"Do what? Do I ice her? Do I marry her? Which one of these?"The Professional Killer is as deadly as he is serious about his job, "Nothing Personal, it's just business" is their favorite quip for a reason. He can spend months infiltrating a target's life and winning their confidence without hesitating to pull the trigger once the order comes. Of course, there's always that one target... not The One That Got Away, but the one that got into their heart. Love has a way of sniping even the coldest heart, and against all sanity and better judgement the hitman grows a heart. Maybe in the process of casing the target he (usually a he) may discover she's just an Innocent Bystander who saw too much, and his Badass Creed emphatically says to Never Hurt an Innocent. Then again, it may just be plain old messy love sprouting as some ineffable quality of the target strikes a long dormant chord in his heart. Maybe they just have really good sex. At first he'll make increasingly implausible excuses to his superiors at the assassin's guild to justify not killing his Love Interest, even protecting her from rival hitmen until ultimately they decide he's gone rogue and put a Contract on the Hitman. Interestingly, whenever this happens the hitman was usually going to be betrayed anyway either by the client or his organization, and the defection quite literally saves his life. The former target Love Interest will of course be really freaked out once she finds out the man she loves wanted to kill her not days ago, but usually rolls with it surprisingly well and trusts the hitman with her life implicitly. A weird sort of Stockholm Syndrome can be said to affect both: though their love is genuine, the situation is eerily similar. The old assassin's maxim "Don't get involved with the mark, it can get messy" is putting it mildly. Another Moral Dilemma facing the Hitman with a Heart is just what exactly to do vis-a-vis his former colleagues and innocents. Now that he's essentially done a Gender Flipped High-Heel–Face Turn into at least being an Anti-Hero, he can't just kill anyone he pleases. The Love Interest usually insists on holding him to a more moral standard, and only killing those who attack them or betrayed them.
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Anime and Manga
- Rethink your definition of "love", and you have Seishirou Sakurazuka from Tokyo Babylon and X/1999.
- Crying Freeman has Emu Hino, who saw Yoh Hinomura for the first time right after he murdered one of his targets. She was singled out for death... but she and Yoh fell in love and ran away together.
- Rolo in Code Geass develops a strong, genuine affection for Lelouch Lamperouge while posing as his younger brother to monitor him and saves his ass (which kills him).
- Ironically played with in Rurouni Kenshin. Assassin Kenshin and Tomoe fall in love with each other. However, the mark is Kenshin, not Tomoe, who is a spy for Kenshin's enemies, who intended to invoke this trope on purpose in order to use her as a hostage and lure Kenshin into a trap. Poor Tomoe tried to help Kenshin break through, and got killed (and by a blinded Kenshin, himself) for her trouble.
- In Risky Safety, the oni woman Kade was sent to assassinate one of the Momotaro men. He sensed her attack, blocked it...and then they saw each others' faces and fell in love. Much to their respective armies' dismay.
- One episode of Noir has Kirika befriending a target. She kills him anyway.
- El Cazador de la Bruja has an episode where Nadie and Elis meet a husband and wife running a restaurant. Turns out that the husband was originally hired to kill the woman, but fell in love with and married her instead.
- In Attack on Titan, Ymir hints that she befriended Krista with the sole intention of using her to convince the enemy to pardon her past crimes. Instead, this is what happens.
- In Nisekoi, the hitwoman Tsugumi develops feelings for Raku.
- City Hunter's character Mick Angel plays with this. Whenever the mark has a girlfriend of woman, he seduces her before completing the job, allegedly to make her suffer less (given the first we see of him is seducing a woman who is about to marry and whose fiancee is not his mark, this claim of his is somewhat doubtful). Then Union Teope sets him on Ryo, so he goes to seduce Kaori... Only to actually fall for her.
- Akuma no Riddle is a manga series about a class in which twelve assassins target a normal girl named Haru Ichinose. One of the assassins, Tokaku Azuma, falls for Haru and eventually decides to protect her from the other assassins.
- In To Love-Ru, the Living Weapon Golden Darkness ends up falling in love with her target Yuuki Rito. So much so that her "Darkness" mode wants to kill him so that he can live on forever in her heart.
- Also, the reason why she was contracted to kill him was to capture his fiancée, who is the CURRENT HEIR TO THE GALAXY. She ends up loyal and completely devoted to Lala.
