%%
%%
%%
%% This list of examples has been alphabetized. Please add your example in the proper place. Thanks!
%%
%%
%%
%% Image selected per Image Pickin' thread: https://tvtropes.org/pmwiki/posts.php?discussion=1560517217070992500
%% Please do not replace or remove without starting a new thread.
%%
[[quoteright:350:[[WesternAnimation/{{Futurama}} https://static.tvtropes.org/pmwiki/pub/images/bender_fanny_donbot.png]]]]
[[caption-width-right:350:[[CharacterCatchphrase "Well, I'm boned."]]]]
%%
%% Caption selected per above IP thread. Please do not replace or remove without discussion in the Caption Repair thread:
%% https://tvtropes.org/pmwiki/posts.php?discussion=1404492079030138900
%%

->'''Ada:''' I'm with you 'cause you're the only man 'round here ''not'' scared of them.\\
'''Freddie:''' Oh, I'm scared of them, all right.\\
'''Ada:''' But you love ''me'' more than you fear ''them'', right?
-->-- ''Series/PeakyBlinders''

Who is that? She's perfect. She's a vision. She's like no one you've ever seen. You've got to get to know her, to learn everything about her.

Wait. She's got a boyfriend? OhCrap. And her boyfriend is ''that guy''? [[FromBadToWorse It just got worse.]]

Many a tale has been told about a poor schmuck who fell in love with a beautiful woman, only to find out she [[AllGirlsWantBadBoys likes someone very dangerous]]. Usually, the [[TooDumbToLive dumb cluck]] will [[DoggedNiceGuy persist in trying to win her heart]] and "take her away from all this". Depending on where the story lies on the SlidingScaleOfIdealismVersusCynicism, our hero may get the girl in the end and get away clean, or one or both of them may end up [[MurderTheHypotenuse very, very dead]]. Or he may [[TakeAThirdOption do the sensible thing]] and [[ScrewThisImOuttaHere get out while the getting's good]]. But then [[AnthropicPrinciple there wouldn't be much of a story]], would there?

Sometimes both of the guys in this rather deadly LoveTriangle are crooks, but the one with the relationship is someone higher up on the food chain, whether by being higher up in the criminal hierarchy (such as TheDon in a mafia story) or by being vastly more dangerous than the other.

Compare MafiaPrincess.

----
!!Examples
[[foldercontrol]]

[[folder:Anime & Manga]]
* A one-shot character in the ''Manga/BlackJack'' manga does this by accident; he's fallen in love with Pinoko's voice, and a coincidence makes him think the gangster's girlfriend is the one with angelic vocal cords. She isn't, and the would-be suitor makes a quick getaway.
* This is what set up the tragic LoveTriangle between Spike, Vicious and Julia in ''Anime/CowboyBebop''. Especially tragic because Spike (who was a [[TheSyndicate Red Dragon]] member himself) and Vicious used to be the best of friends before this.
* Ian from ''Manga/ACruelGodReigns'' has a fling with a gangster's wife, although it turns out that he is possibly only a soldier.
* A story in ''Manga/PetShopOfHorrors: Tokyo'' has a small-time {{yakuza}} member fall in love with his boss's girlfriend, who he knew in high school. [[spoiler:When the boss tries to frame the member for a crime, the girlfriend agrees to run away with the guy. It ends [[BittersweetEnding not so great]]. The guy falls into the ocean and seemingly drowns so that the girl can escape. The girl is later seen telling a police officer the story, implying that she made it. It later turns out that the yakuza member was turned into a dog and taken in by one of D's purebreds.]]
[[/folder]]

[[folder:Comic Books]]
* ''ComicBook/JewGangster'': Molly, the wife of the local mob leader Monk Shapiro, throws herself at up-and-coming gangster Reuben Kaplan. He soon reciprocates in kind, despite the risks.
[[/folder]]

