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2* In ''[[http://www.fimfiction.net/story/93809/a-pleasant-surprise A Pleasant Surprise]]'', this trope is zig-zagged. It's an inferred reason that he has little experience with girls. An aversion of this trope is why he and his love interest get together.
3* In the Manga/OnePiece fanfic ''Fanfic/AbyssCronicaCaptive'' [[https://www.deviantart.com/abysscronica/gallery/64643468/captive-eustass-kid-x-reader Captive]] the main female character Birdie ends up falling in love with Captain Eustass Kidd of all people.
4* Gender-Inverted in the ''Franchise/MarvelCinematicUniverse'' fanfic ''[[https://archiveofourown.org/works/31456490 The Artist's Garden at Madripoor]]'', where Steve goes to [[Series/TheFalconAndTheWinterSoldier Madripoor]] in order to acquire the last component for the [[Film/AvengersEndgame Quantum Tunnel]] and discovers that [[TheQueenpin Sharon is the Power Broker]], the city's JudgeJuryAndExecutioner. While he's shocked and saddened by [[FallenHero her fall from grace]] and [[ItsAllMyFault blaming himself for it due to basically just leaving her behind]] [[DeconstructionFic after she threw away her career in the CIA to steal back his shield in]] ''Film/CaptainAmericaCivilWar'', he does find himself attracted to the new edge she displays.
5* ''Fanfic/TheBoltChronicles'':
6** In "The Cameo", Tracey is sexually attracted to the caddish Blaze even though she doesn’t much like him personally, a fact she acknowledges openly. Also, Penny has a tryst with teen heartthrob Lance – someone even Bolt can see is a self-absorbed dolt.
7** In "The Survivor", Emily marries gang member Jack, staying with him despite his [[DomesticAbuse physical abuse]], horrific temper, [[DrugsAreBad drug and alcohol addiction]], and [[BadPeopleAbuseAnimals mistreatment of animals]].
8** All of Penny's classmates find Dr. Vanderbilt, the new HotTeacher at school, [[PrecociousCrush to be extremely attractive]]. He wears a leather jacket and sunglasses, and Penny's chemistry lab partner friend describes him as "the perfect combo of genius smarty and biker hottie."
9* In ''Fanfic/CalamityJaneMeetsDoctorIsles'', this trope is the reason Jane finds it easy to create a reputation that her male disguise, Jake Wyatt, is a ladies' man when she's never actually ''done'' anything, although this is also the reason that Charles Hoyt won over at least one of his apprentices.
10* ''Fanfic/CaptiveAbyssCronica'': Kid is certainly the baddest Supernova. It does not take Birdie long to become physically attracted to him and even fall in love. Also Ross, a very popular prostitute in John's Dockyard is madly in love with Kid.
11* In ''Fanfic/DekuInClass1B'', the religious and NiceGirl Ibara has feelings for the foul-mouthed Awase.
12* ''Fanfic/DemonOfJustice'' Zigzags and plays with this trope. Rami pines after the scary handsome demon and gets dressed up to say goodbye to him...because it's just like what's in the stories. She doesn't mind that he's going, though, because she can't picture him settling down and having kids with her. Wufei is just thankful to get away from her, and is, in fact, prone to hiding in Nantaku until he left the village.
13* ''FanFic/EdenObsessmuch'' deconstructs this. Hermione's growing interest in Lucius is treated as damaging and shows why any interest in someone as abusive and violent as him is a bad idea.
14* ''Fanfic/ForGood'', a ''WesternAnimation/BuzzLightyearOfStarCommand'' series, is perhaps best known for the romance between Erin, the protagonist, and Warp Darkmatter, the Evil Emperor's right-hand man. In the introductory fic, ''Breakaway'', their relationship actually begins innocently enough, at least on Erin's part. Warp comes off as less of a villain and more as a JerkWithAHeartOfGold.
15* The ''VideoGame/TheElderScrollsVSkyrim'' mod, [[https://skyrimromance.com/skyrim-romance-3-0-released/ Skyrim Romance]] by Maralightfeather, heavily features a bad boy romance option in the follower, Bishop. Heavily based on, to the point where some say it's straight up copied from the same character from ''VideoGame/NeverwinterNights2'', if Bishop is interacted with, he'll come across as incredibly condescending, misogynistic, possessive, and borderline abusive towards the female Dragonborn, but despite being incredibly aggressive towards mostly everyone else, treats the Dragonborn somewhat differently as time progresses. The mod has received its fair share of criticism for the copied source material, and abusive portrayal of Bishop.
