Darth Bane: Rule of Two: Sort of... Zannah takes up a relationship with a terrorist she's manipulating, which is noted to be partly motivated by the fact being a Sith Lord in training doesn't provide a teenage girl with an abundance of warmth and affection. Not that she wants those things either, since she is fully on the side of Sith. And that means she's far more "bad" than her lover could ever be.
Oksa Pollock: The heroine Oksa Pollock falls in love in a bad boy called Tugdual.
In The Outsiders, Cherry Valence is afraid of Dally, the worst delinquent in the Greasers' gang, because she knows that he's the type of guy she might fall in love with.
Secret Santa (2007): Popular girl Celia has a big crush on motorcycle-riding troublemaker Jake Morrissey.
Anthony Trollope uses this in several of his novels. The most well-known is probably in the Palliser series, where Lady Glencora falls in love with ne'er-do-well Burgo Fitzgerald, leading her guardians to arrange a marriage between her and stodgy Plantagenet Palliser. However, at least three other novels have a wealthy refined girl fall in love with a rogue.
Vorkosigan Saga: This trope is a point of contention in the romantic subplot running through Brothers in Arms, Mirror Dance and Memory. Elli Quinn is deeply in love with the marginally sane mercenary Admiral Miles Naismith and will leap at the chance to marry him, while the prospect of becoming the consort of Lord Vorkosigan of Barrayar horrifies her, even though she knows both men are one and the same. The twist is that Lord Vorkosigan's comparatively subdued public persona is the least of her problems with the latter fate (the phrase "Dirtball barely out of Feudalism" came up in response to the first marriage proposal).
In The Reynard Cycle, the Countess Persephone is clearly drawn to Reynard for this reason.
In War and Peace, Natasha is engaged to Good Boy Prince Andrei. But after Andrei puts the marriage off for a year to please his father, Natasha is seduced by Bad Boy Anatole, causing her to break off her engagement with Andrei and also to very nearly elope with Anatole. Though Anatole's plans are foiled, it does succeed in permanently wrecking Natasha's relationship with Andrei.
Deconstructed in Wuthering Heights; the all-consuming love between Catherine Earnshaw and brooding bad boy Heathcliff is intensely passionate, but it's also clearly depicted as being quite unhealthy for the two (not least because they're almost brother and sister) and intensely destructive. Especially because, when he is rejected in favor of another man, Heathcliff's response is to embark on a single-minded crusade of vengeance that ends with the ultimately-pointless ruination of not only both lovers, but almost everything and everyone else around them. Meanwhile, Catherine's marriage to the kind and loving Edgar Linton (whom she does not love) is described as being reasonably happy—at least until Heathcliff shows up. There's also Isabella Linton, who wanted a bad boy, married Heathcliff, and got what she wanted in spades...
Jane Eyre: It works out well for Jane and Mr. Rochester, probably because she doesn't marry him until after he's not as much of a Bad Boy.
Deconstruction in Clarissa, as the titular character gets sick and bored of Lovelace's bad traits extremely quickly and he ends up harming her very badly, ending in her suicide and his guilt-ridden, death-seeking personality.
The Tenant of Wildfell Hall: Helen Huntingdon (Graham), the heroine of Anne Brontë's novel, marries the libertine Arthur Huntingdon, in part because she believes that she can save him from himself. She quickly discovers otherwise. In the process, Bronte makes some pointed jabs at both Heathcliff and Mr. Rochester. Anne Bronte had more experience of real life than her two elder sisters put together being the only one who could actually manage to hold down a job for more than a few months.
Zachary Gray, the thinking woman's Bad Boy, turns up in multiple Madeleine L'Engle novels.
The Changeover: Subtly deconstructed. The male character's initial behavior is not portrayed as being right, okay, or even wanted, and as he changes, the female lead becomes fonder of him.
The Dresden Files: Harry Dresden is very disappointed to find out his friend, Karrin Murphy, is like this when she becomes attracted to mercenary Kincaid in Blood Rites, and their thing continues into the next book, Dead Beat. Harry also realizes that Molly, his best friend's daughter, has these feelings for him—after all, he's the mysterious stranger in the duster who shows up out of nowhere, deals with dark things, and is the snarky badass to her dad's stodgy crusader. Harry then swiftly drives home that it won't be working like that. With some cold water.
Keep in mind that is all from Harry's perspective. We see clearly that Karrin's feelings for Harry run a lot deeper than she shows, in the short story told from her point of view after Changes. And they clearly aren't just "close friend" feelings, although they are close friends. And, the events at the end of Skin Game, well... So Jim Butcher zig-zagged this trope.
Hand of Mercy's Clemael's temper allows him to backhand a semi-disabled woman into the nearest wall, but said woman is oddly ambivalent as to whether she'll end up with him.
In the short story collection The Bloody Chamber by Angela Carter, Puss-in-Boots is well-aware of this trope and suggests that the best way to woo an unattainable woman is to: "convince her her orifice will be your salvation, and she's yours!"
