Love is a beautiful thing, but there are a lot of stumbling blocks that can get in the way of someone experiencing it. Unfortunately, the possibility of winding up with a broken heart is all too real, and for those who have had their hearts broken, the pain can be extreme. In fact, the emotional hurt that comes from being dumped can be literally painful, and even traumatic. So, it stands to reason that any compassionate person would take steps to ensure that, even if they have to break up with someone, they do it gently and respectfully, minimizing the pain.
And then there's this person. Rather than break hearts through ignorance, circumstance, or even by mistake, these characters do it willfully and deliberately, leading their victims along and allowing them to get attached, before shattering their heart with little to no remorse.
They may be the Alpha Bitch, stringing unlucky nerds along for her own cruel amusement and taking advantage of their crushes on her. They may be a serial womanizer, looking for sex, and attracting so many partners they couldn't care less about the ones who've developed feelings for them. They may be a typical Jerkass with a Lack of Empathy, someone who cares only about themselves, or even a Narcissist or Sociopath, up to being a Sadist, in the most extreme cases. In many cases, they're manipulative enough to be a Manipulative Bastard, intentionally fooling their victim. Regardless of who they are, though, they have one thing in common: they find a romantic partner, trick them into thinking the romance is real or allowing them to think it is, and then carelessly toss them aside, intentionally or willingly hurting them in the process. Characters who do this are also more likely to pull other cruel tricks on their "lover", such as breaking up with them over email, cheating casually and often, or even committing acts of Domestic Abuse.
As such, it's no surprise the character who does this is usually the bad guy. Even if their victim is being targeted out of revenge, often for having broken another person's heart or because the heartbreaker themselves has had their heart broken in the past, this will be portrayed as a morally ambiguous act at best, something too cruel for even the resident asshole to deserve. Even if the person has a conscience and feels guilty over it, they'll still go through with it, despite knowing it's wrong. Of course, if the entire relationship is done for the purpose of breaking someone's heart, there's a high chance of the manipulator Becoming the Mask; in those cases, dual-heartbreak is on the horizon.
A similar trope is Relationship Sabotage; where both tropes can result in someone having a broken heart, Relationship Sabotage involves an outsider messing with the relationship, which could result in both partners getting hurt. Also compare this to Commitment Issues, where someone may go into a relationship with no intention to stay in it but aren't doing it maliciously. Other tropes to compare are Operation: Jealousy, Shock Value Relationship, Fake Relationship, I Was Only Pretending To Like You, and Hope Crusher. This may result in It Meant Something to Me, Ladykiller in Love or Did You Actually Believe...?, and is often committed by a Handsome Lech, The Casanova, The Vamp, or the Troll. This is often a Kick the Dog moment, or if done particularly cruelly, an out-and-out crossing of the Moral Event Horizon. Not to be confused with Break His Heart to Save Him, which is where a character only cruelly dumps someone out of desire to protect them.
- Sarazanmai has Villain of the Week Kiis Motoclay, a pretty boy fishmonger who becomes a local Casanova in Asakusa. Before the heroes properly get to fight him, we learn that he was arrested on suspicion of marrying women and then driving them to suicide to collect marriage fraud reimbursement. His monster form reflects this, as he turns girls into wedding dolls that kiss him and then turn into dead fish for his collection.
- It's heavily implied in Kaguya-sama: Love Is War that the only reason Osaragi went out with Kazeno was so he wouldn't get in the way of Ishigami asking out Tsubame. Once that goal was achieved she promptly dumped him without any consideration for his feelings.
- In Seven Soldiers, former Kid Hero Sally Sonic was seduced by Vitaman, an older superhero who learned that she was the daughter of the judge who had put him and his brother away. In order to avenge himself, he got Sally hooked on drugs and turned her into a criminal. Later, after getting free of him, Sally got revenge on all men by seducing married men and utterly ruining their lives before dumping them, which is how she became the archnemesis of Bulleteer, whose husband was her final victim, who died when he tried to give himself superpowers in the deluded belief that it would get Sally back.
- Frozen: Prince Hans pretended loving Anna just to usurp the Arendellian throne. With Anna dying from the icy heart curse unintentionally placed by Elsa, he even rubs it in her face. It briefly leaves her broken, but Anna eventually realizes that there are still others (Kristoff and Olaf) who care about her. In fact, Hans invokes the Villain with Good Publicity trope to make his coup more stable and subverts the classical Disney Prince Charming trope by using his fake charm to manipulate others, notably Anna, whom he duped into thinking he was her One True Love for most of the movie. He even fools the audience the entire time into thinking he's a nice man. The spoilered character has been confirmed by the creators to be a "frozen-hearted" sociopath.