- Tsukiyama is believed to develop feelings towards Kaneki in Tokyo Ghoul besides just seeing him as a meal.
- The necromancer in the first issue of Death Vigil genuinely fell in love with Clara at some point before he tried to sacrifice her to evil entities that want to eat reality.
- Probably the case with Yith, a snake-woman assassin hired to kill Curt Connors in the mini-series Spider-Man, Quality of Life. Yith had been paid by Corrupt Corporate Executive Clifton Arliss to get rid of Connors (who had discovered the dangerous health risks of his agricultural projects), but started feeling sympathy for him after hearing about the death of his wife. Eventually, during a fight between Spider-Man and Curt (who had become the Lizard) she did little but watch, and after passing up several easy shots at Curt, she pointed her gun at her employer and asked if he'd ever been in love before - then let him have it. (And then left without an explanation.)
- The somewhat, um, 'infamous' Warhammer 40,000: Dawn of War fanfiction "Love Can Bloom".
- Suzaku is a time traveler in My Mirror, Sword and Shield who only made himself close to Lelouch to ensure that his timeline isn’t wiped out by Lelouch dying too early or too late with plans to assassinate him himself as insurance. Suzaku ends up falling in love with him and begins to lose his nerve. He ends up faking Lelouch’s assassination and saves him by taking him to Suzaku’s future.
- Barbara Stanwyck does this in both The Lady Eve (where she's a cruise ship card shark falling in love with mark Henry Fonda) and Ball of Fire (where she's a stripper pretending to be in love with Gary Cooper so she can hide out from the cops, until she isn't pretending).
- Played with in Grosse Pointe Blank. The hitman is actually in love with his mark's daughter.
- Ćon Flux. It's a Justified Trope because they were lovers in a past life.
- Mr. & Mrs. Smith zigzags this. It's inverted in the beginning, when the two titular characters, neither of them knowing the other is a secret agent, fall in love and only get the order to kill each other when they've already been married for a few years. At that point their marriage was failing, however, and for a while they really try to kill each other... only to fall in love again, playing the trope straight.
- The movie Portrait of a Hitman. Not exactly 'falling in love with' but he can't pull the trigger on her.
- Undercover Brother. After falling in love with the title character, Penelope Snow (AKA White She Devil) can't go through with killing him.
- In The Whole Nine Yards, Jill Saint-Claire is hired to kill Nicholas "Oz" Oseransky by Nick's wife. But as her plan to get close to Nick (in order to more easily kill him, of course) proceeds, she finds she likes him too much to actually go through with the hit. It's even discussed in a conversation between Jill and fellow hit-man Jimmy "The Tulip" Tudesky:
Jimmy: "Oz, you are the most chivalrous guy I've ever met."
Jill: "Do you see why I couldn't kill him?"
Jimmy: "Yeah... I love him!"
- When Jimmy is supposed to kill Oz, he can't do it either.
- In fact, he ends up killing a friend, another hitman, instead, although there are pragmatic reasons for that as well (he knew Frankie would betray him eventually).
- During the above conversation about "loving" Oz, Jimmy does mention a previous time he fell for a mark. He told the mark he was there to kill him. Unlike Oz, this one tried to kill Jimmy in response. Jimmy found he didn't love him anymore.
- When Jimmy is supposed to kill Oz, he can't do it either.
- Wild Target: The killer is initially unable due to chance to kill his target, but later he is bemused by her eccentricities and eventually falls in love and marries her.
- This occurs off-camera in the movie Conspiracy Theory
- Subverted in Red Eye. Jackson Rippner develops a Villainous Crush on his target Lisa but he continues to go through with his mission.
- The parents' backstory in Spy Kids. They were secret agents working for different countries, were assigned to "take each other out," fell in love, got married, settled down, had kids, got kidnapped by a Depraved Kids' Show Host...You know, normal parent stuff.
- In Hercules, Hades ordered Meg to spy on Hercules to find out if he had a weakness. Meg and Hercules end up falling in love. Hades is initially furious, but then he gets wise to how he can take advantage this...
Meg: Besides, O Oneness, you can't beat him. He has no weaknesses! He's gonna...
- A bromance version occurs between Dave Skylark and Kim Jong-un in The Interview. Of course, Kim is just "honeydicking" Dave.
- The tale of Amor and Psyche, a story-within-a-story in the Metamorphoses by the Roman author Apuleius (2nd century A.D.), makes this trope Older Than Feudalism at least.