[[folder:Film -- Live Action]]
* Bertram Potts for Sugarpuss in ''Film/BallOfFire''.
%%* ''Film/BlueVelvet''
* Emma, Harry and Paul in ''Theatre/BornYesterday''.
* ''Film/{{Bound 1996}}'' is a GenderFlip version, or half of one. A lesbian ex-con falls in love with a mafioso's girl, and the girl reciprocates. Then they hatch a scheme to get rid of him, which ends up backfiring on them when he proves to be far more resourceful than either of them anticipated.
* ''Film/TheCookTheThiefHisWifeAndHerLover'' is a good example of the "doesn't turn out well for the guy" version.
* In ''Film/TheCottonClub'' Dixie Dwyer is a singer who is in love with Vera Ciciero- who happens to be Dutch Scultz's girlfriend. Dutch is not pleased.
* In ''Film/DickTracy'', 88 Keys feels this way about Breathless Mahoney, whom Big Boy Caprice appropriated from one of his rivals after sending said rival to his death.
* In ''Film/TheFastAndTheFuriousTokyoDrift'', Sean manages this ''twice'' - first in the prologue with the school bully's girl. It doesn't end well, and he ends up on the next plane to Tokyo. There, he falls for Neela - her boyfriend, DK, is a Yakuza associate on top of his standing in the drifting community.
* ''Film/TheGirlCantHelpIt'' ends up being this. [[spoiler:Fortunately, the gangster realizes he was just pushing his girl to help him get back his GloryDays. Once he finds his own way, he lets her go.]]
* ''Film/TheHitman'': Garret, an undercover cop working as a hitman for the mafia, has a fling with a mob accountant who also happens to be the mistress of the boss he's working for. He finds out. She eventually ends up with a bullet to the back of her head, Garret ends up getting sold out to the competition.
* ''Film/JamesBond'':
** Expectedly, there have been quite a few [[GirlOfTheWeek Bond Girls]] who were the girlfriend/mistress/wife of the BigBad: Domino Derval from ''Film/{{Thunderball}}'', Solitaire from ''Film/LiveAndLetDie'' (though she had a platonic relationship with the BigBad, to preserve her [[VirginPower psychic abilities]]), Andrea Anders from ''Film/TheManWithTheGoldenGun'', Kara Milovy from ''Film/TheLivingDaylights'', Lupe Lamora from ''Film/LicenceToKill'', Paris Carver from ''Film/TomorrowNeverDies'' (who also happened to be one of Bond's former lovers), and Severine from ''Film/{{Skyfall}}''. Additionally, in ''Film/CasinoRoyale2006'', Bond beds Solange Dimitrios, wife of TheDragon Alex Dimitrios. As befitting the darker aspects of this trope, [[MurderTheHypotenuse fully half of these women do not survive their respective films.]]
** ''Film/OnHerMajestysSecretService'' provides a subversion - the Bond Girl is the daughter of a gangster, but the gangster in question is Bond's ally. [[spoiler: Unfortunately, she fares no better than the unlucky Bond Girls above.]]
** Averted in ''Film/{{Spectre}}'', where Lucia Sciarra is the ''widow'' of this type of man, thanks to Bond killing her husband, but in no less danger from his vengeful associates. She manages to be one of those who survive. There's also a variant in the movie with Madeleine Swann, Mr. White's daughter, who becomes Bond's ally and love interest as he goes after SPECTRE.
* ''Film/KingCreole'': Troubled high school dropout Danny falls in love with Ronnie, the moll of nightclub owner and gangster Maxie Fields. It ends badly, with Ronnie shot dead by Maxie.
* ''Film/LittleShopOfHorrors'': Seymour is in love with Audrey, who is the abused girlfriend of a sadistic dentist.
* In ''Film/LostHighway'', Pete gets in deep with Alice, the gangster boss' girl.
* ''Film/MadDogAndGlory'' has a crime scene photographer and the bartender at the bar of a mob guy whose life he saved. Mad Dog learns that Glory is trying to pay off a personal debt to Milo, the aforementioned mob dude, and after coming up short of the money needed, he has to fight Milo, after which they make peace and Milo lets Glory go.
* This sets up the final tragedy of ''Film/ElMariachi''. Here, the title character falls in love with Domino, the girlfriend of druglord Moco. The Mariachi survives, but Domino isn't so lucky.
* The movie ''Film/TheMarryingMan'' starts with the protagonist sleeping with a woman who turns out to be the girlfriend of the notorious gangster "Bugsy" Siegel. Uncharacteristically the gangster is a good sport about this and rather than having the couple killed, he [[ShotgunWedding has them marry each other]].
* ''Film/TheMask'': Stanley Ipkiss falls in love with Tina, the girlfriend of Dorian the gangster. It results in a big showdown between the two of them, once Ipkiss gets the mask back. And it's Tina who decides she likes Stanley enough to leave Dorian, rather than Stanley trying to take Tina away.
* Played with in ''Film/PulpFiction''; Vincent senses the rising tension between him and Mia and explicitly warns himself to avoid this trope. Not in the least because there's a rumor circulating that his boss Wallace crippled one of his other employees for screwing around with his wife, although Mia herself denies this was the reason and thinks that incident was strictly business-related.
* Elvira, drug lord Frank Lopez's girlfriend in ''Film/{{Scarface 1983}}''. She eventually marries Tony, but the lifestyle of a druglord isn't very conducive to a happy relationship, especially since Tony disregarded her advice about [[GettingHighOnTheirOwnSupply not getting high on his own supply]], leading to Tony becoming [[SanitySlippage increasingly unstable]] and costing him his relationship with her.
* An in-universe one in ''Film/SinginInTheRain''; in the FilmWithinAFilm ''The Dancing Cavaliers'', Gene Kelly's character has a DreamSequence where he imagines himself falling for Creator/CydCharisse, but ultimately losing her to her mobster boyfriend.
* Played with in ''Film/{{Solo}}''. Han Solo discovers his old girlfriend Qi'ra, whom he still loves, is now the right-hand woman of powerful gangster Dryden Vos, with both of them making it pretty clear Vos [[ResignationsNotAccepted won't let her go without a fight.]] It's not made explicit that there's a romantic/sexual relationship between them, though some of Vos' behavior towards Qi'ra indicates he [[ShipTease doesn't just think of her as his employee]]. Han being Han, he ignores everyone's warnings to pursue Qi'ra anyway, offering to take her away from Crimson Dawn to begin a new life. [[ForegoneConclusion It doesn't end well.]]
* In ''Film/TheWholeNineYards'', Nicolas "Oz" Oseransky falls for Cynthia Tudeski the estranged wife of Jimmy "The Tulip" Tudeski. Fortunately for Oz, Jimmy falls for fellow assassin Jill and moves on with his life.
* In the movie ''Film/WildSide'' Alex falls for Virginia who is involved with international smuggler Bruno. A LesYay version of the trope (Alex is a girl).
[[/folder]]