In the Mexican novel El Zarco: The Blue-Eyed Bandit from Ignacio Manuel Altamirano, a beautiful young woman called Manuela is futilely courted by a nice, decent, and hard-working man called Nicolás, when, in reality, she is in love with the eponymous character, who is the leader of a notorious gang of murderous bandits called "Los Plateados". Later, she decides to run away with him, and it's then that she sees all the atrocities they commit.
In Taken at the Flood (1948), to the point where the heroine, Lynn, appears downright insane. She is engaged to Rowley, a simple farmer, but is attracted to newcomer David and his rudeness, aggression, and general ass-holery. However, when she goes to inform Rowley that she's going to elope with David, Rowley is so furious that he almost strangles her to death. When it turns out that David has been the real killer all along, Lynn resumes her engagement to Rowley, having been rather turned on by his murderous impulses. There's a good chance Christie is poking fun at this trope.
Young women like bad lots. They always have. They fall in love with bad lots. They are quite sure they can change them. And the nice, kind, steady, reliable husbands got the answer, in my young days, that one would be "a sister to them" which never satisfied them at all.
Another Christie character who fits into this trope is Patricia Fortescue from A Pocket Full of Rye who has married not just one but three different bad boys. Her first husband, Don, was a "arrogant, insubordinate" pilot who died in the Battle of Britain and whom she doesn't think could have handled peacetime. Her second husband was an aristocrat with an unsavoury reputation who committed suicide before the law could catch up with him. Her third husband was the Black Sheep of the wealthy Fortescue family at the heart of the book's plot. In fairness to Pat all three seem to have treated her beautifully.
In Parker Pyne Investigates, Mr. Parker Pyne advises a client who, on his honeymoon, has become entangled in events which make him seem worse than he is, that he should absolutely not tell his new wife the truth. "Your wife is a lovely and high minded girl and the only way she is going to get any fun out of being married to you is by thinking she's reformed a rake."
Iris falls head over heels for the charming and mysterious Anthony, though she senses an air of danger about him, his own point-of-view chapter reveals he has a criminal past, and many people are very worried he has his sights set on Iris's money. Subverted, he is revealed to be Good All Along (the criminal past was him infiltrating the saboteurs' organization he hunted down), he really adores Iris and he doesn't care for the money.
Victor Drake, who freely admits to never earning money honestly, is incredibly attractive, and even the proper and level-headed Ruth Lessing admits to feeling his charm. So much that she falls deeply in love with him, and he easily manipulates her to commit murder.
Even Death Comes as the End joins in on it (despite being set in 2000 BC Egypt), with Esa claiming much of Satipy's bitter henpecking of her husband Yahmose comes from his being so submissive to her and his father. Then subverted once Satipy catches Yahmose in the act of murdering his father's concubine: from that moment on she's a broken, terrified woman.
In the Sherlock Holmes story "The Illustrious Client", the Bad Boy in question is an aristocrat with a sulfurous reputation, who's charmed the girl into denying all allegations of misconduct on his part as jealousy and slander. His disfigurement by an ex doesn't help, as it only seems to prove that interpretation right. Holmes snaps her out of it in the end by bringing her a diary the man kept of his sexual conquests.
Rachel from The Hollows is subject to this trope time and again.
Dulcinea Anwin from Tad Williams' Otherland would like to be a Bad Girl. She's a Cracker, considers herself a seasoned veteran of the criminal underground, and has been lacking in physical company for a while now. Then she meets John Dread, who is baddest of the bad. So what should she do but fall in love with him and follow him around, sinking deeper and deeper into his web? After all, how bad can he really be, right? Until she manages to hack into his system and find out whathe'sreally like. At which point, she has a Heroic BSoD and tries to turn him in, only to be shot in the stomach and left to die.
Addressed and subverted in Gaston Lerouxs The Phantom of the Opera, with Raoul the childhood sweetheart of the Haunted Heroine Christine, jealousy accuses her of loving the eponymous Phantom aka Erik for (in his own words) being a dangerous and dashing rogue who builds a palace underneath the Opera House. Except as Christine makes abundantly clear to Raoul, shes utterly terrified of Erik and while admittedly captivated by his musical genius and feels great pity for him, she certainly cant look past his evil actions and controlling obsession with her - even initially trying to kill herself when Erik tries to force her to marry him. Christine also affirms that she would still choose Raoul, even if Erik was good looking rather than disfigured.
In Stephen King's Carrie (and the film adaptation), the Alpha Bitch Chris dates the bad-boy delinquent, Billy. The novel explains her attraction as Chris being used to wrapping boys round her little finger and Billy is the only boy she hasn't been able to control.
Sense and Sensibility has this, with Marianne having to choose between the somewhat shy, music-loving, thirty-five year-old Col. Brandon or the younger, dashing, and adventurous Willoughby. She, of course, chooses Willoughby, who eventually dumps her to marry some other girl for money, causing her to try to commit suicide by getting ill. Marianne eventually agrees to marry Col. Brandon.
