the way so it was pointless. It was nice of Arakawa to not force Roy to choose between the two options, though when you think about the fact that he was seriously considering damning Amestris (and, possibly-eventually the whole world) for saving Riza, and couldn't even come to the decision to not do human transmutation till it seemed she would be saved you get a little worried at the lengths Roy would go to to keep his Lieutenant by his side.
  • Pick practically ANY hero in ANY Gundam series. If you don't believe me...
    • Mobile Suit Gundam: Amuro Ray accidentally killed Lalah, his first love, when she took an attack meant for the man she loved, Char Aznable.
    • Zeta Gundam: Kamille Bidan had his star crossed soulmate Four Murasame sacrificing herself for him twice. Oh, and his sworn rival Jerid Messa losing both of his love interests (Dark Action Girls Lyla Mira Lyla and Muar Pharaoh) to Kamille, so they can call it even.
    • Gundam ZZ: Judau Ashta loses Chara Soon, a broken young woman he didn't romantically love but still quite cared about, mere seconds after making her promise that she wouldn't die. He then proceeds to have to kill Haman Karn, one of his principle love interests, in the final battle.
    • Victory Gundam : Even though nearly every couple in this series doesn't end well, the main character's crush on Katejina ends up very badly since she becomes an enemy AND in love with the resident Char Clone too!
    • Roybea Roy, the resident Chivalrous Pervert of Gundam X fame is well aware of this, its the reason why he chases away most of his lovers before he aligns with the Freeden crew. This doesn't stop him from falling in with a female member of a La Résistance, who then dies in his arms.
      • Ennil El happens to fall for The Hero Garrod, who, wanting nothing to do with her, aims a gun in her face, she becomes a Stalker with a Crush who follows the Freeden wanting revenge.
    • Gundam SEED: Kira Yamato was manipulated by his first girlfriend, Flay, and later saw her die in front of him. Also Murrue Ramius, whose heart goes on. Twice. At least one of them returned in the following series.
    • Gundam SEED Destiny: Shinn Asuka fell in love with Stellar, who also died in front of him, despite his promise to protect her.
    • Not content to ruin just one couple, Gundam 00 has destroyed several of them.Feldt lost her first crush before she even had the chance of admitting anything to him, and ditto for Tieria who was in love with the same man that Feldt loved; Christina and Lichty were already dying when they conceded that they had feelings for each other; Saji's relationship with Louise is to put it very nicely "on the rocks"; Allelujah and Soma's has also hit some rough ground with the death of Sergei Smirnov; Lyle, the twin brother of the guy loved by Feldt and Tieria, just saw his lover Anew get blown to pieces by Setsuna before his very eyes; Sumeragi's lover Emilio was already dead prior to the series beginning and then what relation she may have had with Billy got torn up when Setsuna opened his mouth about her being part of CB
    • Flit Asuno from Gundam AGE fell for Yurin L'Ciel, only to see her get manipulated and later brutally killed by Desil. He becomes so enraged and psychologically broken that he not only refuses to acknowledge the UE as fellow human beings, but also starts to see himself as a savior... for the corrupt and genocidal Earth Federal Forces.
    • Among those who got off (relatively) easy are:
      • The 08th MS Team: Shiro Amada only loses a leg, but he keeps Aina and they live in peace.
      • Gundam 0080: Christina Mackenzie is completely unaware that she killed Bernie.
      • G Gundam: Domon Kasshu almost lost Rain to the same Devil Gundam that caused the deaths of many others, including his beloved older brother. But he managed to save her and get her back... in the most awesome way EVER. Also, Allenby escapes the fate of most Brainwashed and Crazy women because the person who fights her is Rain, who has a Gundam equipped for precision and is a doctor. Rain brings her down without deadly force and defuses her, leaving her with just a brief hospital stay.
      • In Gundam X losing Tiffa Adil causes Garrod a Heroic BSOD, it didn't last long.
      • Gundam 00 (again) Saji and Louise got back together; Alle and Soma survived their Battle Couple stint and went Walking the Earth; Sumeragi talked Billy outta his funk and they kinda reconciled; Patrick survived too and he and Kati got married.
      • Gundam Build Fighters: As expected of the most light-hearted Gundam series yet, the romance (confined mostly to Ship Tease) results in far more comedy than angst. Reiji and Aila face the most obstacles, but like almost everyone in the series, they get a happy ending.
  • Then, pick any hero in any Gundam-inspired series.
    • Space Runaway Ideon: Cosmo suffers a Heroic BSOD discovering that a girl he grew fond of, Kitty Kitten, was killed almost accidentally. Later, Kasha Imhof dies in the movie... and then EVERYONE dies..
    • Neon Genesis Evangelion: This is Gendo's Freudian Excuse.
    • Code Geass: Suzaku witnesses his big love Princess Euphemia fatally shot by his arch-nemesis, after which she effectively dies in his arms (Pietà Plagiarism galore), then some fifteen episodes later Lelouch, the said "arch-nemesis", experiences Shirley, a girl he always cared for (well, perhaps not romantically but it was definitely headed that way) dying on him in a very similar fashion... at the hands of his Gay Option of sorts, a Yandere boy who later commits suicide to save Lelouch's own life..
  • Ayumi from Honey and Clover has a bad case of unrequited love for Takumi, who sees her more like his sister. A lot of the first season of the anime is devoted to Ayumi's suffering because of this. Takumi in turn has a hard time with his feelings for (older) Rika.
  • In One Piece, "Pirate Empress" Boa Hancock of the Seven Warlords of the Sea has the power to turn anyone who's so much as attracted to her to stone. And then when she herself falls in love, she might die by it.
    • This is actually subverted when Hancock falls in love, given that she has decided to help Luffy rather than bottle her feelings within her, as that was the cause of death for two empresses before her, and almost killed the elder/ex-ex-ex empress herself. Except that even though her feelings are sincere and intense and based on how he once defeated the Tenryuubito aka those who enslaved and tortured Hancock and her sisters as young girls, it's almost depressingly apparent that she doesn't really have a chance with Luffy. Though, in all fairness, she has as much chance as any other woman with Luffy, the ultimate Idiot Hero with a degree in Oblivious to Love.
    • It's also painfully obvious Camie the mermaid has a pretty serious thing for Hatchan, but...well...same reasons as above.
    • Sanji would be the king of this trope if he ever realized none of the women he's encountered (aside from the man-ladies) ever showed any interest in him.
    • Depending on how you interpret the relationship, Zoro towards Kuina. When you put the possibility in context with his present lack of interest in sex, it makes his back story even more depressing.
  • Lithuania in Axis Powers Hetalia gets all his fingers broken by his crush, the eccentric Yandere Belarus. He doesn't seem to mind. Russia, who is both Lithuania's boss and Bela's older brother (and more of a Yandere than her), has a very twisted, rather one-sided relationship with Lithuania himself, showing his affections through stalking and abuse.
  • Good God, Franz from Gankutsuou. His unrequited love for Albert caused him a whole world of pain (and his death). Seriously, he had a lot going for him - being rich, having good looks, and having no shortage of beautiful and kind women after him (including his fiance, who loved him initially). But instead, he ends up constantly angsting and sacrificing everything for Albert (who doesn't appreciate any of it until the very last moment).
  • In Chobits, Freya essentially kills herself because of this trope.
  • In Gantz, Kei goes through severe depression multiple times due to his loves dying on him. The first time is when Kishimoto dies (although she never did return his feelings), and subsequent times of him becoming really depressed are caused by his girlfriend Tae (who died but got revived). And since the series is still going on, there's still no guarantee that they'll be able to be together. A Downer Ending is quite possible...
  • Ako Izumi of Mahou Sensei Negima!. She has a ton of self-esteem issues, and is described as something of a doormat. Then she meets Nagi, he reassures her of her importance, and she falls in love with him. Even after getting Trapped in Another World and sold into slavery, she's able to hang on because she knows that he's there for her. Too bad that "Nagi" is her ten-year-old teacher Negi magically aged-up. Naturally, she's utterly crushed when she finds out. And then, she gets better, sort of; she still has a thing for 'Nagi'. Which may be transferring to Negi now.
  • Sagara Sousuke from Full Metal Panic! towards Kaname. His whole Heroic BSOD in TSR was caused by being torn away from her after he developed an attachment and feelings for her. As Gauron angrily notices, ever since falling in love, he seems to have a lot more conflicting feelings and doubts.
    • And speaking of Gauron, he seems to have lost some of his edge and become even more messed up since falling for Sousuke... after all, if he didn't care about Sousuke, he wouldn't have been so very angry in the first place...
      • In regards to Gauron, this is actually brought up and symbolically implied in the novels (though apparently parts of it were lost in the fan translation). Members of Amalgam actually covertly bring up to Sousuke how Gauron was overtaken by "cancer," all while mentioning that he "really really liked Sousuke"... and according to the original wording, a parallel is implied of Kaname being Sousuke's "Gan" (cancer), and Sousuke being Gauron's "Gan". Any possible double meaning was lost to Sousuke. In addition, reading about the overall attitude of Gauron's colleagues when they talk to Sousuke, it seems like it's a well known fact to them that Gauron was way too obsessed with Sousuke.
  • RahXephon: Hey Megumi. What's that, your crush already has a girlfriend who is your best friend? Ouch. Now what about that other guy? Sorry, your sister Haruka already had the key to his heart long ago. Oh, and the other other guy? Turned evil because of the death of the girl he loves.
  • Jigen from Lupin III. His luck with women runs from bad to worse, with them either betraying him, dying, or both.
  • Simon from Tengen Toppa Gurren Lagann. His first love, Cool Big Sis Yoko, was in love with Kamina, and he had a rather painful experience seeing her kiss him. Seeing said kiss would lead to Simon suffering a Heroic BSOD, that resulted in Kamina's death. His Second Love, Nia, ends up dying right when they get married. And whether you interpret the relationship between him and Kamina as Ho Yay or as Heterosexual Life-Partners, it is undeniable that Kamina's death hit him very hard.
    • Yoko had it pretty hard too: the event that changed her from a Tsundere to a Cool Big Sis was Kamina's death. Which happend on the very morning of their first kiss right after he promised to give her something ten times better when the battle is over ...damn Retirony.
    • Must have also hurt Kittan badly when he only had the confidence (and partly because of it) to confess to Yoko before performing an EPIC Heroic Sacrifice to spare her from doing the same...
    • And there's Viral, who is immortal and can't reproduce... and whose greatest dream is to have a wife and child. *sniff*
  • Kenshin Himura and Tomoe Yukishiro from Rurouni Kenshin. When he was in his Extreme Doormat phase, she was the one that made him start feeling anything at all again. Apparently it was first caring, then love, and finally awful grief. He has his fair share of Love Hurts moments with his second girlfriend Kaoru too, but his story with Tomoe steals the show.
    • It's also a whole deal for Tomoe herself. She lost her Victorious Childhood Friend Akira to Kenshin's sword, went to Kyoto to find him and have revenge, but once she knew Kenshin better she fell for him. And she died. Horribly and tragically.
  • Basilisk, has poor Oboro and Gennosuke. They were engaged to bring peace between their two rival ninja clans but genuinely fell in love, only for the truce to be broken and forcing them to choose between their love or the honor of their clans. In the end they are the only two left alive, and Oboro commits suicide rather than kill Gennosuke. Gennosuke declares Oboro's clan as victorious and commits suicide with her body in his arms.
  • In Magic Knight Rayearth Hikaru and Lantis had it pretty bad. She killed his brother without knowing the true story behind his actions, then spent the entire second season caught between falling in love with Lantis and feeling heartbroken because he probably hated her for killing his only family. Lantis didn't have it any easier. Though he didn't hold her accountable and wasn't averse to loving her after she unknowingly revealed her feelings for him, it all went downhill when she was chosen as a candidate for the Pillar... thus threatening to repeat the tragic romance of his elder brother and the former Pillar Emeraude. Hikaru managed to destroy the Pillar system later on but still was forced to go back to her world after saving Cephiro in the end.
  • (Almost) everybody in Itoshiki-sensei's class loves their Zetsubou-sensei. Too bad every single one of them is in some way severely unhinged.
  • Tails and Cosmo from Sonic X were the cutest and sweetest couple ever, but just at the series end, Cosmo must fuse herself with Big Bad Dark Oak planet to weaken it, so Tails (from all people, to boot) could fire his ship's supercharged cannon to destroy it and save the universe, killing Cosmo and crushing his heart in the process. To make it even worse, Sonic and Shadow's attempts to revive Cosmo ends up in a total failure, leaving a completely broken Tails lying on the floor, crying his soul out.
    • Not a total failure. They managed to get a seed that they imply will grow back into Cosmo with all her memories intact.
  • Naruto. Titular character's love for Sasuke (whether romantic or not) has torn his heart apart ever since he defected. His one-sided shallow crush on Sakura at the beginning didn't give him anything nicer until the end either. Poor guy can't even be relaxed in a mutual romance when he confesses to Hinata in The Last: Naruto The Movie, he gets rejected over a Break His Heart to Save Him, finds out she's getting married to Big Bad which leads him to Heroic BSOD until his friends snaps him out. Fortunately he gets to Earn His Happy Ending with all of the listed above.
    • And Sakura herself hasn't had it easy either because of Sasuke ( whom she has decided to kill with her own hands to spare him from more grief and betrayal.) At the end of manga She finally Earns Her Happy Ending by getting married to him
    • Naruto is RIFE with this, whether romantic or not. There's Hinata, who takes a suicidal attack to protect Naruto, whom she loves because he gave her the will *to not give up ever again* ; Gaara, who only wanted to be loved, but was hated by everyone until he befriended Naruto, and later cries when facing Sasuke; Konan, whose love interest is none other than Pain; Jiraiya, who was Tsunade's Unlucky Childhood Friend; Kakashi, who learned what friendship and love were when he lost his best friend Obito and then rejected Rin's love for him.; etc.
  • Cowboy Bebop: The tragic love between Spike and Julia.
  • Many all the clients or people they know in Nightmare Inspector are in love with someone, and if they aren't evil, mad, or downright psychopathic from it, they're suffering a good deal.
  • Akuyuki and Haru (especially Haru) suffer through so much of this Xam'd: Lost Memories.
  • This is the lesson learned in Apollos Song, where a young sociopath with a pathological hatred of love is condemned by the goddess Athena to live through a series of tragic love stories.
  • In Maiden Rose, the main characters' relationship is the reason their lives are so miserable and screwed up. Their relationship is also exactly why they're both willing to put up with all the misery as they couldn't stand living without each other.
  • One of Hinagiku's fears in Hayate the Combat Butler is based on this, and it's implied that her fear of heights extends from this. She's afraid of loving someone because her parents left and her older sister has turned to drinking after making sure that Hina doesn't have to deal with the debt and has foster parents, thus she's afraid of loving anyone again, in an effort to keep from getting hurt by them. She may have even turned to her Tsundere personality because of it. Her admitting (to Ayumu) that she does love Hayate has been shown as an effort because of these fears.
  • Puella Magi Madoka Magica. Sayaka Miki, who becomes a magical girl so that her crush's permanent injuries heal (despite being warned that it won't work the way she wants to), loses said crush to her friend because she is essentially a zombie as result of being a magical girl leading her to feel that she's unlovable (and thus when said friend does give her the chance to confess first to the boy, she cannot take it.) She becomes increasingly self-destructive ending with her turning into a witch, the creatures that magical girls are tasked to fight. In the end when the universe is reset to give all magical girls a happier life Sayaka still ends up dying. Word of God says that, in any continuity where she becomes a Magical Girl, she'll be damned to this and can't be saved.
  • Ranma ½: While many of the romantic hi-jinks are Played For Comedy, it is obvious that all the girls in Ranma's harem are in love with him. Shampoo is probably the most blatant and forward with her feelings for Ranma, concocting multiple schemes to win his heart while brushing off the similarly strong if not stronger affections that Mousse has for her. Ukyo strives to actually be seen as a "woman" by Ranma, while Konatsu probably wishes for Ukyo to see him as an actual man. Kodachi is difficult to place as she is crazy but she does seem to generally have honest feelings for Ranma. She claims that she knows that he doesn't feel the same way but is determined to keep trying. And that brings us to the Akane. Akane is in love with Ranma. There are just a couple of things that stand in the way of their romance actually going anywhere.
    • Akane also goes through this for years by having a crush on Dr. Tofu, a man who's in love with her sister, Kasumi. It isn't until she's 16 that she finally moves on and develops a crush on Ranma.
      Akane: You can stop your feeble attempts to cheer me up now. I've got a broken heart, remember?
      Ranma: Well, then...
      Akane: Then what?
      Ranma: Then you gotta realize that these things happen.
  • The plot, point, story and character motivation of Minami Ozaki's Zetsuai 1989. Period. Even the bystanders get traumatized by the events.
  • In chapter 40 of Rosario + Vampire, it is revealed that succubi can die from heartbreak, which seems to be happening to poor Kurumu.
  • GE - Good Ending has this all over the place with all the girls, but specially Utsumi, the main protagonist.
  • Akise Aru of Future Diary has an unreturned crush on Yukiteru and all his actions of love towards Yukiteru get him is a beheading by Yuno.
  • Rune from Karakuridouji Ultimo has an unreturned crush on Yamato and he doesn't take rejection well. His love for Yamato causes him a lot of heartache.
  • Kagetora and Naoe's relationship in Mirage of Blaze.
  • There's loads of this in D.N.Angel. For example, there's Daisuke's unreturned feelings for Risa who has a crush on Dark who he sees kissing Risa at one point breaking his heart.
  • Harry MacDoogal from Outlaw Star. You've got to feel for him because he has feelings for Melfina and she doesn't share the same feelings for him and he does everything he can to make her love him only to fail and get curb stomped by a massive douchebag with the ability to break his body parts like a bendy straw.
  • Revolutionary Girl Utena is rife with this.
  • The Guts, Griffith, Casca Love Triangle in Berserk.
  • In Katekyo Hitman Reborn! Tsuna has an unreturned crush on Kyouko and Gokudera is implied to have feelings for Tsuna. His soft spot for Tsuna results in many, many touching woobie moments for him. The fact that he's willing to (and many times does) go through hell and high water for Tsuna who just thinks of him as a friend makes many people just want to give him a big hug.
  • Chaos from Heaven's Lost Property is an unusual spin on this. She believes that pain is love and as a severe Love Freak she seeks to spread her "love" to everyone.
  • Jeremy in A Cruel God Reigns. His girlfriend Vivi breaks up with him after she suspects that he cheated on her (although he was forced into having sex with Greg so he wouldn't break off his engagement with Jeremy's mother) and he spends the next several books not only reeling at Greg's abuse, but mourning the loss of his beloved girlfriend. Poor guy.
    • This trope also applies to Ian and Nadia in later books; Ian, because of his confusion about falling in love with Jeremy despite the latter's slight case of Being Tortured Makes You Evil and Nadia because of her heartbreak over losing Ian to Jeremy.
    • Can also be applied to Sandra when Greg breaks off their engagement because Jeremy refuses him. Also tied in with Sandra's Driven to Suicide and Bungled Suicide.
  • Happens to Bird's Nest a couple of times in Copernicus Breathing, once after he thinks Leo has died in his juggling accident (which then leads to a Freak Out ) and then again when he confuses Michel Bohringer with his dead little brother Michel (twice) (again, Incest Subtext. )
  • When Misaki sees Jin and Mashiro on their date in episode 3 of Sakura-sou no Pet na Kanojo, it really breaks her heart. Later when the two are seen outside a Love Hotel, she decides to go home rather than interrupt them.
    • Sorata also feels this way after seeing those two together. Unlike Misaki, he does interrupt them, but fortunately for him Jin had no intentions of entering the hotel with Mashiro, and set this up knowing both he and Mashiro were being followed by him.
  • Happens to Nanami in Kamisama Kiss when she confesses her love to Tomoe. See Tomoe is Nanami's familiar and a Little Bit Beastly Kitsune while Nanami is a teenage human girl and Tomoe does not approve of Interspecies Romance. So he immediately tries to force her to take back her confession which works out about well as you can expect.
  • Rick Hunter/Hikaru Ichijyo has it pretty bad in Robotech and the original Super Dimension Fortress Macross. For most of the series, he's in love with Lynn Minmei/Minmay. She, on the other hand, has her own issues with her Idol Singer career and is very Oblivious to Love. Of course, Rick/Hikaru himself isn't blameless, as he pretty much ignores the feelings of the much more mature CO Lisa Hayes/Misa Hayase until it's almost too late. And Lisa/Misa has her own Dark and Troubled Past that includes a lost fiancé among other very complicated issues.
  • Jellal Fernandez and Erza Scarlet of Fairy Tail have this hard. They were slaves together as children in the Tower of Heaven and were deadset on one day escaping and living their lives together. Then, their plan was discovered, and Erza was dragged away to be punished. Jellal manages to save her, but is punished with unimaginably cruel torture that, coupled with Ultear's brainwashing, drove him completely insane. Erza rescues him only to have him drive her out of the Tower when she refuses to join him in his madness, and she spends the next eight years dreading the day they'll meet again. Eventually they do, and she's forced to leave him to die after their confrontation. A bit of time after that, he's revived with no memories and completely back to his real personality, but is arrested by the authorities for his previous actions right after they reconcile. Shortly afterward, she is put into a coma for seven years, and when they finally meet again, he pushes her away because he feels he does not deserve her love any longer, though he can't quite keep himself from following her around. Their whole relationship is built on this trope.
  • In CLANNAD when Tomoya's wife dies tragically in childbirth, Tomoya feels that he should never have met Nagisa in the first place, because of the horrible pain her death is causing him.
  • K's Fushimi Saruhiko has an Unrequited Love for Yata Misaki that is apparently so strong that it drove him insane. Because Misaki had found new friends and a new family with HOMRA and started to drift away from him he lost himself in jealousy and heartbreak, believing that making Misaki hate him was the only way to get his attention. The Manga Days of Blue shows very clearly that he still suffers badly over being away.
  • In Umi Monogatari, this is Oshima and Kanon's situation in a nutshell.
    • Kanon realizes that it was her own insecurity that made her feel like Kojima was going to dump her, when in fact he had liked her all along and never intended to dump her. At the same time, Kojima confesses to Marin that he had liked Kanon from the start, but felt she was purposely separating herself from him, and so they grew distant. Kanon realizes that she never told anyone she liked them out loud even once.
    • Oshima initially seems to be your classic Alpha Bitch, but she has heartbreaking hidden depths. She tells Kanon that even when she was going out with Kojima, all he ever talked about was Kanon. She feels she'll never measure up to Kanon in his eyes, and that it hurts to like someone that much knowing they'll never feel the same way about you.