[[folder:Literature ]]
* Leads to the final fate of [[spoiler: the main character]] in ''Literature/TheBriefWondrousLifeOfOscarWao''.
* A key element in the Creator/IainBanks story "Dead Air". The relationship and the potential consequences of ''that guy'' finding out drive much of the plot.
* The Creator/StephenKing story "The Ledge" from ''Literature/NightShift'' deals with a man who falls in love with a gangster's wife and is forced to walk a ledge all the way around an apartment building. It's very high up and the ledge is six inches wide. If he wins, he gets the girl, n.q.a. If he loses, he falls to his death. This guy being a criminal, of course, there's a rather nasty loophole in the deal.
* Through sheer coincidence, Teddy Telemachus from ''Literature/{{Spoonbenders}}'' winds up in a relationship with Graciella, daughter-in-law to TheDon Nick Senior, who had just separated herself from her husband after he's arrested on murder charges. Of his own volition, he enlists Irene's help so that she can become finally stable enough to leave for good and is forced to pay off Frankie's MobDebt for him in the hopes that his family won't be further involved.
* The Creator/SidneySheldon novel ''A Stranger In The Mirror'' twists this around. The protagonist, a famous comedian, beds a gangster's mistress, but he has no interest in her beyond a one-night stand. Regardless, he's still terrified when the gangster and his cronies show up on his doorstep, only to have the gangster pull an IWantMyBelovedToBeHappy and demand that he marry the girl, as she's head over heels in love with him. Given the kind of man he is, he threatens him anyway, pairing this with an IfYouEverDoAnythingToHurtHer.
* The deuteragonist of ''Literature/TheValleyOfFear'' deals with this by gaining the favor of the gang himself. It does get his rival to back off, but needless to say, the love interest is not thrilled.
[[/folder]]