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17* In ''Fanfic/ForumOfThrones'', this is Rosalie's motivation for her feelings for Philip, despite the fact that he is older than her and clearly not interested. [[spoiler: She eventually gets in contact with a truly bad boy when she meets [[SerialKiller Wolfius]], though that is decidedly not the kind of attention she wanted.]]
18* ''Fanfic/GuysBeingDudes'': Gender-Inverted with Spark. He describes both of his love interests as having "dark and edgy vibes". Arlo specifically works for a criminal organization and Candela mentions Spark's ex as having possibly been a supervillain.
19* In the first part of ''Fanfic/TheHeartTrilogy'', [[{{Seers}} Kathryn]] is taken prisoner by [[VillainProtagonist Smaug]], "the Chiefest and Greatest of Calamities" who wants to keep her beautiful singing voice all to himself. However, [[AMatchMadeInStockholm she gradually falls in love with the homicidal dragon]], realizing her feelings for him when [[LimaSyndrome he lets her go and enjoy her freedom]]. However, it should be noted that Kathryn's attraction doesn't stem from Smaug's evilness but from the fact that he's the first person in her life who didn't [[AllTheOtherReindeer fear or despise her because of her clairvoyant abilities]], [[BecauseYouWereNiceToMe helped her, supported her, and fully accepted her]]. Plus, he's so dangerous that few people would dare try to hurt her as long as she remains with him, which is appealing since [[DarkAndTroubledPast she has spent most of her life being hurt and victimized one way or another]]. This becomes a bit deconstructed later in the trilogy, for Smaug's stubborn refusal to tone down his violent and greedy tendencies brings sorrow to Kathryn to the point that she runs away from him in the trilogy's second part and agrees to give her heart to him only when he finally agrees to give up his murderous ideas to conquer Erebor back.
20* In ''ComicBook/{{Supergirl}}'' fanfic ''Fanfic/HellsisterTrilogy'', the Girl of Steel falls for Dev-Em, a reformed bully and former teenage delinquent who is still kind of jerkass.
21* In ''WesternAnimation/{{Ben 10}}'' [[http://www.fanfiction.net/s/4267279/1/Hero-High-Sphinx-Academy Hero High: Sphinx Academy]], Gwen is shown to still be in love with the now revealed BigBad. However this is deconstructed as she is in love with him because despite being the BigBad, he was one of the few people outside of her family to be nice to her, accepting of who she was, and even encourage her.
22* In Chapter 29 of ''Fanfic/IAmNOTGoingThroughPubertyAgain'', [[spoiler:12-year old]] Sasuke muses a WallOfText on how he not only finds this trope ''stupid'' but '''[[DontYouDarePityMe insulting]].'''
23-->Sasuke didn't see himself as a charming person. He had no idea what all those girls saw in him, to be frank. He was bitter, asocial, wrapped in darkness and scarred by grief. The phrase "damaged goods" surely existed solely to describe people like himself.\
24He was not the kind of person that he thought a smart or self-respecting girl should pursue. Couldn't they see how messed up he was? How dangerous a path he would have to walk?\
25It galled Sasuke that so many girls should be so smitten with him. It felt insulting, somehow, like their infatuation devalued the tragedy of his clan's destruction, romanticizing his pain and frustration into an unrecognizable caricature of the person he really was.\
26Their smiling, giggling, blushing, and cooing all angered him. Like they saw it all as one big game, like they didn't take anything seriously. They didn't get it. They refused to understand.
27* In ''Fanfic/KyonBigDamnHero'', several nameless girls and [[OCStandIn Michikyuu Kanae]] react like this when [[spoiler:Kyon is in delinquent mode, breaking up an illegal photography ring with {{Yakuza}} links.]]
28* For ''Fanfic/LePapillonRising'' this is the only explanation for why Marinette decides to crush on Papillon, who happens to also be Adrien, who she's already dating.
29* Inverted in ''Fanfic/LostInCamelot''; despite Bo and Morgana’s canon attraction to dangerous men, they both develop feelings for Merlin due to his genuinely good nature.
30* ''Fanfic/TheManyDatesOfDannyFenton'' (''WesternAnimation/DannyPhantom'' WesternAnimation, [[{{Series}} TV Series]], and ComicBooks.): [[DefiedTrope Defied]]. According to Musa from WesternAnimation/WinxClub, she had a thing for bad boys but is now interested in meeting a NiceGuy that she can get along with.