    Comic Books 
  • Peanuts
    • One of the many reasons Charlie Brown is The Woobie is his inability to get the Little Red Haired Girl to notice him. A minor case of Creator Breakdown; Schulz admitted that he had his own "Little Red Haired Girl," whom he lost.
    • If this wasn't so funny, it would be depressing: Charlie Brown is to Peppermint Patty as the Little Red Haired Girl is to Charlie Brown, making it an unrequited Love Triangle. Good Grief!
    • Love Rectangle. Marcie also loves Charlie Brown. Too bad her loyalty to Peppermint Patty requires her to aid and abet her "Sir"'s plans.
    • Indeed, unrequited love is a running theme throughout the comic's run: Linus towards Miss Othmar, Sally towards Linus ("I'm not your sweet baboo!"), Lucy towards Schroeder... the list goes on.
  • Dr Allison Mann in Y: The Last Man angrily denies that love is anything other than a label stuck on a biological process. We later find this apparently cynical attitude comes from Allison being dumped by her first girlfriend (and her parents' miserable marriage). Despite this it is clear she still craves love herself.
  • Any romance in any Marvel, DC, or other company you care to name wherein the relationship lasted more than 3 years real-time/10 months in-universe and the characters, to this day, are not together. Don't even go into the ones that -are- together... Examples are just too numerous to list. Averted with Ralph (Elongated Man) & Sue Dibny, who were happily married in his second appearance back in the 1960s and in death were still together.
  • Explored (somewhat) in Johnny the Homicidal Maniac, where the main character is very much under the impression that this trope is in full effect (and that is only the tip of the iceberg where his intimacy issues are concerned). He attempts to murder the only person he cares for in an attempt at 'immortalizing the moment' and prevent the relationship going bad (because...somehow murder doesn't count as going bad) and later attempts to apologize for the faux pas with a rather bizarre pre-recorded phone message in which he states his intention to forget about her, lest he attempt to hurt her again.
    Johnny: I like you immensely, Devi. And to prove it, I shall obliterate all of my affection and interest for you. Just like before, but different. I cannot hurt what I do not acknowledge. I don't know of anyone that I love, or of anyone that loves me, but I give you what I can. I give my nothing.
  • Rose Walker's great "love hurts" speech to Desire in The Sandman. This exchange sums up Desire's approach to most things but especially love:
    Rose: Are you going to hurt me? Kill me? Mess me up?
    Desire: No more than usually; no; and perhaps a little. But only with love.
  • Scott Pilgrim. No one is safe from that in that comic. Gets to its extremes with Ramona and Knives though. A chapter is even named 'Love Hurts'.