[[folder:Live-Action TV]]
* In the second season of ''Series/BoardwalkEmpire'', Owen, an IRA enforcer who works for Nucky, starts pursuing and eventually sleeps with Nucky's mistress Margaret. Since the show has some of the same creators as ''Series/TheSopranos'', comparisons between Owen and Furio happened almost immediately.
* A modern retelling of ''Literature/TheCanterburyTales'' on the BBC featured this trope in an adaptation of "The Sea Captain's Tale". In the original, the cuckolded husband is a ruthless banker/usurer with a manipulative, extravagant wife. In the adaptation, the usurer is TheDon of a South-Asian community and is a money lender and "importer/exporter". In both versions, the seducer borrows money from the husband on her behalf. In the modern version, the guy is more innocent, and the husband is a CrazyJealousGuy, so things don't go well.
* ''Series/{{Castle|2009}}'' had an episode "The Blue Butterfly" involving the 50-year-old diary of a gritty private eye, a scuzzy crime boss, a gorgeous gun moll, and a diamond-encrusted butterfly. That one actually turned out very nicely.
* In ''Series/{{Flashpoint}}'', an undercover agent becomes involved with the drug leader's girlfriend and his actions to protect her while bringing down the drug gang only led to trouble for him, her and Team One.
* ''Series/NipTuck'': Subverted in the pilot episode. Sean and Christian treat a Colombian client, Silvio Perez, that Christian quickly figures out is a drug trafficker. Perez admits he's on the run for "sleeping with the boss's girl". Christian, a shameless Casanova, accepts this reason. It later turns out that Perez is a pedophile who raped the boss's ''daughter''. The boss, Escobar Gallardo, murders Perez on the operating table.
* In the third episode of ''Series/QuantumLeap2022'', Ben discovers that his leapee, a boxer named Danny, is in a secret relationship with the girlfriend of his boxing opponent.
* In the ''Series/{{Seinfeld}}'' episode "The Friar's Club," Kramer dates a girl who refuses to be seen with him in public. It turns out to be for this reason. The real danger is (unintentionally) from her, however; when Kramer falls heavily asleep at her apartment (having been recently attempting polyphasic sleep, which left him seriously sleep-deprived) and she thinks he's dead, she calls some friends to dump the "body" into the Hudson River rather than have her boyfriend find out that she was cheating. Kramer escapes but never finds out what was really going on, assuming she tried to have him killed [[IfICantHaveYou to keep anyone else from having him]].
* In ''Series/TheSopranos'', Furio gradually falls in love with Carmela Soprano after seeing her day after day while coming by to pick up Tony Soprano every morning. Furio himself is a dangerous Made Man in the Mafia, but Tony is ''the Boss''. Furio's uncle eventually tells him that he can either abandon his love for Carmela, or [[MurderTheHypotenuse kill Tony]]. Furio does almost go ahead with killing Tony, but backs out and flees the area instead.
* In the ''Series/StarTrekTheNextGeneration'' episode "The Royale", Riker, Data and Worf are stuck in a virtual reality simulation of a poorly written book where the bellhop at the eponymous hotel/casino is in love with a gangster's moll. The bellhop has a gun with which to "deal" with the gangster, but the gangster kills him instead.
-->[[BondOneLiner You should have listened to me, kid.]] No woman's worth dying for. ''Killing'' for, not dying for.
* In ''Series/TwinPeaks'' Juvenile delinquent Bobby Briggs is having an affair with Shelly Johnson, the wife of the more seasoned criminal Leo Johnson
** Also [[spoiler:Sheriff Truman and Josie Packard.]]
[[/folder]]

[[folder:Manhwa]]
* ''Manhwa/TheTarotCafe'' has a Theatre/RomeoAndJuliet love story between the daughter of a mob boss and the son of a rival boss. Both know full well what will happen, but choose to elope. The daughter's magic pet cat is also in love with her, but no one actually knows about it. [[spoiler:The cat later dies so the daughter and her boyfriend can escape.]]
[[/folder]]

