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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}}
== 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
== Fan Fiction ==
* The somewhat, um, '[[Memetic Mutation|infamous]]' ''[[
== 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.
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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.
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== Live Action TV ==
* Cole (Belthazar) from ''[[
* 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.
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== 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 ''[[
** 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 [[Kick the Dog|Fox-kicking]] Bastard of a Father). However, the organization can't exactly get away with killing someone that important... so [[Evil Matriarch|So]][[Complete Monster|nia]] order [[Defrosting Ice Queen|the up-to-that-point completely heartless]] [[Tyke Bomb|Jaffar]] to kill ''her own daughter'' [[Token Mini-Moe|Nino]] as a second target, apparently unaware that [[Florence Nightingale Effect|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, [[Doomed
* 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 ''[[The Order of the Stick
== Western Animation ==
* Something like this is used in ''[[
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