31* A subverted same-sex example from the ''Anime/KillLaKill'' fanfic, ''Fanfic/NaturalSelection''. Mako is in love with and in a relationship with Ryuko, but she's shown to dislike her negative qualities as much as everyone else does. She's actually attracted to the more gentle, loving Ryuko that lies beneath all the angst, brooding, and blood-lust.
32* In ''Fanfic/TheNightUnfurls'', this trope is the root of [[CelibateHero Kyril's]] UnwantedHarem. For some reason, women having the hots for an aloof, brusque, brooding, [[TheStoic stoic]], mysterious, [[TallDarkAndHandsome somewhat handsome]] AntiHero is beyond his comprehension. Although he is anything but [[JerkAss a complete jerk]], he doesn't think the women deserve to be hooked up with a violent, broken HunterOfMonsters like him. [[spoiler:Him being a [[HumanoidAbomination humanoid great one]] is another factor.]]
33-->''"[[LampshadeHanging Kyril did not understand why that was happening]]. He killed people on a daily basis and already women were trying to line up at his door."''
34* In ''[[https://www.fanfiction.net/s/10256543/1/Nymphadora-s-Beau Nymphadora's Beau]]'' Tonks' mother uses Tonks' tendency toward this trope to encourage her to gravitate toward Harry instead of Remus by making Harry ''seem'' like a "bad boy" and pretending to disapprove of him.
35* Defied in ''Fanfic/TheOneWithTheAngelicFace''; when Angelus's curse also turned him into a female vampire who calls herself Angela, after Toth's wand splits Angela into a human woman and a male vampire, Buffy clearly reflects that she isn't attracted to Angelus even when trying to imagine how she'd feel if it was Angela in the male body.
36* In ''Fanfic/PerfectionIsOverrated'', Makoto Kagami, a shapeshifting [[ParodySue SUE]] in [[Anime/MyHime Mai]]'s image, takes an interest in [[ManipulativeBastard Nagi]], convinced that there's good in him and that [[LoveRedeems her love will change him]], even as he plans on using her to [[spoiler:betray the Usurper, who has possessed his master, the Obsidian Lord]]. Makoto's superficial attraction to Nagi ends up having severe repercussions... [[spoiler:for Nagi, who gets killed when Makoto's Child is destroyed as a result of her own death]].
37* Considered and defied in ''Fanfic/ThePowerOfSeven'' when analysing Demelza Robbin's desire to be sexually dominated; Katie Bell muses that most of the 'alpha guys' at Hogwarts who could dominate Demelza in that way would be selfish in bed and generally just use their confidence to hide their insecurities, while she can see Harry as possessing the right balance of confidence and compassion to pull it off.
38* ''[[https://archiveofourown.org/works/37871560 The Reason Why All for One has 69 Endurance Quirks ]]'': All For One has literally ''hundreds'' of children over the centuries he's been active. The only named characters stated to not be descended from him are Aizawa, Spinner, and Shigaraki. Heck, the week All Might defeated him at Kamino, he'd had a planned date with both Mirko and Ryukyu.
39* Lampshaded in ''Fanfic/ShadowsOverMeridian''. When Quinn expresses disbelief at Rosetta being romantically interested in [[AxCrazy Tyrian]] and another soldier complains that the madman has better luck with women than him, a third soldier guesses that a dangerous man is loved by women.
40* In ''WebVideo/SuperTherapy'', this is Franchise/WonderWoman's main problem -- the therapist describes it as her Kryptonite. This is illustrated by Travis, her complete {{slimeball}} of a boyfriend, who's revealed to have cheated on her thanks to the [[TruthSerums Lasso of Truth]].
41%%* Frequently deconstructed or subverted in "Fanfic/TheLightInTheDark": Deconstructed with Bertha's and Florence's infatuation with Alton Avery. Subverted by Maria Zabini, who is either drowning in denial or genuinely believes that Mulciber is really a good person. Snape seems to believe this, as he thinks that becoming a powerful dark wizard will make Lily attracted to him. Mrs. Jorkins has been going out with Terrance Banks for years, who's a complete scoundrel. This may or may not have been what attracted Eileen Prince to Tobias Snape, who is most certainly a bad man. Averted with Lily, who hates James' bullying and is weary of Snape's growing interest in the Dark Arts.