    Fairy Tales 
  • The original version of The Little Mermaid: The mermaid loves the prince and gives up her voice and family to be with him, but he ends up marrying someone else and she turns into sea foam. But a tacked-on Aesop-fuelled ending gives her an immortal (i.e. human) soul anyway. Reputedly fueled by Creator Breakdown. Technically, in the Hans Christian Andersen version, she doesn't get a soul - yet. She get's turned into an air spirit that, after a preset amount of time, will get an immortal soul. As an extra twist, whenever she passes through a house with a well behaved child, she gets a few years knocked off her sentence. Ill behaved children add years. That's right, kids. If you don't eat your vegetables... you're preventing mermaids from going to heaven.

    Fan Fiction 
  • In the Pokemon fanfic A Pikachu in Love, Pikachu gets hit hard with this in the ending, having to say goodbye to Pichi when he finally made his choice to stay with Ash. Misty's comment when she sees it pretty much sums it up.
    Misty: I’m sorry Pikachu... It must have been hard, saying goodbye to someone you love."
  • The Tamers Forever Series uses love as a surgical scalpel to subject the characters to unimaginable suffering.
  • Hunting The Unicorn: Blaine is a Love Martyr who's head over heels for his boyfriend Kurt. Why does love hurt so much? Because Kurt is Blaine's Second Love.
    • Also because Kurt leaves Dalton, but this time we get to see it break Blaine's heart into tiny little pieces because "No-one ever comes back to [him]."
    • It's not just limited to romantic love, since he's vehemently loyal to his estranged, neglectful father.
  • Minako and Shinjiro in Death And Ker get to face just how much love can hurt. Bad enough that Minako died without warning two years prior as a result of a Heroic Sacrifice - worse that she's come back, but only temporarily, and must return to death when her mission is complete, the knowledge of which keeps both of them from feeling able to act on their feelings the way they'd like to. Aigis in the same work has it just as bad; she also loves Minako and blames herself for not being able to protect her two years previously, and since she's a Ridiculously Human Robot she's struggling with the concept of being able to feel human emotions at all.
  • Stars Above: Hoo boy. Quoth one of the villains: "Your love destroyed your world, over and over again until even magic couldn't fix it..." To make matters worse, said villain is technically right.
  • ''The Taste of Pomegranates''. A Billy and Mandy fanfic.
    Mandy: "It doesn't matter either way, none of it really matters because I could not live without this feeling no matter how much it hurts. No matter how much I love it or hate it, I am in love with him and I cannot do anything about it."
  • For Good is made of this trope, be it in regards to family or romantic interests (or very good friends). The Ships 50 one-shots are especially Egregious.
    Erin: "Doggone it, why is this so hard? I don't want to be in love with the galaxy's Most Wanted!"
    Mira: "Hey, kiddo, nobody ever said love was easy. Like I said before, look at me and you think you've got issues?"
    Erin: "Yeah, I guess I wouldn't want to be in love with two guys at the same time."
  • Three Sherlock Holmes Fan Fic examples:
  • The My Little Pony: Friendship Is Magic fanfic A Delicate Balance is largely about the stress that romantic relationships can put on people, even when everyone involved is trying their hardest to make things work, even extending to characters who aren't directly involved in the romance.
  • Weightless has this trope as one of its main themes. God knows whether there will be more but currently, we have some of the following examples of how much love can hurt:
    • Loving someone but afraid to do so because you afraid that person will die like everyone who cared for you before (Shepard's case with Garrus and she had to break his heart once before managed to get over that to be with him).
    • Being coldly rejected by the person you love after you had given up everything for her. Have a fight with her only for her to die and you know that she did love you after all. Even worse if you get to know about her past and thought you scared her for trying to rush things physically as she was a raped victim. (Garrus's case with Shepard, resulted in 2 sleepless years drowning in guilt).
    • Unrequited love (Mierin to Garrus and, in the past, Shepard to Nihlus).
    • Your loved one was dead and you can't move on (Thane to his wife and Garrus to Shepard, though lucky for the latter that she came back).

    Film 
  • Davey Jones and Calypso's relationship in the Pirates of the Caribbean movies. Yeah, that ended well.
  • From the Hellboy movie art book: "When, in 1988, Liz Sherman joined the B.P.R.D., Hellboy fell in love. From then on, he knew the meaning of pain."
  • "The Hitchhikers Guide To The Galaxy has this to say on the subject of love: 'avoid, if at all possible.'"
  • The only woman James Bond ever married (Teresa "Tracy" Di Vincezo) was killed moments afterwards in a botched attempt to assassinate him. In later movies, it shows that even with all his flirting and skirt-chasing that he still mourns her.
  • Men In Black:
    J: You know what they say, it's better to have loved and lost than never to have loved at all.
    K: (looking horribly cold and restrained) Try it.
  • Love Actually. Daniel knows something has been bothering his stepson for a long time now, and he finally gets it out of him: he's in love with a classmate.
    Daniel: [laughing] Aren't you a bit young to be in love?
    Sam: No.
    Daniel: Oh. Right. Well, I'm a little relieved!
    Sam: Why?
    Daniel: Well, you know, I thought it might be something worse!
    Sam: Worse than the total agony of being in love?
    Daniel: ...No, you're right. Yeah, total agony.
  • Any of Wong Kar Wai 's films, especially In the Mood for Love and 2046.
  • Just use "Love Hurts" as a sub-title for Toy Story 2 and 3.
  • See: Five Hundred Days Of Summer .
  • The Sword in the Stone. Three words: heartbroken girl squirrel.
  • The whole point of Scott Pilgrim vs. The World ... in this case love multiplies itself by seven and storms into town on a homicidal rampage.
    • Poor Scott. As one tagline approximately reads: Scott Pilgrim has no trouble finding a girlfriend. It's getting rid of them that proves difficult.
    • But it turns out alright.
  • Beauty and the Beast: Goodness, the Beast's heartbreak after the uplifting ballroom scene is palpable. As he lets Belle go to her father at the risk of breaking the curse and spending his life with Belle he starts sobbing and finally breaks into a primal scream of despair as Belle gallops away.
  • The central theme of the Mexican film Amar Te Duele, which is about a rich girl and a poor boy who fall in love with each other, but society tries to keep them apart. It's even in the meaning of the title!