[[folder:Music]]
* The song "[[http://youtu.be/p7Mi2-_4bTA Solomon Jones]]" by Aceyalone & Music/RJD2 ends in a shootout between "Big Bad Solomon Jones" and a mysterious man who had wandered into his bar, all over "the lady known as Simone".
-->''Then all of a sudden the music changed, and everyone just held their pulse\\
But it felt like your life had been robbed from you, and everything that you held close\\
That someone had stolen the woman you loved, and that her love was a devil's lie\\
That your heart was gone, and the best thing that you could do was crawl away and die\\
It's the painful cry of a man's despair, deep down in his bones\\
"I guess misery enjoys company", said big bad Solomon Jones''
* {{Inverted}} with Jim Croce's "Bad, Bad Leroy Brown." Leroy is used to having what he wants, sexual conquests included. He makes the mistake of trying to bed "the wife of a jealous man" and ends up having his ass kicked in full view of the neighborhood.
* {{Downplayed|Trope}} and PlayedForLaughs in Jay and the Americans "Come a Little Bit Closer." The narrator is in a bar and the girlfriend of "Bad Man Jose" flirts with him. Attracted, he has a dance and kisses her...but then Jose shows up and he jumps out the window to avoid Jose's wrath. The girlfriend, without skipping a beat, goes and uses the same come-on lines on Jose she was using on him.
* {{Inverted|Trope}} with "Copacabana" by Music/BarryManilow. A gangster sexually harasses the showgirl the bartender's committed to. It gets the bartender killed, and the showgirl ends up as a broken alcoholic.
* In "[[https://www.youtube.com/watch?v=1o1oizc4_3I El Paso]]" by Marty Robbins, both the male love interests end up dead.
-->''One night a wild young cowboy came in\\
Wild as the West Texas wind\\
Dashing and daring, a drink he was sharing\\
With wicked Felina, the girl that I loved''
* Music/BonnieTyler: The theme of the song "Hide Your Heart", which was in part written by Music/{{KISS}} member Paul Stanley, but the band did not do a version until after Tyler. It tells the story of Johnny, a boy who was in love with a girl called Rosa who was the girlfriend of a gang leader named Tito. Even after Rosa told Johnny that they couldn't be together, Tito caught wind of the situation and sought to kill Johnny. Unfortunately for Rosa, Tito succeeds.
* Music/CharmingDisaster's "Showgirl" is about a New York nightclub performer who catches the eye of a police officer who's investigating the Mob... which happens to be run by her ''actual'' boyfriend. After the cop gets her mobster boyfriend sent to prison, the showgirl takes up with him, but it's unclear if she has any actual affection for either of the men or if she's just being pragmatic. One of the song's writers, Jeff Morris, has stated the song is inspired by his great-aunt, who ''actually did'' date both a mobster and a cop simultaneously in the UsefulNotes/TheRoaring20s.
[[/folder]]

[[folder:Newspaper Comics]]
* ''ComicStrip/{{Luann}}'': Luann's brother Brad fell in love with his next-door neighbor Toni Daytona. Unfortunately, she turned out to have an emotionally abusive and dishonest boyfriend named Dirk, who was extremely muscular and could have broken Brad in half without trying.
[[/folder]]

[[folder:Theatre]]
* This was the plot of the 1921 musical ''Theatre/GoodMorningDearie'', where it led to the first act ending with a fight scene.
[[/folder]]

[[folder:Video Games]]
* In ''VideoGame/FalloutNewVegas'', Bruce Isaac is a former lounge singer from New Reno who's in hiding after stealing money from a mob boss as well as the fact that he, in his own words, "might have... sort of... plowed his daughter. A little".
* In ''VideoGame/GrandTheftAutoIII'', player character Claude gets in serious trouble when TrophyWife Maria tells her husband/Claude's boss Salvatore Leone that they've been having an affair, forcing Claude to abscond to a different part of the city.
[[/folder]]

[[folder:Western Animation]]
* The Donbot's wife on ''WesternAnimation/{{Futurama}}'''s episode "[[Recap/FuturamaM4IntoTheWildGreenYonder Into the Wild Green Yonder]]" cheats on him with Bender. They're... less than subtle about their relationship.
* Henchmen 21 has a crush on Dr. Mrs. The Monarch on ''WesternAnimation/TheVentureBrothers''. She's fairly dangerous herself, but her husband (guess who) is fairly cavalier about killing his henchmen if they so much as take him by surprise. [[spoiler:He eventually quits his job when he's no longer able to handle working with her and the other mounting psychological issues the job's causing him.]]
[[/folder]]
----