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  • Advice and Trust:
    • Gendo is a bastard because he had always been frightened of other people. Yui was the only person he ever opened up to. When he lost her he became a broken, pathetic shell of a man, too afraid to love and relate to other people and utterly obsessed with saving her. All of it is explored in chapter 8.
    • When Shinji and Asuka got together they were happy because they were not alone anymore... so that when one of them was in danger or they were forcibly separated they were terrified of being alone again.
    • Shinji and Asuka helped Rei to stop being a puppet and connect with other people. She bonded with them to the point she loves them both and it hurts her being unable to be with them because they don't love her that way and she does not want to disrupt their bond either.
    • Shinji and Asuka helped Touji and Hikari to get together. When Hikari got absorbed into Unit 03 Touji spent several days depressed, lonely, afraid and worried, not knowing what had happened to her.
  • Applejack's Love provides a zigzagged example: Fluttershy and Big Mac get together without much trouble. Applejack and Dashie on the other hand…
  • In 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 Child of Love:
    • Shinji fell in with Asuka. When she treated him rudely to push him away or claimed wanting nothing with him, not even after getting pregnant with his child, or got hurt, it hurt him. Especially if she got hurt.
    • Asuka did not want love anyone because she had been hurt by people she loved. She did not want to admit she loved Shinji because she was afraid of getting hurt again. Later she opened up to him. However he broke up with her for a while because he thought he was not strong enough to protect her and their child. As a result she got hurt and furious because she had trusted her and he left her.
    • Both of them argued the subject here:
      Asuka:"I-I mean...you're speaking with confidence...you're so shy, usually. I think I'm like this because I trust you and I feel that I can put my trust in you. You're like a confidante."
      Shinji:"I...it's the same for me. We've got a lot in common, don't we?"
      Asuka:"You try to avoid pain by running away from people. I try to avoid pain by driving them away. But in the end, we just hurt ourselves more. Aren't we pathetic, Shin-chan?"
      It sounds more like a statement than a question. Shinji can't help but be surprised by this sudden truth coming from the mouth of the girl he normally knew to try to avoid it. Somehow, the suicide attempt, as bad as it was, seemed to have turned Asuka into a more mature person.
      Shinji:"You're right, Asuka-chan. It's kind of like...we're hiding ourselves from the pain behind a shield."
      Asuka:"But we just feel more and more pain."
      Shinji (nodding):"Yeah...you're right, we are pathetic."
    • And later Misato offered her input:
      Misato:"You're not alone, Asuka...I'm here, we're all here for you. You know that...and, yes, this is love. With all the happiness and sadness it can bring to you. Love is like a double-edged sword. One day it can make you the happiest person on earth, and the next day, it can make you cry like you never did before."
  • Children of an Elder God:
    • Rei fell for Shinji as soon as she met him, but Shinji was deeply in love with Asuka and he regarded Rei as a good friend. Worse still, one of the Eldritch Abominations absorbed by Rei forced her to hurt Asuka physically and mentally. Rei had no chance to talk Asuka into sharing Shinji or having a three-ways relationship after that, so she resigned to having an unrequited love.
    • In the Final Battle, Rei sacrificed herself to save everyone. Even though they won and survived the war, her teammates couldn't fully celebrate their victory because they loved her and missed her.
  • A Crown of Stars: Shinji and Asuka have hurt each other… and still love each other.
    • Asuka does not want to love anyone because she is deadly frightened of getting hurt again. Daniel tells her that’s tantamount to refusing eating because you are frightened of getting poisoned.
  • 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.
  • Evangelion 303: Asuka was the first and only woman Shinji had loved. Before meeting her he had no drive to live on. Then they got together, were happy for a while... and Asuka's experimental jet fighter crashed down. She was in a coma for several months. Shinji refused leaving her side during that whole time. When she woke up she was a nearly completely different, ever-angry person. For several months Shinji had to see her self-destroying gradually as he put up with her abuse, having no idea of how helping her. Later she got better after trying to kill herself and then running away and she admitted it hurt her remembering how she treated him during that time.