    Literature 
  • Animorphs: However much Jake and Cassie loved each other - and it was a lot - being together after the war wouldn't have been good for either of them. Despite that, being apart hurt them as well because of how much they cared about each other. Also, Tobias loved Rachel so much that her death destroyed him.
  • Medieval Chivalric Romance, anyone?
  • This is far and away one of the oldest, most universally recognized tropes in existence. A perfect example of it is found in the 12th century Persian epic, Layla and Majnun. Boy meets girl, boy loses girl, boy loses mind. It's not a cheerful tale.
  • Edgar Allan Poe was a very firm believer in this. He thought the best theme to write about was the death of a beautiful young woman, often leading to the protagonist's descent into madness.
    • Given the things that happened to women in his life, this isn't really surprising.
    • For those who don't know, tuberculosis killed every woman he lovednote . It killed his mother when he was young, two women that he was courting, and his wife. It's often speculated that the disease, which involves a great deal of blood loss, was the titular "Red Death" in his short story, "Masque of the Red Death".
  • Yuan, Lord of City Europe in David Wingrove's Chung Kuo series, falls for the wrong woman. Although the stage is set for serious tragedy, he manages to pull out of it.
  • The House of Night:
    • Zoey ends up falling for three guys simultaneously (ish). It ends badly when she thinks her own-age vampyre boyfriend Erik is dead, flees to the hot-but-older Loren for comfort, and ends up losing her virginity to him. Proving that Joss Whedon is not the only one who can be incredibly cruel to his characters, the following things happen in quick succession: it breaks her bond with her human boyfriend Heath, Erik walks in on her and Loren Kissing, and it turns out Loren was in cahoots with the villainess and only using Zoey. And then Loren is brutally murdered. Ouch. Poor Zoey. And it gets worse for her: the guy she displays a brief romantic interest in in the fourth book promptly dies, only to be resurrected as a bizarre zombie-vamp hybird controlled by her archnemisis. Zoey has a bit of a Cartwright Curse, it seems...
    • At the end of Burned between Stevie Rae and her consort Rephaim. The returning of Zoey's and Kalona's souls to their respective bodies serves to keep the two apart.
  • And Then There Were None features two victims who committed their crimes to keep their loved ones when it was those exact deeds that drove them away. General McArthur manipulated his wife's lover/his right hand into going in a suicide mission; Vera Claythorne caused the death of her pupil Cyril so his uncle/her lover could inherit the family fortune and drove said lover into alcoholism
  • In the Warrior Cats series, falling in love is likely to get you broken-hearted, insane, and/or killed. Bluestar wound up with all three because of her relationship with Oakheart.
    • Not entirely. Some lucky couples just end up getting their kits killed off. Yes, you heard me, they are the lucky ones.
  • Though The Engineer Trilogy as a whole plays this trope catastrophically straight, there is a scene lampshading it in the second. Miel Ducas, a powerful noble wounded in battle, hallucinates that he is having a conversation with Death. When Death points out that Ducas is not very grateful for having everything a man could ever want, Ducas replies that he is the poorest man in the world because no woman he ever loved returned his affection. Death explains that love is nothing more than a trick meant to override humans' free will in order to reproduce, and that Ducas might as well be upset that he never contracted diphtheria.
  • In Edgar Rice Burroughs's A Princess of Mars, John Carter realizes he fell in Love at First Sight with Dejah Thoris, but then manages to offend her.
    Yes, I was a fool, but I was in love, and though I was suffering the greatest misery I had ever known I would not have had it otherwise for all the riches of Barsoom. Such is love, and such are lovers wherever love is known.
  • Love doesn't hurt every character unlucky enough to experience it in the Indigo series...just most of them.
  • The Duel Of Sorcery series: Serroi and Tayyan are a couple at the beginning; then Serroi freaks out and effectively gets Tayyan killed. Rane and Merralis were a couple; Merralis contracted a terminal disease, and Rane is still mourning years later. Michael's boyfriend is beaten to death in front of him. There's more than a Ship Tease between Serroi and Hern (at least on Hern's end)...but then, Serroi gets turned into a tree in order to defeat Ser Noris. (She does get better in the follow-up trilogy, but Hern's long dead by then.)
  • Richard and Alec in Swordspoint and The Privilege of the Sword'', to the point where their relationship is such a mess that neither they nor the reader can figure it out.
  • A recurring theme in sonnets, especially those from the Renaissance.
  • Anna Karenina is 864 long, long pages of this trope.
  • The Great Gatsby could be argued to have love kills, and causes killing. It's arguable because actually being "in love" strongly tends to make the lovers happier - it's the fallout on everyone and everything else around them that actually brings the pain.
  • In L. Jagi Lamplighter's Prospero Lost, Ferdinard speaks eloquently of having suffered torments for the pure love of a chaste maiden.
  • Poor Gilbert Blythe lives this trope for over ten years; he falls in love with classmate Anne Shirley the day she smashed his slate over his head, but the reason for the smashing—him calling her "Carrots" and teasing her for her red hair makes her resent him for many years. When they finally become friends, Gilbert bides his time. He proposes, she turns him down. He proposes again (a couple years later), and she shoots him down again. It takes a near-death experience with typhoid fever for Gil to get his girl.
  • Many romantic relationships suffer from this in A Song of Ice and Fire as par it's Deconstructionalist nature, but no other character can claim that they've been through the worst of the Love Meat-Grinder than Petyr "Littlefinger" Baelish, who dared to fall in love with a girl above his social status. For his romantic idealism he was almost killed, possibly raped by the younger sister of the girl he loved, who then got pregnant and was tricked into aborting the child by her father, and sent packing from the home of his foster family, the place where he had grown up, back to his dreary homeland where no one knew him and he was mostly likely doomed to live out a lonely exile. The whole experience left him so severely unhinged that he became a Magnificent Bastard and started a continent-wide civil war to get back at his childhood crush.
  • Harry Dresden's romance life is an exercise in pain. Of the women he's been involved with or who he has strong feelings for/who have strong feelings for him, one gets turned into a vampire, has his child, and gets sacrificed, another is the copy of a Fallen Angel living in his head that kills herself to save him, and another is only in love with him because The Mole was mind-controlling her. Murphy still cares for him, but her reward for her affections is learning Harry is now dead. And then there's Molly, who goes from teenage crush on Harry to honestly being in love with him, but carrying all the baggage of his death as well and going almost completely nuts thanks to Black Magic and mental trauma.
  • The Picture of Dorian Gray features Basil who has to watch Dorian Gray, the love of his life and his greatest inspiration, descend deeper and deeper into corruption against his wishes and ultimately gets murdered by him. And then there's Sybill Vane who takes a fatal does of poison right after Dorian cruelly dumps her.
  • In C. S. Lewis's The Four Loves, he makes a point that there really is no escape outside of Heaven itself from this — except Hell.
  • Charlotte Bronte's protagonist Lucy Snowe in Villette is dripping with this. She even utters the line "My heart will break!"
  • Harry Potter and the Deathly Hallows: Poor, poor Snape. Spent the last years of his life trying to protect the son of the woman he loved — the same woman who rejected him for going with the Death Eaters (which was his fault entirely), and the same woman he all but killed. To make it worse, the guy she married was his worst enemy (who was reformed by that point). What makes it so painful is that their son is the spitting image of his father, yet his most distinguishing feature is his mother's eyes, reminding Snape of his failures and the fact that he Did Not Get the Girl.
  • In The Hunger Games Katniss isn't so much deciding between two boys (it's made clear halfway through the book that introduces the triangle which guy she's fallen in love with) as it is her deciding whether or not she dares to love. She's terrified of losing people close to her heart and her only real experience with genuine love is the love between her parents. They loved each other a lot but then her father died and left her mother a shell of a woman. Katniss is determined never to care that much about another person which is why she keeps resisting/ignoring her own feelings. Then comes the third book and Peeta, the guy she's fallen in love with, gets captured by the Capitol and is tortured, mind raped and turned into a weapon against her. Cue all that emotional pain she was trying to protect herself from.
  • The House of Night: Does it ever. Oh, does it ever. The end of "Chosen," anyone? Or "Tempted?" Though, considering that she was juggling three boyfriends at the time, the impact may have been lessened.
    • At the End of Burned between Stevie Rae and her consort Rephaim. Zoey and Kalona's souls return to their bodies, thus keeping the two apart.
  • Beren and Lúthien go through absolute hell for one another. Beren is a mortal Man, and Lúthien is the daughter of the Elven king Thingol and the Maia Melian. After eventually losing his father and all his kin fighting Morgoth, Beren wanders into Thingol's kingdom, where he has the gall to fall deeply in love with Lúthien. Thingol does not take this well, and sets him an Impossible Task: retrieve a silmaril from Morgoth's crown. Along the way, Beren and his companions are captured, tortured, and killed one-by-one by Sauron until Lúthien shows up and humiliates him. Together, Beren and Lúthien succeed in recovering one of the gems, but then Beren loses his hand (with the silmaril clutched inside it to the wolf Carcharoth. And then Beren dies helping slay the wolf to get it back. Then Lúthien dies of grief, and is faced with an eternity of being separated from her love because Men are not allowed to remain in Valinor upon death, while Elves are denied to pass wherever it is the souls of Men go. Her grief is so profound that her song of her fate manages to move the otherwise pitiless Mandos, who asks Manwë to intercede on their behalf, and the lovers are sent back to live again together. And this is pretty much the only happy story in The Silmarillion.
  • 19th century writer Higuchi Ichiyō's works are rife with this. Nearly all of her protagonists are young women, most are in love and none of them ever end up happy. If they aren't in love, they are married to a man they don't love and end up depressed, poor, and/or dead one way or another, with no way to escape their fate. She herself considered that in those times, women had very little power over their lives, so her writings are… not very optimistic overall. It doesn't help that she herself had been hurt by her unrequited love for her mentor in her first years of authorship.
  • In Edgar Rice Burroughs's A Princess Of Mars, Sola tells John Carter that because of this, and Hope Is Scary, she has wished to be like the other women of her race, without hope or love.