- In Scooby-Doo! and the Monster of Mexico, Luis spends the entire time pining after his fiance Charlene, who he loves dearly. At the end, however, we learn that Charlene not only never loved him, but was one half of the Chupacabra plot, planning to force Luis and his brother to sell their land so she and her real love, Mr. Smiley, could reap the benefits after she dumped Luis. She tells him all of this to his face.
- Alex of Heartbreaker is hired by parents wanting him to seduce daughters who fell in love with men her families don't want.
- This is the main premise of In the Company of Men, in which Chad and Howard aim to seduce a co-worker to deliberately break her heart as revenge against the female gender after they'd been dumped by their exes. Then it turns out that Chad's girlfriend never actually dumped him — he did it purely For the Evulz.
- In John Tucker Must Die, the titular character had cheated on three girls at the same time, and the protagonist, Kate, was the one who caught him. In an attempt to get revenge on him, the others convince Kate to break his heart and teach him a lesson. Kate goes into the relationship with the full intention of humiliating him later but starts to genuinely care about him, and questions the morality of what she's doing. Of course, she still goes through with it.
- Arrows of the Queen mentions a cruel noblewoman who pretended to love Dirk so as to get close to his handsome best friend. When said friend rejected her attempt to cheat on Dirk, she went and tore into the latter, telling him to kill himself. Unfortunately, since the woman technically didn't break any laws, all the authorities could do was ban her from the Collegium.
- In the Betsy-Tacy book, Betsy in Spite of Herself, Julia considers doing this to Mr. Gaston as revenge for mistreating her little sister Betsy in class, after she discovers he has a crush on her. Betsy is glad when Julia decides not to go through with it.
- Great Expectations: Estella Havisham is main character Pip's love interest, whom he thinks he's being groomed to wed because he's under the mistaken belief that her adopted mother, Miss Havisham, is his secret benefactor helping to advance him in society. In reality, Miss Havisham has been grooming Estella to be her weapon to take revenge on men in general by making them fall in love with her then breaking their hearts. Estella herself claims she has no real affections for anyone due to her training.
- In The Heroes of Olympus, one rite of passage for the daughters of Aphrodite involves making a boy fall in love with you, then breaking his heart. Piper puts a stop to this after she takes over.
- Søren Kierkegaard has a character in his work ''Either/Or' known as "Johannes the Seducer", a man who seduces a woman named Cordelia so he could encourage her to break the relationship. The editor, Victor Eremita; and the author of the "Either" section, "A"; deem him so morally bankrupt that they take time to disavow the Seducer.
- Mansfield Park: Henry Crawford happily flirts with any single lady of his acquaintance while he never means to be serious and never means to get married. His sister Mary mentions a string of her intimate friends whose hearts Henry broke. He "courts" sisters Maria and Julia Bertram both at once, but soon zooms in on Maria because she is already engaged and so it's a bigger challenge, and he apparently enjoys messing with people's emotions. Later when Fanny Price is the only unmarried young woman in Mansfield, he specifically says to Mary that he decided to make her fall in love with him and "make a hole in her heart". She proves immune to his charm because she remembers how he treated her cousins Maria and Julia, and the cad falls in love with Fanny for real.
- Tales from the Mos Eisley Cantina: High-functioning Sociopath Feltipern Trevagg sees a space bimbo he wishes to seduce so he can break her heart/hearts. Little does he know that in banging her he is offering himself up as a ritual sacrifice through disembowelment.
- In Wayside School Gets a Little Stranger, Wendy Nogard, after getting dumped by her fiancé Xavier for having a third ear, uses her third ear's mind-reading powers to get men to fall in love with her and then break their hearts. She plans to do the same thing to Louis after learning he has a crush on her until feeling the pure love of a baby melts away the bitterness in her heart.
- House of Anubis:
- When Jerome cheated on both Mara and Willow, Mara was so furious, she talked Joy into pretending to date him; the plan being that if Jerome falls in love with Joy, she breaks his heart in front of the entire school. Of course, Jerome genuinely starts to fall for her, and she begins to feel guilty over it, especially since she starts to like him back. She still goes through with it to make Mara happy, and both of them end up heartbroken, with Jerome being utterly devastated that she was tricking him.
- After Alfie became a Sinner, and lost his conscience, he stopped caring about Willow. When she turned to him for support over something Joy and Mara were upset over, he just insulted her, broke up with her, and immediately started flirting with Joy and Mara as Willow stood there, stunned and sobbing. With this being his first act as a Sinner, it was a huge Kick the Dog moment, establishing him as cruel and willing to hurt the people he used to love.
- Downplayed in Scream Queens (2015). The reason Pete hates Chanel so much is that, when he was still a freshman, he had a crush on her. She agreed to go out with him, opened up about an embarrassing fetish of hers, which he agreed to partake in... only for it to turn out it was all staged. She laughed at him for being so gullible, her friends had seen the entire thing, and he left, utterly humiliated and hurt by the experience.