  • 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."
  • Hetalia: Axis Powers fanfic Gankona, Unnachgiebig, Unità: Japan felt immense pain after Italy seemingly chose Germany over him. Italy denied his feelings for both Germany and Japan because he thought they could do better than him and would eventually get over him.
  • In Ghosts of Evangelion Shinji and Asuka hurt each other many times but they stay together and keep trying to make their relationship working because they care for each other.
  • The Golds: Due to her feelings for Jefferson, Katja nearly throws herself over the town-line just so she could forget him, feeling like she is trapped with all of her regrets and shame in the town. Rumpelstiltskin of all people had to be the one to talk her out of it.
  • Marisalon from A Green Sun Illuminates the Void is a big believer in this (as such is innate to the psychological make up of a Exalted-style demon); eventually this comes out in a rather telling statement when she and Louise argue briefly on the subject.
    Marisalon: There is no love without pain.
  • In Hellsister Trilogy, Supergirl falls hard for fellow Legionnaire Dev-Em. In Superman of 2499: The Great Confrontation, set five hundred years after her time, her descendant Kath learns that relationship left Kara heart-broken and burned-out.
    The diaries were frustratingly incomplete. Gaps, missing pages ... Of the love there was little doubt. With First-Husband Dev-Em there could be no mistake about that at all. Love and passion for him poured from the pages of Kara's diary like a river.
    Dev... Dev... Dev... Kara's diaries were full of his smiles, the sound of his voice calling her name. The feel of his body and the labyrinth of his mind and heart. No, all this was plain for any and all to read. What was less clear was what happened to him.
    Something had sent a grieving Kara Zor-El fleeing back to Rokyn, wounded in spirit and bleeding from the only place she was truly vulnerable: her heart. Something terrible had happened. And yet the diaries did not name the cause. Whether this was because there were parts of it missing ... or because Kara Zor-El could not bring herself to speak of it was difficult to know. The only thing that was sure was that, beyond a certain point, the name of Dev-Em was never spoken.
  • HERZ: Shinji and Asuka truly love each other but they have hurt a lot throughout the years. Shinji's obliviousness deepened Asuka's emotional and psychological scars, his actions in “End of Evangelion” cost her life -albeit temporarily- and made her feeling defiled and an ugly, unlovable monster. On the other hand her posterior abuse, fuelled by her resentment and self-loathing, drove Shinji to the edge.
  • 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.
  • In Neon Genesis Evangelion: Genocide:
    • Shinji and Asuka love each other, and they've hurt each other a lot.
    • Yui's actions also hurt and traumatized her son Shinji, but even so he loves his mother.
      Shinji thought about that, and about what Asuka said regarding them never losing their mothers, and how when she made him talk about her he had felt so dejected until she took his hand and shared her own pain with him. And then he realized that even though he badly missed her, he was also glad he could remember her. Her memory remained strong in him because he loved her, and the day he stopped missing her was the day he stopped loving her.
  • The Night Unfurls: One of the reasons why Kyril is unwilling to engage in courtship and romance is because he believes love only ends in pain for him and others. He once considered himself a good man and loved another during the Night of the Hunt, but it went awry. Kyril admits that had he were a normal guy instead of a Shell-Shocked Veteran Hunter of Monsters who is secretly a Humanoid Abomination, maybe he would consider. The story presents a benign deconstruction of this trope by showing how it needn't be as drama-laden or heart-wrenching as it is often assumed to be. Kyril doesn't deny feeling sad about his loss, despite being The Stoic, but he doesn't dwell on it. He decides not to find a romantic partner or fall for anyone precisely because he wants to prevent pain and further loss. The idea that "love is pain" is a signal. A signal that helps him make a pragmatic decision for the good of himself and others, not to set himself up for anguish and frustration. Furthermore, even though he believes this trope to be true, Kyril is still capable of opening up to his doll confidant and platonic friend, expressing pride to his apprentices, and providing consolation to his unwanted suitors. All in all, it's okay to feel that Love Hurts, because a) you can just choose not to fall in love, and b) it doesn't mean you are incapable of caring, helping, or feeling happy about others.