    Live Action TV 
  • In Smallville, Chloe Sullivan puts it best, and mildly.
    Clark, things always get messy when you start throwing around the Clark-Lana triangle, and I'm speaking from experience when I say the third point always hurts.
  • The new Battlestar Galactica series loves this:
    • Lee/Kara: They meet and fall in Love at First Sight - and nearly hook up - when she's already dating his baby brother, whose death she accidentally has a hand in. They become good friends and later survive the end of their homeworlds together, but the memory of the dead baby brother, and their guilt, keeps them apart and in Just Friends mode until they get together with other people, rather than face their feelings for each other. When Lee finally admits his love to Kara and gets her to do the same, she freaks out and marries someone else the next day, breaking his heart and leading to his own marriage to a woman he doesn't really love. After Kara survives a Cylon prison and some serious mindgames, they later reconcile and have an affair, but Kara won't get a divorce because of her religious beliefs, and when she finally unbends and considers the possibility, Lee is reluctant to leave his wife. And then Kara goes unhinged and dies, then returns and leads the Fleet to Earth. And just when it looks like it's all ok since they've found Earth, Lee doesn't care that Kara was really Dead All Along, and it looks like they'll finally get to be together, she tells him the fact that she was Dead All Along means she now has to disappear. As in, into thin air. Suffice it to say, Ron Moore is one of the few people who knows how to inflict more pain on a couple than Joss Whedon.
    • Adama/Roslin: They start out strongly disliking each other, move into a tenuous kind of peace with attraction, which gets shattered by the mutiny. Just as they fix that and get back to the tenuous attraction, she almost dies. Then, just as they fix that, SURPRISE CYLONS. Then once they kick the Cylons out, Adama gets hit with an attack of conscience, and then she's dying again, and then Earth, and then she dies.
    • Chief/Boomer.
  • John/Aeryn in Farscape. They make out. They fight alongside each other. They're tortured. They try to kill each other. They have sex. They die. (They get better.) They murder people to get back to each other. They fight. They make out. They blow up a bunch of bad guys. They have a kid.
    • D'Argo and Chiana are just as much fun!
  • Falling in love with the bad guy/girl is always a bad idea. Just ask Ace Lightning, who had to go and fall in love with the bad guy?s main hench-lady, who ended up sacrificing herself for him at the end of the series.
  • Every relationship in Supernatural. The Winchesters are crazy and clingy, Bobby had to kill his wife, Ellen lost her husband because John was an idiot, Sam's girlfriends tend to die horribly and Dean blurted out everything to his one-time girlfriend only to have her think that he was a lunatic and that she should break up with him.
  • In House, House's hopeless love for his ex Stacy causes the pain in his leg to increase. When Wilson points out that this is the reason House is having more pain, House wacks him with his cane and replies: "Awww, you miss Stacy too?" when Wilson keels over.
    • There is also a Season 1 episode titled "Love Hurts," in which Cameron blackmails House into going on a date with her and House responds by shooting her feelings for him down. Hard.
  • Kamen Rider, at least in the new generation, is as fond of this trope as it's fond of Anyone Can Die. On the rare occasions where a love interest to a major character is still alive by season's end, the relationship between them will likely have ended instead.
  • Highlander: According to Word of God, Duncan MacLeod has had "four great loves" in his life. All four are dead, and not of natural causes. In one flashback, a gypsy curses him, saying that he will "bury many women but marry none" - but his bad luck seemed to have started even before that..
  • Oz's Tobias Beecher loses his wife (she commits suicide), and later falls for Chris Keller, who it turns out was working for Schillinger, and they both subsequently break both his arms and legs. Busmalis even lampshades this after the incident. Though Keller arguably feels guilty afterwards, he spends the rest of the series trying to make it up to Beecher, both failing and succeeding at various points.
  • Friends: Ross and Rachel continually break each other's hearts with their Can't Stand Them, Can't Live Without Them relationship, Phoebe and David were separated by his job, Monica and Richard split up over wanting children and Chandler was devastated after Janice and later Kathy cheated on him and left. Averted with Monica and Chandler who were extremely happy after falling in love and had a healthy, fulfilling relationship. Also Phoebe and Mike eventually.
  • The Vampire Diaries: Primarily Stefan and Elena, but any couple who has been together fits.
    • Damon and Elena could fit too, although not as much as Stefan and Elena.
  • Love hurts quite a few people in Torchwood:
    • Ianto's attempt to save Lisa after she was partially roboticized causes nothing but grief.
    • Tosh is the show's poster child for Cartwright Curse.
    • In "Out of Time", Owen falls for an aviatrix from the 1950s. She feels the same way, but loves adventure more and risks another flight through the Rift. Owen has no idea where she ended up or if she survived.
    • "Children of Earth" - The only conceivable reason Ianto would've been in that room with the 4-5-6 is his absolute faith in and love for Jack, and then everyone Jack loves causes him terrible terrible pain in the end.
  • Doctor Who. All of the Doctor's companions "break his hearts".
    • And he broke Martha's. (And Jack's. And Sarah-Jane's.) That was exactly why she decided to stop traveling with him.
    • The Doctor and Rose are depicted as Starcrossed Lovers. Ultimately they are separated permanently, although at least they got to share a short goodbye quite a while after the fact. Subsequently a human version of the Doctor is created. Ten takes his human self to Rose's parallel universe to spend the rest of his human life with her. While for Rose this is a somewhat happy ending, the real Doctor looks heartbroken and lonely as he watches the two kiss each other, knowing she will be happy but he will go on alone without her. Rose gets to be with Ten, technically, but he will never get to be with her.
    • And later, the Doctor and River Song, on both sides. The day he meets her is the day she dies. And while he sees her again (their timelines running roughly in opposite directions), falls for her and marries her, it's all knowing how and when he's going to lose her. And from her perspective, she starts with a man who loves her enough to sacrifice his life for her, but with each consecutive meeting he knows - trusts, loves - her less and less, until their final meeting (or so they think) when he has no idea of who she is.
  • Sadly, this was the course that Robin Hood decided to take. Only two couples get a happy ending: Will Scarlett/Djaq and John/Beatrice (who were only guest stars). All the other couples: Robin/Marian, Guy/Marian, Robin/Isabella, Robin/Kate, Much/Kate, Allan/Djaq, John/Alice, and any slash pairing you can think of, ended badly. VERY badly. Though Robin/Marian did get a Together in Death scene.
  • Marcus over Ivanova in Babylon 5, going so far as to sacrifice himself to save her life, transferring his life energy to her as she lay fatally injured. She is devastated that he would do such a thing, regretting she never returned his affection
  • Naomi from Skins lives in blind terror of this trope, constantly running away from her love of Emily until she can't handle it any more; and when they eventually get together, she's still so scared of getting her heart broken that she tries to break Emily's first. It all ends with a Happily Ever After, though, after an Anguished Declaration of Love in the finale in which Naomi admits - and seemingly gets over - all her fears.
  • Joss Whedon must HATE happiness. Pick anything written by Whedon. The only exception is Simon and Kaylee, and that's just because they didn't get together until the end of the movie.
    • Buffy sleeps with Angel? He loses his soul and starts killing her friends, and then she has to send him to literal hell.
    • Willow and Oz are actually happy together? Oh no! We better make Oz go away to try and get rid of his wolf problem.
    • Giles has a nice grown-up relationship that's started to go somewhere? Guess who Angelus's next victim is?
    • Xander and Anya about to tie the knot? Xander gets a false vision of the future that destroys their relationship and sets Anya on the road to becoming a vengeance demon again.
    • Willow and Tara get back together? Oops, stray bullet on a physically impossible trajectory. Sorry, Tara.
    • Xander and Anya rekindle their love in the final season? Anya dies in the last episode.
    • Spike and Buffy patch things up in the last few episodes of Season 7? Time for some vampire flambé, everyone!
    • Then there's Joyce. In five years she dates a Stepford Smiler psycho robot and becomes a hormonal sullen teen along with Giles, to their mutual embarrassment - then she starts dating and enjoying it and BOOM, anyeurism.
    • In Season 5, Spike is tormented by his unrequited Foe Yay for the Slayer.
    Spike: "What the bleeding hell is WRONG with you bloody women?! What the hell does it take?! Why do you bitches torture me?!"
    Buffy: "Which question do you want me to answer first?"
    • Hooray! Angel and Cordy are going to have DINNER! Oh, ok Angel, we need to have your son lock you up underwater for the summer, and yeah, Cordelia, you're going up to watch over them for a while, and come back different.
    • Wesley and Fred couple up? "Hey, Fred, you want to die and come back as an ancient pure demon living in your body?" "Sure." "Sorry, Wes..."
    • The only happy marriage in the Firefly 'verse? "I am a leaf on the wind..."
    • Dollhouse. Topher and Bennett. So freaking adorab BOOM, HEADSHOT!
  • This could be the theme for Gossip Girl. If he's a nice guy, he'll sleep with someone else. If he's a redeemed jerk, turns out he's just a jerk. If he's your true love, he'll whore you out. If he seems perfect, he's sleeping with his stepmother or conning you out of your money or about to blackmail you into being his mistress. Love is pain, rich kids.
  • The titular character in Merlin (played by Sam Neill) goes through this several times in his relationship with Nimue. After he meets her for the first time, she is taken as a hostage by King Vortigern. When he gets around that, she is severely scarred by a dragon and withdraws to Avalon. When there is finally a good king on the throne and he thinks he can spend time with her, he learns of Mab's plot and has to rush back to Camelot to see Arthur. Then, years later, he thinks that they can finally, finally be together away from the rest of the world, but he leaves the place where they are staying, and it seals behind him, trapping her away forever. Unsurprisingly, the aged Merlin in the present says almost these exact words when telling his story. However, things turn out better at the very end.
    • His BBC counterpart wasn't much luckier. The only girl he ever loved, Freya, ended up being a monster who was killed by Arthur and died in Merlin's arms. Thanks to Merlin's love for her, she was able to come back as a spirit of the lake but they rarely get to see each other.
  • Art Kanji-Daemon is probably the Trope Codifier at how much love hurts him through all his life.
  • Bo and Lauren Any one who watches Lost Girl will know this couple is a good definition of this trope. Bo and Lauren want each other from the first time they meet, but they can't even kiss because if they do Bo will lose control and drain Lauren of her life force, Bo gains control and gets together with Lauren... but only for one night because Bo learns that Lauren was with her to distract long enough to stop Bo from killing someone (even though they would have gotten together on their own as Lauren explains) and Bo refuses to talk to Lauren for the next few episodes unless it is work related. Then in the season finale just before Bo goes to fight her mother Lauren gives her a kiss which Bo responds to.
    • Season 2 Bo and Lauren get closer again eventually shacking up in the 6th episode only for Lauren to return to the Ashes compound and Bo finds out that Lauren has a girlfriend in a Coma, they move past this a few eps later and kiss its all going well then Laurens girlfriend wakes up. this season is not even finished yet and there will be at least a 3rd season.
  • Oh, Call the Midwife! Dr Turner and Sister Bernadette spend an entire series in agony over their feelings for each other. On her part, she's a nun, and torn between her vows to God and the man she loves. On his part, he openly admits he would rather die than come between her and her God. As if that's not bad enough, oh guess what, she comes down with tuberculosis! Finally, in the last episode of the second series, they earn their happy ending when Bernadette, cured of her TB, decides that God is calling her to a different path. He asks her to marry him in very short order, and she says yes — but it is still bittersweet, as it means Bernadette has to leave the Order, which is all the family she has — most notably her beloved Parental Substitute Sister Julienne.
    • This applies to Sister Julienne as well in this storyline. When she finally no longer has to watch Bernadette going through her own personal hell, it's because she has to watch the young woman who is essentially her daughter leave the Order behind to marry the man she loves. The pain of letting her baby girl go is written all over Sister Julienne's face, giving a whole new meaning to the word bittersweet.
  • Like the book its based on, love in Game of Thrones usually spells tragedy. By the end of season 3...
    • Ned Stark dies far away from his wife Catelyn, and she is left grieving.
    • Daenerys Targaryen loses her husband Drogo despite her best efforts to save him. Her knight Ser Jorah Mormont is also in love with her, but she doesn't reciprocate.
    • Despite the homophobia of Westerosi society, Lord Renly Baratheon and Ser Loras Tyrell are in a loving, long-term relationship. Loras is heartbroken after Renly is murdered, and is consumed by a thirst for vengeance against the kinslaying Stannis Baratheon. Losing the love of his life is already incredibly painful enough as it is, but what makes Loras' suffering even worse is that he cannot openly express his grief as Renly was a man and a traitor to the crown. Joffrey has expressed a desire to execute all homosexuals, so Loras can't afford to let out any of his true feelings.
    • King Robb Stark and Talisa Maegyr have probably the happiest relationship on the show, but the political problems surrounding their marriage eventually lead to the Red Wedding, where the Freys deliberately murder Talisa (who was pregnant) in front of Robb, who has just enough time to crawl over to her corpse before being murdered as well.
    • Jon Snow and the wildling Ygritte are also quite happy, but the fact that Jon is The Mole in the Wildling ranks and they both know it grates on their relationship, until Jon is forced to show his true colours and runs away, leaving Ygritte despite her being willing to run away with him. She then shoots him three times with a bow to try and stop him.
    • Tyrion Lannister and Shae both love each other, but Tyrion can never let his father know of him and Shae's relationship since he will kill her, and he's too scared of his father to run away with her at her suggestion. His marriage to Sansa does not help matters.
  • White Collar: Neal goes through a lot because of his love for Kate - to start with, the four years he spent in prison were because he was desperate to find her and tell her that he loved her.