42* ''FanFic/{{crawlersout}}'': Played straight ''and'' inverted. Fem!Harry has no interest in romance currently, but she is set to become an OfficialCouple with her current ward, Tom Riddle Jr. (who will always be a bad boy even if he doesn't become evil). Then there's Gellert Grindelwald, of whom she is both charmed and repulsed by. In turn, both Grindelwald and Voldemort (prior to his death) have/had [[VillainousCrush Villainous Crushes]] on Harry.
43* During the embarrassing secrets challenge in ''Fanfic/TotalDramaEverything'', after [[Anime/YuGiOh5Ds Yusei]] admits to having a huge criminal record, [[VideoGame/UmJammerLammy Lammy]], who [[ShipTease was already crushing on him]], claims that just made her like him even more
44* Creator/CoeurAlAran's ''Fanfic/DatingWhatDaddyHatesRWBY'': Discussed. Several women at the resort are interested in Sun, a Faunus, who seems like a rugged bad-boy who might have connections to the White Fang terrorist organization. Likewise, everyone assumes that Weiss is only dating him as a fling for that reason. The truth is that Sun is just a big old goofball who has no love for the White Fang and is hoping for a serious, committed relationship. But because he's a Faunus, [[FantasticRacism everyone assumes the worst]].
45* ''Fanfic/ServiceWithASmile'': PlayedForLaughs. Roman Torchwick, an infamous and flamboyant criminal known for his crimes throughout the city, claims to have won actual competitions for "Vale's Most Eligible Bachelor."
46* ''WebVideo/VisionOfEscaflowneAbridged'': [[GenreSavvy Hitomi]] points this out to [[WrongGenreSavvy Van]] when has trouble being angsty over his [[CainAndAbel evil brother]].
47-->'''Van:''' He's still my brother no matter what he does!
48-->'''Hitomi:''' Wow, Van, that's actually a really mature and well-adjusted way to look at it...
49-->'''Van:''' Hey, thanks!
50-->'''Hitomi:''' ...And do you know how many fangirls mature, well-adjusted characters usually get?
51-->'''Van:''' Fifty thousand!
52-->'''Hitomi:''' Lower.
53-->'''Van:''' Five hundred?
54-->'''Hitomi:''' ''Lower''.
55-->'''Van:''' Square root of negative one?
56-->'''Hitomi:''' ...Okay, higher and...less imaginary.
57-->'''Van:''' ...Zero?
58-->'''Hitomi:''' Bingo! Now, angst! Angst like you've never angsted before!
59* In ''FanFic/TeenageMutantNinjaTurtlesVengeanceOfTheFootClan'', Jess has a crush on Mako, a delinquent at her school who is revealed in the fic's sequel, ''War of the Heart of Darkness'', to be [[spoiler:a member of the Purple Dragons]].
60* ''Fanfic/TotalDramaAllStarsRewrite'': [[PlayingWithATrope Played With]] in regards to Gwen and Duncan's relationship.
61** Gwen does like how hot Duncan looks in leather [[spoiler:and the ClusterFBomb he delivers to Mal in the final challenge]], but she also appreciates and tries to encourage his better qualities.
62** Duncan expresses concern that Gwen is losing interest in him and becoming increasingly attracted to the EvilerThanThou Alejandro (due to his belief he's losing his bad-boy edge and Alejandro charming Gwen earlier). When he asks her about it, Gwen makes it clear she finds Alejandro's evilness repulsive and is certainly not going to dump Duncan just for being nice.
63* It happens in ''Fanfic/XMenTheEarlyYears''. Before meeting Scott, Jean feels her interest piqued when her older sister advises her to avoid Scott Summers because he's trouble. Scott later notes Jean likes "bad boys".
64* Deconstructed in ''[[https://archiveofourown.org/works/32058559/chapters/79415632 MonsterPop 2]]''. Susanne and her friends are revealed to just be pawns of the evil people they choose to pursue.
65* Subverted with Tsubaki regarding Jin in ''Fanfic/BlazBlueAlternativeRemnant''. While she obviously pines for him, she's just as put off by his arrogant, cold-hearted attitude as everyone else is. She tends to call him out on his faults and tries to help him overcome them.
66* ''Fanfic/YouDontTakeShitFromAnyDemonsOrAngels'': Like in canon, Niffty prefers "bad boys" and that includes Adam.

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