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{{trope}}
{{quote|''"Do what? Do I ice her? Do I marry her? Which one of these?"''
|'''''Prizzi's Honor'''''}}
The [[Career 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.
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The former target cum [[Love Interest]] will of course be ''really'' freaked out [[Third-Act Misunderstanding|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. It seems 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 [[What Measure Is a Mook?|former colleagues]] and innocents. Now that he's essentially done a [[Gender Flip
{{examples}}
== Anime and Manga ==
* Rethink your definition of "love", and you have Seishirou Sakurazuka from ''[[Tokyo Babylon]]'' and ''[[X (manga)|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 [[Becoming the Mask|posing as his younger brother to monitor him]] and saves his ass ({{spoiler|[[Heroic Sacrifice|which kills him]]}}).
* Ironically played with in ''[[Rurouni Kenshin]]''. [[Career Killer|Assassin]] Kenshin and Tomoe fall in love with each other. However, {{spoiler|the mark is Kenshin, not Tomoe, who is a spy for Kenshin's [[Genre Savvy]] enemies, who intended to invoke this trope on purpose in order to use her as a hostage and lure Kenshin into a trap.}}
* In ''[[
* One episode of ''[[Noir (anime)|Noir]]'' has Kirika befriending a target. {{spoiler|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.
== Comic Books ==
* Probably the case with Yith, a [[Snake People|snake-woman]] [[Professional Killer|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. The story ends there, with Yith leaving without any further explanation.
== Fan
* The somewhat, um,
== Film ==
* Played with in [[Grosse Pointe Blank]]. The hitman is actually in love with {{spoiler|his mark's daughter.}}
* ''[[
* ''[[Mr. and Mrs. Smith]]'' inverts this. The two characters fall in love and get married, neither knowing the other is a secret agent, and then later, they're instructed by their respective organizations to kill each other.
* The movie ''Portrait of a Hitman''. I don't know about 'falling in love with' but he can't pull the trigger on her.
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* Subverted in ''[[Red Eye (film)|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.
== Literature ==
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* ''[[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.
▲== Live Action TV ==
* 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.
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* 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 secreatary still killed him, though, and both get off scot-free. The wife doesn't seem too broken up about his death, however.
== Video Games ==
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* Visas Marr in ''[[Knights of the Old Republic (video game)|Knights of the Old Republic]] 2'' 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, eventually tracking her down and marrying her.
* In ''[[Fire Emblem:
** 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]]
* 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.
* 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]].
== Web Comics ==
* In ''[[The
== Western Animation ==
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{{reflist}}
[[Category:Romance Arc]]
[[Category:Redemption Tropes]]
[[Category:{{PAGENAME}}]]
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