    Music 
  • The probable Trope Namer is an old country standard the Everly Brothers played. Famously, Nazareth gave it an epic metal treatment. From the sound of the singer's voice, love really hurts.
  • Incubus' aptly titled song "Love Hurts", although it could be considered a subversion; the chorus is, "Love hurts, but sometimes it's a good hurt and it feels like I'm alive".
  • Another subversion in "Hurt Me Bad (In a Real Good Way)" by Patty Loveless. The protagonist was hurt by love, but the pain set her free to find a better lover.
  • Sing with me...Love, love will tear us apart again...
  • "Please Don't Leave Me" by P!nk. WAY more so in the video of the song, where - when the guy tries to leave - she goes Stephen King on him.
    • Another P!nk song, "Try":
      "Where there is desire, their is gonna be a flame,
      Where there is a flame, someone's bound to get burned."
  • "... that's the pain that cuts a straight line down through the heart, we call it love ..." - Hedwig and the Angry Inch
  • Aerosmith, "Falling in Love (Is Hard On The Knees)".
  • "Love Stinks" by The J. Geils Band.
  • Baby, don't hurt me... no more... (Haddaway, best known as the theme song for the "Roxbury Guys" on Saturday Night Live.)
  • Leonard Cohen's famous "Hallelujah" is mostly about this, although the overall idea seems to be that it's worth it anyway as long as you know what to expect.
  • "Running Water" by DJ Shog featuring Irma Derby: "Love's like hot running water, once it runs through your fingers, painful in every way..."
  • "Love Bites" by Def Leppard. Describes love as an addiction.
  • Half the Rumours album by Fleetwood Mac are songs about how bitter falling out of love can be. "Never Going Back Again," "Go Your Own Way," and "Gold Dust Woman" in particular. The crowner is "The Chain," an anger-filled tune ("Damn your love, damn your lies") and is the only song on the album credited to all five members.
  • XTC's "I'm the Man Who Murdered Love" depicts the title character as a highly Sympathetic Murderer.
  • "To Love Somebody", originally by The Bee Gees.
  • "It's a Heartache", originally by Bonnie Tyler (and Juice Newton).
  • "Too Much Love Will Kill You" by Brian May.
  • "Fool for Your Loving" by Whitesnake.
  • "Only Love Can Hurt Like This" by Paloma Faith.
  • "Lollipop" by Mika.
    Mama told me what I should know:
    "Too much candy gonna rot your soul
    If she loves you, let her go
    'Cause love only gets you down"
  • "Adult Female: A Song" by Hank Green
    "Love is hard and love is messy and it can hurt worse than fire
    and sometimes it makes you want to tear down a building with your bare hands!"
  • The song "You Always Hurt The One You Love".
    "You always hurt the one you love/The one you shouldn't hurt at all"
  • "Terrible Thing" by Mayday Parade, which is song from the viewpoint of a father telling his son about how he met, fell in love with and married his mother. It than reveals the mother in fact died years ago and the father than tells his son that he should never fall in love and avoid anyone that tries to make him do so, because life can do terrible things.
  • "Breaking Us In Two" by Joe Jackson is about a couple who love each other but just can't make the relationship work long-term.

    Opera 
  • Pick an Opera, any opera.
    • Aida by Giuseppe Verdi is a good example. Aida, an Ethiopian princess in hiding, falls in love with and is loved by Radames, the general of the Egyptian army. Her mistress, the Pharaoh's daughter is her canny rival. After Radames saves her father, the king of Ethiopia, from certain death after being captured in battle, he brow beats her into fullfiling her "duty" as an Ethiopian to get Radames to reveal the Egyptian's troops' positions, sentencing him to death and dooming them to live apart. It's a "Happily Ever After" ending though; Aida sneaks into the tomb where Radames has been buried alive so they can slowly die together. So yes, the Deus Angst Machina is as integral a part of Opera as humor is to Comedy.

    Theater 
  • Romeo and Juliet and every imitator. Entire dissertations could be written on how both would have lived longer, happier lives if Romeo had decided to stay in and mope, Juliet had told him she wanted at least three dates before considering marriage, or the friar's advice to Juliet had been to take up her father's offer of being kicked out of the house so she could run away with Romeo easily, rather than telling her to fake her death.
  • The Phantom of the Opera is based around this trope with a Stalker with a Crush and Mad Artist with a Compelling Voice and a Torture Cellar (who often becomes the Draco in Leather Pants) proving that Love Makes You Evil and Stalking Is Love in a Love Triangle with a Damsel in Distress and her childhood sweetheart. He chooses in the end to let his beloved be happy, giving us a Bittersweet Ending.
  • Cyrano de Bergerac centers around a Love Triangle between three perfectly honorable, admirable people who all like and respect each other, two rivals who try as hard as they can to make the girl happy instead of fighting over her, and the original Playing Cyrano plot that isn't revealed until death has taken too many members out of the picture for anyone to be happy.
  • A fact of life for Fiyero, Elphaba AND Glinda in Wicked (and Boq and Nessarose for that matter). Elphaba even comments on it during Defying Gravity 'Well if that's love/it comes at much to high a cost'
  • City of Angels:
    Stone: Whoever said 'Time heals all wounds' never knew anyone like Bobbi.
  • Next To Normal:
    The price of love is loss
    But still we pay.
  • Company: The entire point of the song "Being Alive" and it's a good thing, because otherwise you're not really living.
    Somebody hold me too close, somebody hurt me too deep
    Somebody sit in my chair and ruin my sleep
    And make me aware of being alive, being alive
    Somebody need me too much, somebody know me too well
    Somebody pull me up short, and put me through hell
    And give me support for being alive, make me alive!
    Make me confused, mock me with praise
    Let me be used, vary my days
    But alone is alone, not alive!
    Somebody crowd me with love, somebody force me to care
    Somebody let me come through, I'll always be there
    As frightened as you to help us survive being alive
    Being alive, being alive, being alive!