  • Once More with Feeling:
    • Shinji fell in love with Asuka. When he saw that she had gotten killed by the MP-Evas it shattered his sanity to pieces. Even though he returned to the past to Set Right What Once Went Wrong it haunts him knowing he did nothing as she was getting chopped into pieces and eaten alive.
    • After meeting Shinji Asuka starts to connect with him deeply, and it scares her because she is afraid that she will get hurt if she falls in love with him.
  • The One I Love Is...:
    • Shinji had been alone since he was a kid and he was resigned to it. Then he met Asuka and Rei and he fell for them. However Rei blew herself up to stop Armisael and Asuka ran away and slit her wrists because she thought she had lost him. Shinji was alone again for a while and he felt loneliness was unbearable now.
    • Asuka fell for Shinji and it hurt her knowing he had feelings not only for her but also for Rei. After her Mind Rape she felt he was the only thing she had left. Thinking she had lost him too was the final blow to her mental stability. She ran away and attempted to kill herself.
  • One Year Rise takes the relationship between Yu and Yukiko the hardest, particularly considering that Yu, who'd hooked up with Yukiko in early July 2011 (after Rise was rescued but before she joined), had been taken the entire time Rise had been flirting with him. It also doesn't help that her being an Idol Singer essentially precludes her chances of getting together with Yu. Thankfully, Chie, who also had a crush on Yu and struggled with being jealous of Yukiko, helps Rise work through her feelings.
  • In Carol Danvers fanfiction A Prize for Three Empires, Kree soldier Iva Kann sees no point in getting emotionally attached to someone and being hurt. Still Carol argues that loving someone is worth of the risk of a heartbreak.
    Iva Kann: You Earthers. Your emotions as corrupted as that of Captain Mar-Vell. You think by a heart-bonding with another individual, you can make them stay. How idiotic. Best to have one’s way with them, and let them go.
    Warbird: We don’t think that, Iva. Sure, our loved ones are going to go. Everybody goes, you know that. But the love-bond is so important to us that we risk the pain to forge it. Like the pain you have to go through in a battle to win it. It’s like that, Iva. Very much like that.
  • Rivals Series: Viktor Nikiforov's Brutal Honesty bites him in the ass when he unintentionally insults a twelve-year-old Yuuri Katsuki, who is absolutely crushed by the thoughtless words of his childhood idol. Yuuri then devotes the next ten years of his life to beating Viktor and crushing everything he ever achieved, partly out of contempt, and partly out of his underlying desire for Viktor to acknowledge him. All of this becomes an issue when Viktor falls in love with Yuuri, which complicates their relationship on so many levels and hurts them both.
  • The Saga of the Last Two Saiyans:
    • Goku develops romantic feelings for Vegeta after Vegeta kisses him while drunk. He believes his feelings will never be returned and tries to bury them. Whis tries to help Goku get over Vegeta with mental training, but it doesn't work.
    • When Goku visits Chi-Chi in Heaven, she tells him it's sad that he and Vegeta will never get to find love again due to the soul-bond. This causes Goku to believe he's caused Vegeta eternal suffering.
    • Eventually Goku believes it would be better for him to permanently fuse with Vegeta. He thinks this would make Vegeta happy and make it so he wouldn't have to live with his unrequited feelings.