- Cawti from Steven Brust's Dragaera series was a highly skilled assassin, who was hired to kill Vlad Taltos (she succeeded, but he got better) and ended up marrying him.
- Dianora from Tigana plans her entire life out to kill Brandin for destroying her hometown and removing its name from people's minds, but when she finally manages to make it to his harem, and into his bed, she can't go through with it because she loves him desperately.
- The heroine of The Assassins of Tamurin series ends up falling in love with the prince she was sent to kill and renouncing the teachings of her Evil Cult.
- In Corrupting Dr Nice by John Kessel, grifter Genevieve falls in love with Owen, the wealthy but naive biologist whose pet dinosaur she and her father are trying to steal. Subverted in that he rejects her when he finds out what her profession is. As revenge, she woos him all over again under a false identity, then does everything in her power to hurt him after they're married. They eventually reconcile, though.
- In Death series: Averted. Memory In Death has Eve Dallas finding out thing Bobby Lombard married Marnie Ralston, who was pretending to be Zannah. Marnie only married him because she was trying to hurt his mother Trudy Lombard as well as steal her stuff. Then she impulsively killed Trudy, tried to cover it up, as well as attempting to kill Bobbie for kicks. Eve has to tell Bobbie about all this, and warns him that she will use this trope to manipulate him. Naturally, he is unable or unwilling to believe what she's telling him.
- A minor example from the BattleTech novel Close Quarters: Protagonist Cassie Suthorn isn't exactly sent to kill the Honorable Percival Fillington, Earl of Hachiman. Merely gather incriminating evidence of a conspiracy against her employer in which he is involved, which could easily lead to his death if it fell into the wrong hands. In the course of her mission, she doesn't precisely fall in love with him, either, but he does inadvertantly get past her own defenses enough for her to realize that he's after all an imperfect but fairly decent man whom the other sides in said conspiracy are using mainly as a highly-placed convenient pawn and with whom she could be friends if it wasn't for his being on the other side (and for her own deep-seated psychological issues). It motivates her enough that after her recovery she argues with her employer in favor of sparing him, and since her "impertinence" amuses Chandrasekhar Kurita, Percy does in fact get to live and even keep his position as though nothing happened. Until the next book, anyway...
- Logan's Run: At first, Logan was just using Jessica to lead him to Sanctuary, so he could destroy it and become the greatest Sandman who ever lived. But her bravery and will to live make an impression and she ends up as his Morality Chain instead.
- In Scarlet, Wolf's purpose was to gain the titular character's trust, coax secrets out of her, and then hand her over to be tortured and killed. Thanks to The Power of Love, he manages to overcome his More Than Mind Control to save her.
- In Grave Mercy, Ismae is ordered to accompany Viscount Gavriel Duval to court in order to uncover plots against the Duchess and kill the perpetrators. The Abbess, Ismae's superior, is convinced that Duval is a traitor; she expects Ismae to find evidence of his guilt and promptly kill him. Eventually, it becomes clear to Ismae that Duval's true allegiance is to the Duchess. He honestly has nothing but her best interests at heart, and is indeed the more or less the only person who does. However, due to misinformation, the Abbess finally flat-out orders Ismae to kill Duval. Ismae refuses to do it, mostly because Duval is innocent, but the fact that she's fallen in love with him certainly influences her decision to disobey.
- In Cloud Of Swallows, Heiko (the most beautiful woman in Japan) was hired to seduce and assassinate Genji. She fell in love with him, and he wasn't fooled in the least. Her boss lied to her. He wanted her to fall in love with him, and vice versa, to make his revenge nastier. It worked!
- In the Discworld novel Mort, the human apprentice Mort, covering for Death, is sent on an assignment to claim the soul of the princess Keli. Poised with the sword (for royalty), he decides he cannot do it, as she is too young and attractive. And the consequences of Death declining to take just one soul reverberate around the Discworld...
- Robert Sheckley seemed to like the trope, as he has several rewritings of a story based on it. It is set Next Sunday A.D., when anyone can join the so-called Hunt. Five times you have to become the Hunter, hunt down and kill the Victim, and five times you are the Victim and have to try and kill your Hunter. Sheckley flipped genders of his characters and changed the ending several times, but the ultimate idea is the same: the Hunter falling in love with the Victim and refusing to kill him/her.