    Video Games 
  • Max Payne 2
    This is love. When someone drags you from the wreckage when you have given in, ready to just lie there and die. This is love. When someone, no matter what the cost, shows you there is hope, a choice, that you can put down your gun. This is love. Love hurts. - Max's narration in a cutscene in Max Payne 2, just before his love interest is gunned down by the Big Bad because she refused to kill him. Depending on the difficulty you play on she gets better.
    • Max's first line in the game says it all: "They were all dead. Love kills."
  • Odin Sphere: The plot is full of this. Only a few characters actually get happy endings, assuming you didn't muck it up and get the bad ending, in which case it turns into a Kill 'em All.
    • The plot isn't just full of it. The plot exists because of it. The only things that don't seem to be linked to love is a war over control of a MacGuffin, and that was originally caused by this.
  • Neverwinter Nights: The unjustified execution of her fiancee led Aribeth de Tylmarande to insanity and an eventual Face-Heel Turn. The picture in the slideshow between chapters 1 and 2 with her crouched under the tree crying her eyes out sums this trope up very effectively.
  • Neverwinter Nights 2 has this for just about every relationship in the original campaign. Males who romanced Elanee learn she was killed saving them from a falling boulder. Females who romanced Casavir are told he was buried beneath tons of rock while helping everyone else escape. Females who did Bishop's semi-romance are betrayed, then later have to watch him die on the Wall of the Faithless. Guys who liked Shandra arrive just in time to watch her be killed by her grandfather. The only romance/potential romance that doesn't end in hurt is Neeshka's.
  • Persona 3's Yukari and Aigis. After the Protagonist dies, Yukari tries to move on, but is inevitably brought back to the dormitory where fond memories of our hero visit her. She's also jealous of Aigis, who inherited the Protagonist's power. Aigis is so saddened by the Protagonist's death, she wished she could return to being a mere machine, which gave birth to Metis, causing the events of The Answer.
    • Persona 4 could also be considered as having an example of this. Even if you have a love interest (or several) you will still leave any and all of your love interests behind as you go back to your actual home via train.
    • Persona 2: Eternal Punishment plot is started because Tatsuya, who was supposed to forget his memories of Maya from Innocent Sin, couldn't let her go and creates a Temporal Paradox because of it, allowing the Big Bad from the previous game to repeat the events. In the end, he gives up those memories and Maya can't be with him for fear of Tatsuya regaining his memories and dooming the world.
  • Metal Gear. There is maybe one successful romance in this series that does not put the characters and gamer through hell first. Meryl and Snake don't make it. Meryl winds up in a successful romance with Johnny, the series Butt Monkey. Raiden and Rose have so many issues that they deserve their own trope. They make it, which is more than most can claim, but they go through hell first. The Boss and The Sorrow were damned before the series started, with The Boss being forced to shoot her own lover. And he let her. Naked Snake and EVA failed. Fanon aside, EVA doesn't get Snake, even though she loves him and bore his sons (against his will). And Otacon? He might as well put a bullet in the head of every woman he shows affection for and save time. Ground Zeroes adds Chico and Paz. Chico, who is in love with Paz, attempts to rescue her, only to be captured and tortured physically, emotionally, and psychologically. Once it finally looks like they might make it out alive, Paz reveals that she has a second bomb inside of her and sacrifices herself to save the MSF survivors, dying right before Chico's eyes. Yes, this game is very cynical, whatever gave you that idea?
    • Is it any wonder Kojima averted this hard in Zone of the Enders? There, only one "pair" ends badly (in this world, at least).
    • Kojima played this straight again in Castlevania: Lords of Shadow, damning Gabriel and Marie right before the beginning of the story.
  • Planescape: Torment: It's not the only thing that hurts. But boy does it hurt. See also: Deionarra.
  • Good God, Utawarerumono with Hakuoro and... well, everyone. Eruruw is apparently physically unable to confess until her contract with him is dissolved. He doesn't pick up on Karura's rather blatant overtures. Touka just weirds him out. Which is understandable. Urtoriy can't be in a relationship with anyone apparently and most certainly not the divinity of her religion. Oh, and the ill girl kind of gets what she wanted except it was mostly out of pity/platonic love, and she died after giving birth anyway. For the hurting part on his side, losing Mutsumi hurt so much that his identity split into two godlike beings that cause chaos, wars and destruction every couple years. There's an implication at the end that Hakuoro comes back, and he did essentially admit he loves Eruruw. Oh, and Kamua probably didn't love him so she's okay.
  • Final Fantasy IV has Kain and his unrequited love for Rosa. All Love Is Unrequited hurts by itself, but then you factor in how he lost her to his best friend Cecil, and it gets real painful, especially since he clearly wants them to be happy, but is still full of jealousy and sorrow.
  • Final Fantasy VI has this with Locke and Rachel, where Rachel accidentaly loses her memory and her parents blame Locke for the whole mess, he blames himself becauses Rachel in her memory stricken form tells Locke to leave because her parents are yelling at Locke, afterwards, he learned that at the time of the villages demise, she regained her memory, and called for him... Then, he asked a doctor to preserve her body, while he searches for a way to save her, while still blaming himself for everything... Damn....
  • In Final Fantasy IX, Sir Fratley, the love of Freya's life leaves on a journey of epic training. When she doesn't hear of him for some time, she embarks on the world to find him. During the events of the game, she eventually runs into him but he is suffering from amnesia and doesn't remember her. Ouch.
    • It's even on her quote in the game's manual. Quite a Player Punch when you find out what it means:
      Despair. To be forgotten is worse than death.
    • In the game's ending, his memory never returns, but he falls in love with Freya again, anyway. Awww.
  • In Super Robot Wars Alpha Gaiden, resident Badass Samurai Sanger Zonvolt gets this. The woman he deeply cared for (not to the point of open romance, but deep, deep loyalty and affection) was turned into a monster he and the Preventers had to kill, and the poor bastard not only gets to watch her die, but his only comfort in the end of the game is cry over her grave. Alpha 2 gives him a Roaring Rampageof Revenge when Kukuru tries to off Sophia Nate (woman he cares for). He's a little better off in the OG Timeline, only now it's Wodan Ymir who gets screwed, which (long story) is the same thing.
  • Mega Man X4 has finally included the option of playing as Ascended Extra and major fan-favorite Zero, along with his own story. The bad part? In Zero's story, he has to fight and kill Iris, his own girlfriend, who wants to seek revenge on Zero for killing her brother. The narm that came with the game's horrible voice acting ruined one of the truly heartwrenching moments in the series. (The original Japanese voice acting did a much better job in powering the said Tear Jerker moment.)
    • She doesn't even want to kill him, instead attacking him because she can't forgive him for killing her brother, but can't bring herself to move on from his death. Essentially, the poor girl is so shattered that she's choosing Suicide by Cop, and it breaks Zero as well as herself.
  • Oichi in Sengoku Basara is this in spades. Thanks to her love with Nagamasa and her care about her brother, who happens to be Obviously Evil, she's in for tons and tons of tragedy, starting from seeing her lover die in front of her, then delusionally thinking that Nagamasa wants everyone dead, then she kills off all her family and then gets herself killed.
    • The fourth game introduces Shibata Katsuie, whose unrequited love for Oichi is why he's such a downer, though he shows tinges of Entitled to Have You as well. In one of Oichi's story routes, he goes so far as to kills Nagamasa, which simply drives Oichi into a murderous rage.
  • In Breath of Fire IV, this was essentially what fuels the Hex Cannon/Carronade. The closer the sacrifice was to the intended target, the stronger the hex will be. This was what broke Fou-lu and cause him to go Kill 'em All near the end.
    • Cray spent much of the game searching for Princess Elina, Nina's sister and his love interest. When they found her, Elina was turned into an artificial Endless, in order to exploits her love as an limitless fuel for the Carronade. Cray ends her suffering with the Dragon Slayer.
  • In Brutal Legend, a female voice cites a sad poem about a girl whose heart is broken and is compelled to drown in the Sea of Black Tears. It's actually talking about The Ophelia of the cast, who is named, well...Ophelia.
  • Got played straight and exaggerated in King's Quest IV: The Perils Of Rosella. Edgar, Lolotte's homely adopted-by-kidnapping "son" Edgar has developed a fondness for Rosella, and pulls a Heel-Face Turn to free her from a prison. Rosella escapes, takes Cupid's love arrows and shoots Lolotte. The evil fairy is so overcome with sheer pain she shrieks "It HURTS!" before falling over dead. Edgar is rewarded for his heroism by Genesta returning him to what's later revealed to be his true form, and he asks Rosella to stay with him. Rosella has to refuse his offer and get back to Daventry, presumably leaving him alone and somewhat heartbroken. At least, until the seventh game...
  • Fallen London. Common parlance in the game is to never, ever fall in love. Particularly, it's important to never, ever ask the Bazaar for help in situations involving love. Results tend towards horrific transformations, resulting in the Cantigaster and the current state of most of the Empress's children.

    Visual Novels 
  • Fate/stay night: The ending of the Fate route exhibits this to a certain extent. Saber dies, and although Shirou manages to get over the loss remarkably well, he says that he will always remember that he loved her.
    • The Heaven's Feel Normal End, however, takes this trope Up to Eleven. Shirou dies in order to protect Sakura, and she moves into his house and spends the rest of her life mourning him and waiting for him to return to her (he never does...).
  • Love, be it platonic, familiar, or romantic, in the When They Cry franchise tends to end in tragedy.
  • Yasu (A.K.A. Shannon, Beatrice, and Kanon) from Umineko: When They Cry, as quoted on the quotes page. Rosa, too. And Kinzo. And maybe also Erika.