  • Scar Tissue: Shinji and Asuka loved each other but had hurt each other badly. After Third Impact Asuka's mind was broken and her temper out of control, and Shinji blamed himself for his actions and inactions. He put up with Asuka's abuse for several months because he loved her, he could not live without her and he thought he deserved her punishment. On ther other hand Asuka beat him and she always felt sick with herself afterwards. After a while she managed to stop abusing him but she still hated herself for hurting the only person she loved.
  • The Second Try: In chapter 4 "Love" Shinji told Asuka that Instrumentality had taught him that you can not to experience love and happines without taking the risk to feel pain and loneliness too. Both of them choose taking a chance and get together and later have a child. Later they got flung back to the past without Aki where they had to cope with their daughter's disappearance and the fear to lose each other again during the Angel War. When Shinji got swallowed by Leliel and later absorbed into Unit 01 Asuka was freaking out, feeling alone and frightened of losing him again. Later Shinji believed the MP-Evas had killed Asuka again and he could not stand the pain. He very nearly set Third Impact again.
  • Stars Above: Hoo boy. To quote 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 Tamers Forever Series uses love as a surgical scalpel to subject the characters to unimaginable suffering.
  • Thousand Shinji:
    • When Shinji arrived on Tokyo-3 he slowly got granted that he had always wished: a family -Misato and Rei-, a lover -Asuka-, friends... When they got hurt he got hurt. And then he made someone else hurt. Later Misato and Asuka got killed and their deaths broke him down completely.
    • Shinji taught Rei a new world of emotions and feelings. However he loved her like a sister. His brotherly love was insufficient to her, and it hurt her seeing him with Asuka and resented Asuka for making him happy. Her inability to deal with her unrequited feelings and her accumulated jealousy and resentment led him to make very stupid things she ended up regretting.
    • When they got together Asuka became fully dependent on Shinji. He made him happy took the pain way only for being there. She loved him but she was frightened of losing him and getting hurt again. When he got absorbed into Unit 01 she fell completely apart. She was hurt, lonely, depressed, snappy... and homicidally furious at everyone.
  • 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.
  • ''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."
  • Three Sherlock Holmes fanfic examples:
  • 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 she 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 rape 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).
  • White Rain: Lucia van Alstyne realizes that she loved the father of her children, Itachi Uchiha, after a therapy session/interrogation with Ibiki. It hurts, because by the time of this realization, Itachi has been dead for years, and is not coming back. The fact that her son is the spitting image of his father most definitely does not help at all.
  • Walking in Circles: At first, Solas doesn’t dare to reveal his feeling to Evelyn as he thinks it as a betrayal to his people to fall in love with a shemlen, not to mention he’s also afraid of Evelyn’s reaction if she knows who he is and what he’s planning. Only when she becomes Tranquil that he finds to courage to confess but it’s already too late, and he spends the next two years regretting everything while trying to keep her safe. As he put it, having her by his side during those years was both an agony and a relief.
    • Evelyn, meanwhile, thinks that she’d never be able to leave her Circle while Solas values freedom more than anything so she can’t reveal her love as it would tie him down.
    • Kinnaird is in love with Fitz but they were only together for a short while before broke up due to Fitz constantly trying to escape and Kinnaird wanting to keep his sister safe by staying obedient.
  • The Flower Princess and the Alchemist: Ed and Orihime seemed to go through copious amounts of this before and during their relationship.
  • they'll name a city after us Apollo has been in the receiving end of this trope for the entirety of his immortal life. Either by his lovers dying on him or via them betraying him. Once he falls in love with Percy Jackson he takes no chances, going for Abduction Is Love and trapping the demigod in a Gilded Cage in Delos.
  • kuch adhura sa jo tha (poora ho jayega): Sam tells Kamala that even though love is fickle and someone you love can totally rip you apart if they choose to, true love is worth all the pain and dangers that come with it.
    Sam: You can never truly love someone until you aren’t afraid of getting your heart broken. When you love someone, you give them power over your heart. You can never be completely sure if someone won’t break your heart, yet you love them anyway. Because real, true love is worth it.

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