- In Die Alchimistin, Gillian, a professional assassin, is assigned to kill his master's Arch-Enemy and the latter's young daughter Aura. The first murder goes off like a charm, but then Gillian meets Aura, and the two are instantly drawn to each other. Despite attempting to kill her, Gillian can't bring himself to finish the deed and lets her go, turning against his master. Later he and Aura become lovers.
- Cole (Belthazar) from Charmed was originally sent to kill Phoebe (and her sisters) but ends up falling in love with her.
- Alec from Dark Angel fell in love with the daughter of the mark. The mark was later expanded to include her.
- On General Hospital, female FBI agents can't seem to help but fall for the mobsters they're trying to send to prison. Sonny Corinthos actually slept with two such agents (one died and the other was Reassigned to Antarctica), and a third lost her job after falling for Spinelli.
- This is the origin story for Christopher Chance, the Human Target, including the Innocent Bystander who saw too much, former colleagues, and the Contract on the Hitman. Unfortunately, it ends badly for the love interest, who dies before the end of the episode.
- An episode of the show, however, has this trope go somewhat better for another spy/assassin, who upon being ordered to kill her husband of three years (who she originally married as part of a long con), instead plans to fake both their deaths. (Then the husband hires Chance to protect him from her, not knowing anything about said plan.)
- River Song from Steven Moffat's run of Doctor Who: she fell in love with the Doctor, despite having been kidnapped as an infant, raised and trained specifically to destroy him. In their first meeting from her perspective, she came very close to killing him permanently, but ended up sacrificing her remaining regenerations to save him. In the end, her "owners" resort to just grabbing her and sticking her in an automated suit. And she still finds a way not to shoot him.
Tasha Lem: They engineered a psychopath to kill you.The Doctor: Totally married her. I'd never have made it here alive without River Song.
- Buffy the Vampire Slayer:
- Spike, who shows up in Sunnydale to kill Buffy, ends up falling in love with her.
- Anya originally appears with the intention of cursing Xander who cheated on Cordelia.
- On Leverage, during "The Lonely Hearts Job" a con artist falls in love with her rich husband and ends up disappearing to try to protect him, kicking off the episode.
- On Castle, a con artist is murdered because he falls in love with his rich fiance and his partner in the con kills him to try to earn the money.
- In a CSI episode, the victim's wife and secretary are revealed to have been planning on poisoning him for years in order to split his fortune (they previously did this to the secretary's rich husband). Unfortunately for the secretary, the wife actually ended up falling in love with him. The secretary still killed him, though, and both get off scot-free. The wife doesn't seem too broken up about his death, however.
- Well, he's not a hitman, but in NCIS, Tony starts dating Jeanne because he's on a mission tracking down her criminal father. This gets rather complicated when he falls in love with her for real when she still doesn't know who he really is.
- On Teen Wolf, hot twins Aiden and Ethan are sent by Deucalion to seduce Lydia and Danny, because one of them will supposedly be very important to Scott. Ethan quickly falls in love with Danny, much to his brother's annoyance. However, Aiden subsequently proves to care for Lydia as well, leading to both twins doing a Heel–Face Turn.
- In both the mini-series and movie versions of State of Play, Sonia Baker is sent in by the company Stephen Collins is investigating to be his personal assistant - thanks to politicians working with that company - and report back on him. She falls in love with Collins - even getting pregnant by him - and tells the company she wants out. Tragically, Collins finds out who she really was, and the Psycho for Hire working for him has her killed.
- Medici: This happens to Maddalena, sent to seduce and spy on Cosimo de Medici during his exile in Venice.
- Though she fell in love with him before he became the mark, the lover of The Last Revolver's Nemesis Sudou is quite important to her, though this doesn't stop her from killing him when she's ordered to. She turns the gun on herself afterwards and survives. After this, she decides to "confront" her boss.
- In Dragon Age: Origins, Zevran is a potential romance option if you spare him after his failed assassination attempt. Justified because it's just business to him and his employers will kill him for failing his mission no matter what he does, so he has no ill will against you. It also helps that he didn't like the assassins guild he worked for and took the mission against you because he thought you'd kill him and, after you spare him, he realizes that you just might be powerful enough to take on the hit squad that will be sent after him for his failure.
- In one of his first missions for the Crows, Zevran ended up sleeping with the Mark. While he didn't fall in love her she had convinced him to talk to his employers about her. Instead she tripped and fell on her head, killing her instantly. Zevran was applauded for making it look like an accident. He wasn't too cut-up about it, as he discovered afterwards she had planned on double-crossing him.