    Web Comics 
  • MAG ISA - The message is, "Love hurts...but you need it."
  • In Sluggy Freelance: Torg's crush on Zoe earns him quite a bit of this as the series goes on, best summed up in the Mind Screw arc "Wayang Kulit".
    • He gets off easy compared to Oasis, who has died multiple times because of her unrequited love for Torg.
  • While Lia and Fiona, from YU+ME: dream , don't have any easy time at first, this is nothing compared to when the major Drama Bomb hits. This seems to be intentional, as the author/artist explains here.
  • "What can hurt more than a concrete enema?"
  • Digger: Ed's backstory. Dear God, Ed's backstory. And through it all he never, ever stopped loving. Oh, Ed.
  • No Rest for the Wicked
    • The Beast is crazily obsessed with Beauty and rages, insane with jealousy, when she's late returning.
    • Prince Ricardo, being Minor Flaw Major Overreaction embodied, goes around breaking hearts as quickly as he can rescue princesses — and is none too happy himself.
    • Claire and King Gareth appear to have been Happily Married, but he went to war. Now they are separated; Claire won't explain what happened to her child, and refuses to meet him because she feels too guilty; and Gareth signed a peace treaty because he was too heartbroken over the news of his wife.
  • Zoophobia: Damian's obsession with Kayla always leads to this.
  • In Sinfest,
  • In Doc Rat, Doc observes that both love and martial arts hurt.
  • In Homestuck, due to the complicated social dynamics and age of the protagonists, this trope gets used a lot.
    • In particular, with Karkat Vantas, who despite being adept at helping other people sort out their romantic issues, is constantly tortured by his inability to sort out his own, in particular, with Terezi, his love interest. Being a self-loathing Jerkass Woobie doesn't help this.
    • Eridan Ampora also invokes this, as he desperately hits on everyone but ends up with nothing to show for it, usually to comedic effect. This is justified because he is a douchebag, but later becomes a lot less funny when it becomes a factor in him murdering two of his friends.
    • Nepeta Leijon also qualifies. She wants nothing more than for Karkat to just notice her, but she doesn't think that anything will ever happen. And then she gets horrifyingly butchered by an Ax-Crazy Gamzee.
    • Davesprite and Jade breaking up is an interesting example of this; Jade initially seems largely unaffected by the whole thing despite the fact that Davesprite's the one who broke up with her. It's Davesprite himself and, oddly enough, John who seem to be upset about the whole thing (Davesprite, being Dave, isn't exactly emotional about it but doesn't appear to be all too happy about it either; with John it's implied to be a Big Brother Instinct scenario). When Jade is under mind control, her confrontation with Dave has her vent some of her feelings about the relationship, shouting that he broke her heart.

    Web Original 
  • In The Antithesis, love is a perpetual curse on most characters, whose personalities and ideas of affection become tainted through life experiences pertaining to love. Alezair's love for Leid repeatedly condemns him to fits of rage, insanity and substance abuse, and at one point his devotion for her nearly ends his existence entirely.
  • Comes up a lot in Survival of the Fittest because Anyone Can Die (and usually will), the most prominent examples include:
    • Bryan Calvert goes through the death of Tori Johnson, whom he'd been protecting for almost the entire game.
    • Adam Dodd's girlfriend Amanda Jones is killed in his absence, setting him off on a path of revenge going after her murderer.
    • Ricky Callahan similarly safeguards his girlfriend Whitney Acosta for most of v2. When Calvert accidentally kills her, Ricky commits suicide.
    • Sean O'Cann, after recently coming out of the closet and engaging in a thoroughly romantic relationship, gets this treatment, with his boyfriend Andy Walker biting the dust not long after the game began. Cruelly, they'd met each other prior to this and become separated, leading to Andy's death.
  • Billy (Doctor Horrible) spends the entirety of Dr. Horrible's Sing-Along Blog painfully infatuated with Penny, only for his Arch nemesis Captain Hammer to accidentally kill her while trying to kill Doctor Horrible with his own Death Ray. This was after Captain Hammer dated Penny just to screw with Billy.
  • In Happy Tree Friends, every single episode featuring a romantic relationship ends in tears (and often, blood as well). The only characters who have survived an episode unharmed and together are Cuddles and Giggles in I Nub You, and they weren't the stars of that episode.
  • In Noob, Arthéon has a girlfriend during the entire fourth season. Long story short, Noob is a five-season webseries.

    Western Animation 
  • Teen Titans:
    • Just when things were looking up for Beast Boy in the last season, culminating in him successfully leading a team of C-list teen heroes against the arc's Big Bad, the series gave him a Downer Ending/No Ending with the return of either a look-alike or an amnesiac Terra, his morally conflicted season 2 flame.
    • According to the spin-off comic, Terra is faking amnesia.
    • That whole thing with Malchior betraying Raven in "Spellbound" after she fell in love with him.
  • True for both The Hero and Worthy Opponent on Avatar: The Last Airbender: Aang is told he will have to let go of his love for Katara to ever master the Avatar State, and after becoming disillusioned with his life in the Fire Nation, the one thing Zuko has to leave behind that he still cares about is his New Old Flame Mai. See, they're Not So Different. They get them in the end, though.
    • And then there's Sokka who had his first love perform a Heroic Sacrifice and become the new moon spirit.
  • In its sequel Legend Of Korra: The Love Dodecahedron in Book 1 is suitably messy for a teenage love triangle. Korra goes on a date with Bolin after being rejected by Mako whose dating Asami. Korra then kisses Mako the next day who kisses her back, only for Bolin to see, breaking his heart. Mako regrets the kiss but Korra getting kidnapped causes a love epiphany which makes Asami suspicious. After she finds out Mako has been hiding the kiss, she breaks up with him. Korra and Mako become an Official Couple.
    • In Book 2 Korra and Mako breaks up over the their jobs. Asami and Mako kiss in the heat of the moment so it seems like they might get back together. Korra lost her memories and therefore doesn't remember that they broke up. So Mako doesn't tell her and tries to act like it didn't happen,something that everyone and Asami disapprove. Eventually Korra regains her memories and they break up again. Bolin meanwhile gets into a relationship with a Yandere Eska and has to run away from it.
  • At Chowder episode At Your Service, Panini threw some tacks to the running Tall Legged Chowder, and when he is trapped in the middle of the tacks, he stated that Love Hurts.
  • Taken to its logical extreme in an episode of The Grim Adventures of Billy & Mandy. When Pud'n wishes on a Jackass Genie skull for a pet bunny that will love him, he gets a literal interpretation of this trope.
    "Sometimes love hurts, Pud'n, and I love you a lot."
    "I forgive you, Pud'n. I forgive you because I love you! And I love you... to death."
  • The KaBlam! episode "A Nut in Every Bite" had Henry falling for Mr. Stockdale's visiting granddaughter, Dawn, but he only seemed to be able to charm her by hurting himself. (It's probably also worth noting that June wasn't exactly happy with this.) After Dawn leaves:
    June: I'm sorry she had to leave, Henbud.
    Henry: I'm not. She was killing me!
  • Total Drama.
    • Trent develops a relationship with Gwen, only for Heather to screw it over through a Gambit Roulette and send him packing after he and Gwen manage to patch things up. Come Total Drama Action, he gets jealous over her getting closer to Duncan, which leads to his obsession with the number nine and throwing challenges so that Gwen's team would win, which leads to her dumping him so the competition would be fairer. Ouch.
      • It doesn't help that the nine obsession has nothing to do with their relationship, instead having to do with an incident involving one of the wheels of a ten-wheel toy train given to him by his late grandfather falling off.
    • Tyler and Lindsay fall in love, only for Lindsay to forget who Tyler is until Season 3. And two episodes after that, she's eliminated.
    • Alejandro confesses his love for Heather in the final episode of Season 3, only for her to knee him in the kiwis, throw him down the volcano, and grab the million-dollar briefcase instead.
    • Courtney becomes an Official Couple with Duncan in Season 1. They dance a very painful Masochism Tango throughout all of Season 2, Duncan is the cause of her downfall close to the end, and the relationship dissolves for good in Season 3 after Duncan cheats on her with Gwen and remains in a relationship with her. She then falls for Alejandro, who is just using her.
    • Cody really likes Gwen, but she doesn't like him back. And meanwhile, Sierra really, really likes him, but he doesn't like her back. Ow.
    • Harold harbors yet more one-sided love for LeShawna.
    • Owen broke up with Izzy, but later regrets it deeply. "Oh, my Izzy, why'd I ever let you go?"
    • Finally, Gwen. Poor, poor Gwen. In Season 1, she sees Heather kissing Trent as part of the aforementioned Gambit Roulette, with expected results. After she dumps Trent in Season 2, she loses all of her popularity in-universe due to some behind-the-scenes manipulation by Justin. It doesn't get any better in Season 3: Duncan finally kisses her...while he's still with Courtney. Cue everyone being mad at them, but Gwen getting the worse load of blame and finally being eliminated just two episodes after the incident. Jesus Christ.
  • Superjail!: The Warden's one-sided love for Alice is this.
  • In Green Lantern: The Animated Series Aya discovers this when Razer claims he can never love her because she is Just a Machine. Most of her considerable processing power is spent replaying the moment over and over again. It gets so bad that she shuts down her emotions. Things get worse from there.
  • The main character's rejection drama in the first episode of City Hunters is symbolized multiple times, and causes the listless attitude that inspires Dr. Lynch to help him out.
  • While more a Puppy Love example, there's the infamous crush Ralph Wiggum developed on Lisa when she was the only one to give him a Valentine.
    Krusty: Is this your girlfriend, Ralph?
    Ralph: Yes, she is. I love Lisa Simpson, and when I grow up I'm going to marry her.
    Lisa: Noooooooooooooooooooooooo! Now you listen to me! I don't like you, I never liked you, and the only reason I gave you that stupid valentine is because nobody else would!
    (Back at home)
    Bart: Watch this, Lis. You can actually pinpoint the second when his heart rips in half. (Slo-Mos the video) Aaaand... now!

    Real Life 
  • Linguistic examples:
    • In Swedish, Norwegian and Danish the word "gift" (pronounced "yift") means both "married" and "poison", one wonders if this was made so on purpose...
    • In Japanese, "Ai" means love but it can also mean "grief/sorrow" when written differently.
    • The Japanese got it from Chinese, where the exact same thing happens: save for the tones, the words for the two concepts are homophones.
    • In Russian, "брак" ("brak") means, among other things, both "marriage" and "spoilage/defect."
    • In English:
      • Apparently, "to wed" (Or some form of marriage word) comes from the same roots as "gamble".
      • The word "passion" itself ultimately descends from the Greek pathos, "suffering."
    • In Spanish, "Cazar" is "to hunt" and "Casar" is "to wed." In Latin America and some parts of Spain, the pronunciation is identical. The word "esposa", which means wife, also means handcuff. Same goes for the plural "esposas".
    • In Portuguese, "Caçar" is "to hunt" and "Casar" is "to wed."note , so it's as above.
    • In Danish:
      • The words for heart (hjerte) and for pain (smerte) rhymes, which is sometimes used as a proverb.
      • Again with "lidenskab" meaning "passion" and "lide" meaning "to suffer", though unlike German, the connection is for some reason rarely made, possibly because the word "lidenskab" is barely being used among most people in everyday life. In an inversion, "(at kunne) lide" can also mean "to like".
    • In German the word "Leidenschaft" which means "passion" belongs to the root word "leid" which means "suffering".
  • As if we need to say it: Truth in Television.