- Victorious: In "Beggin' On Your Knees", Tori starts dating an attractive boy named Ryder Daniels, from her music class. She's completely smitten, but Trina warns her not to trust him because he's dated several girls before her. Robbie eventually discovers that not only has Ryder dated a lot of people, but that his modus operandi is to date talented girls so he can get a good grade, and then dump them when he no longer needs them. This is what he was planning to do to Tori after their graded duet and to make it worse, he'd played with her heart prior by temporarily dumping her for looking through his text messages.
- How I Met Your Mother: Barney Stinson tries to have sex with as many women as possible and he often breaks hearts in the process. Sometimes the girl he picks up knows very well it's a one-night-stand, but he very often manipulates his dates and specifically targets gullible women. He makes them believe he wants a committed relationship, takes them to other people's flats and talks about how he wants to settle down, and he mentions he proposed to women to have "I-can't-believe-you-just-proposed-to-me" sex, etc.
- It's Always Sunny in Philadelphia: Dennis Reynolds deliberately sets out to do this to as many women as possible and devises an entire system to do so, which he calls the D.E.N.N.I.S. system: Demonstrate value, Engage physically, Nurture dependence, Neglect emotionally, Inspire hope, Separate entirely.
- The Tanya Tucker song "I'll Come Back as Another Woman" has the narrator vowing this as revenge against a guy who did this to her.
I'll come back as another woman
One with all the secrets to your heart
I'll come back as another woman
I'll be the one you burn for
That you reach for in the dark
I'll be the one who breaks your devil heart
- "Destroyer" by Saint Motel, where the singer tells of the woman he fell in love with despite everyone warning him not to, and how she unabashedly left him in ruins:
I don't break hearts
No, that's not me
I don't break hearts
I destroy them
- "How to Be a Heartbreaker" by Marina Diamandis is sung from the perspective of a heart breaker, and gives some slight insight into how people like this think and act, implying that people who enjoy toying with other people's emotions do so because they have been hurt themselves in the past.
Girls, we do, whatever it will take
'Cause girls don't want
We don't want our hearts to break, in two
So it's better to be fake
Can't risk losing in love again, babe
- Dwight Yoakam's "Intentional Heartache" is about a woman named Connie who, when catching her man in the act, retaliates by wrecking his car and spray-painting his belongings.
- Fire Emblem: Three Houses has Sylvain. While a Handsome Lech on the surface, he actually hates it when girls make passes at him, as he assumes they're after his Crest instead of loving him as a person. This personal frustration from being born with a Crest inspires him to flirt with girls before unceremoniously dumping them within a few days as a form of revenge, though he does admit to feeling bad about what he does, and post-timeskip he's mostly grown out of this.
- Sly Cooper: Thieves in Time: Penelope pretended to love Bentley because he had the skills she needed to make a fortune and Take Over the World, and didn't think of him as anything but a disposable tool. Although when she did break his heart, it was by accident; Penelope had no idea that Bentley was watching her from the rafters when she smugly gloated about her goals, and showed no care when he confronted her for this, as if Penelope had been plotting to dump Bentley the moment he outlived his usefulness. It backfires, and Bentley angrily dumps Penelope for her cruelty, healing his heart in the process.
- Valkyria Chronicles has two examples.
- Maxmillian in the first game is this towards his right-hand woman, Selvaria. The moment he figured out that she was in love with him, he became a Master of the Mixed Message and used emotional manipulation to ensure she remained in his service. By denying her affection if she fails in her endeavours, and only giving it to her if she succeeds, he convinced her that she needed to perform her role as his general to her utmost in order to earn his love. After she is defeated by Squad 7 at Naggiar, she gives Maxmillian an Anguished Declaration of Love and begs him for another chance... he responds to her pure love and tireless devotion by coldly ordering her to be a suicide bomber in a last-ditch attempt to win the war that he started.
- The sequel has a more light-hearted version in the form of Sofia. She hates men since a crush asked her out on what was actually a Prank Date. She gets her comeuppance on men by leading them on and then breaking their hearts. Only Idiot Hero Avan manages to actually get under her skin and cause her to have genuine affection, which results in her dropping this behavior.
- In Double Homework, Tamara acts this way toward Dennis. She dates him mainly out of revenge on the protagonist, knowing full well that she wouldnt even try to make it work.
- Totally Spies!: Eugene Snit from the Season 2 episode "Matchmaker", who, having had his heart broken by his girlfriend on Valentine's Day a year previously, vowed to do the same to every single girl in the Beverly Hills High. Using stolen technology to posse as numerous different individuals and admirers, he seduced every single girl, then planned to stand them all up at the big Valentine's Day dance.