- Also present with the male Warden's romance with Morrigan. She wasn't hired to kill you, but she did intend to be impregnated by you so she could give birth to an Old God. When you find this out and ask Was It All a Lie?, she admits that "loving you...was not part of the plan."
- In Fire Emblem: The Sacred Stones, Joshua meets Natasha and attempts to flirt with her; she runs off, keenly aware of the bounty on her head as a Defector from Decadence. When they meet up later, he flips a coin and tells her to call it in order to determine whether he kills her or not. Note that she is a cleric who is bound by oath not to indulge in vices such as gambling (though this is an understandable excuse). They get married if they achieve an A support.
- And from Blazing Sword (7), we've got Jaffar and Nino. A catch here is that they're both assassins in the organization now run by the Big Bad— and are sent to assassinate the Prince of Bern, Zephiel (a hit put out by the Prince's Fox-kicking Bastard of a Father). However, the organization can't exactly get away with killing someone that important... so Sonia orders the up-to-that-point completely heartless Jaffar to kill her own daughter Nino as a scapegoat for the murder, apparently unaware that Nino had actually saved Jaffar's life in the recent past. Needless to say, that didn't go over well in more ways than 1. Ultimately, this leads to a double Heel–Face Turn and if they get an A-Support, they'll end up married (Although, neither lives much longer after the game, sadly.)
- A weird variation can happen in Awakening. Lucina went back in time to save her father, who was murdered by his closest friend. However, she doesn't realize at first that the Avatar is the killer, and can fall in love with him before either one knows that he's the mark. Which leads to a heartbreaking scene for the two later when Lucina tries (and fails) to kill him.
- Bastila in Knights of the Old Republic. Her real purpose was to watch over the amnesiac Revan to make sure he didn't start to recall any of their former life as Dark Lord of the Sith. Falling in love with him however, wasn't part of the plan.
- Visas Marr in Knights of the Old Republic II joins your party after failing to assassinate you. She is a possible love interest for a male character (though the Handmaiden becomes inordinately jealous).
- Played with in Mass Effect 2: Thane fell in love with the woman that blocked his shot on the Mark. According to Thane she didn't even know his target, and this had a profound affect on him (he still took the shot, just not that day). He tracked her down, begged her forgiveness, and they eventually married.
- A rather twisted version of this trope appears in Metal Gear Solid, in which Sniper Wolf is known for becoming so obsessed with her targets that she falls in love with them... right before she kills them anyway.
- In Sacred, two of the PCs, the Dark Elf assassin and Wood Elf ranger, are lovers. The Dark Elf was supposed to murder the Wood Elf as a rite of passage, but his love for her turns him into a Defector from Decadence.
- The backstory of Kasuga from Sengoku Basara reveals that she fell in Love at First Sight with Uesugi Kenshin, the man she was supposed to assassinate and promptly underwent a Heel–Face Turn for, and has been serving as his bodyguard ever since.
- XIII has one (female) assassin tell XIII that the #1 rule for assassins is not to fraternize with the target, so as not to hesitate at the time of killing. Which of course doesn't stop her from sleeping with him.
- Metal Gear Solid 3: Snake Eater: This one's tricky. Eva is actually a double agent for China. She becomes grossly entangled with Snake, even though she has to kill him at the end of the game to silence his report on the $100-billion legacy. The thing is, she doesn't spare him because she loves him - her spy school trained students for that A LOT. She spares him because HIS mark, who he killed, was an espionage teacher to both of them - and basically, she loves The Boss even more as a stepmother.
- In The Order of the Stick, the half-orc ninja Therkla is ordered by Lord Kubota to kill Elan (in order to get at Hinjo, for whom Elan is currently working as a bodyguard). Therkla instead develops a crush on Elan, defects (to Neutral between their LE and CG at least), and is ultimately killed by Lord Kubota. Elan is unable to prevent this, and takes it kind of hard.
- Something like this is used in The Zeta Project, but it's not romantic love. Zeta is a literal emotionless robot who is designed to infiltrate and eliminate targets without their being aware of the deception. However, after impersonating a man for months, Zeta bonds with the family and develops a heart. Deciding he doesn't want to deny the man a chance to see his daughter grow up (or indeed hurt any living thing again), he abandons the mission and goes on the run. This kicks off the main plot.