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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.
Love has a way of sniping even the coldest heart, and against all sanity and better judgement the [[Hitman
At first he'll make increasingly implausible excuses to his superiors at the [[Murder, Inc.|assassin's guild]] to [[Even Evil Has Loved Ones|justify not killing]] his [[Love Interest]], even [[I Was Just Passing Through|protecting her from rival hitmen]] until ultimately they decide he's gone rogue and put a [[Contract
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
{{examples}}▼
▲{{examples}}
== Anime and Manga ==
* Rethink your definition of "love", and you have Seishirou Sakurazuka from ''[[
* ''[[
* Rolo in ''[[
* Ironically played with in ''[[
* In ''[[
* One episode of ''[[Noir (
* ''[[El Cazador
▲* Rethink your definition of "love", and you have Seishirou Sakurazuka from ''[[Tokyo Babylon (Manga)|Tokyo Babylon]]'' and ''[[X 1999 (Manga)|X 1999]]''.
* 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.
▲* ''[[Crying Freeman (Manga)|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 (Anime)|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 (Anime)|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 ''[[Risky Safety (Anime)|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. [[Star-Crossed Lovers|Much to their respective armies' dismay.]]
▲* 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.
▲== Fan Fiction ==
* The somewhat, um, '[[Memetic Mutation|infamous]]' ''[[Warhammer 40000 (Tabletop Game)|Warhammer 40000]]: [[Dawn of War]]'' fanfiction "Love Can Bloom".▼
▲* 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.
* ''[[Undercover Brother]]''. After falling in love with the title character, {{spoiler|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 [[Lampshade Hanging|lampshaded]] in a conversation between Jill and fellow hit-man Jimmy "The Tulip" Tudesky:
{{quote|
'''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.
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* ''Prizzi's Honor.''
* Wild Target, he is initially unable due to chance to kill her, 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 (
* 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 ''[[
▲== Live Action TV ==
▲* Cole (Belthazar) from ''[[Charmed (TV)|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
** 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 [[Becoming the Mask|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.)
* {{spoiler|River Song}} from [[Steven Moffat]]'s run of ''[[
* On ''[[
* On ''[[Leverage]]'', during "The Lonely Heats Job" a con artist falls in love with her rich husband and ends up disapearing 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 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 ==
* ''[[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.
* In ''[[
** 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.
* Visas Marr in ''[[Knights of the Old Republic (
* Played with in ''[[
* 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 ''[[
* A rather twisted version of this trope appears in ''[[
* 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 ''[[
== Western Animation ==
* Something like this is used in ''[[
{{reflist}}
[[Category:Romance Arc]]
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