Subverted in Making History by Stephen Fry; a quiet, shy college boy is set up on a date with a girl who eventually dumps him for the resident Jerk Jock. Except the quiet shy boy is actually gay and in the closet, and rather relieved that he doesn't have to keep up the awkward pretense of being interested in her.
Daenerys swoons over the dashing bad boy Daario even though she realizes that he's a murderous, opportunistic sellsword. On the other hand, she repeatedly fends off the advances of her devoted and loyal bodyguard Jorah because he's middle-aged, plain and not particularly exciting. (Then again, he's also a slaver who creepily feels Dany up without her permission, as well as spying on her, so it's more a case of Nice Guys Finish Last.) It's played straight with Quentyn Martell, though, with Barristan even narrating how young girls will always pick the exciting and dangerous fire over the Boring, but Practical mud.
There's a bit of a deconstruction here, as during the time in question Daenerys is stuck between trying to be a nurturer or a conqueror. She is attracted to people who can be her destructive Id for her, and ultimately rejects Quentyn when he proves unwilling/unable to master her dragons and be the destructive force she wants. Ultimately, by the end of the book she has decided to give in to her dark side and become a conqueror herself without using surrogate men instead: "Dragons plant no trees". The final books will show whether she can be brought back from this and/or have a relationship with someone who is not destructive.
Averted with Sansa. While she initially wanted Joffrey, who is verybad, she was initially blind to his flaws and thought of him as a heroic prince. However, though to be her ideal man one has to be a Princely Young Man or Knight in Shining Armor, she later develops attraction to Joffrey's bodyguard who is best described as The Brute (his first major action on pages is killing a thirteen years old boy) and seems to find his "ferocity" thrilling.
The Carrie and Bone subplot of Ander Monson's Other Electricities plays with this, going into detail about Carrie's motivations for wanting Bone, the community's reaction, and the tragic results.
In Shanna Swendson's Enchanted, Inc., Katie muses on this trope when she sees how powerful Owen is, and how attractive it makes him. She's never been attracted to bad boys, but maybe the thrill is the dangerousness, not the actual evil; she explicitly wonders if the potential is enough or you have to do actual bad things to qualify as a bad boy.
The landlord's daughter, Bess, from Alfred Noyes' poem The Highwayman has a Star-Crossed Lovers relationship with the titular character. Downplayed as he's utterly devoted to her, despite his dodgy occupation.
In Death: Eve and Roarke's relationship seems to be this. Fortunately, he returns her feelings and does have good qualities to go with the bad. Coltraine and Alex Ricker had a relationship like this, but she broke it off when she realized that he considered his criminal business more important than her.
Sisterhood Series by Fern Michaels: in the book Final Justice, two characters are introduced, and their names are Little Fish and Stu Franklin. Both of them are genuine bad boys. Countess Anne de Silva forms a relationship with Little Fish, and Isabelle Flanders forms a relationship with Stu Franklin. By the book Cross Roads, however, it becomes painfully clear that both relationships are falling apart, because Little Fish and Stu Franklin are becoming increasingly cold, distant, and disinterested in their girlfriends. The Vigilantes discover that the two men are with Henry "Hank" Jellicoe. They also find out that the two men are cold-blooded murderers who have killed a number of people. The Vigilantes are more than happy to have them punished!
Carol Birch's theory about Margaret Catchpole, the real-life eighteenth-century servant-turned-criminal, in Scapegallows. Margaret spends the entire novel pining over her beloved, William Laud, a smuggler who is terrible with money, increasingly violent, and often absent. Even she occasionally recognizes that he's not worth the effort.
This trope is discussed a overall three times in the novel Youth in Sexual Ecstasy, first with the protagonist and his friends when they notice that while women tend to fall over the rough-looking dangerous types, ultimately what wins out is being considerate, treating them "like a lady" and sweet-talking (all of which may or may not be sincere), later the doctor in sexual dysfunctions outright denies it, and then the protagonist's mother admits that there is a grain of truth in the trope as she experienced it on her youth.
In the Jeeves and Wooster story "The Spot of Art", Bertie lampshades this trope with regard to his romantic rival, who, sure enough, ends up engaged to the girl by the end of the story.
"Moreover, this bloke is one of those strong, masterful men. He treats Gwladys as if she were less than the dust beneath his taxi wheels. He criticizes her hats and says nasty things about her chiaroscuro. For some reason, I've often noticed, this always seems to fascinate girls, and it has sometimes occurred to me that, being myself more the parfait gentle knight, if you know what I mean, I am in grave danger of getting the short end."
Averted in all stories where Bertie is pursued by women who are very attracted to his gentle knight personality, and has to rely on Jeeves to get rid of his admirers without having to openly reject them.
Jay in the Spaceforce series is a compulsive womanizer and all-round Manipulative Bastard in a society where such behaviour is actually illegal, not merely amoral. He has no difficulty drawing women to him, both of his own species (Taysan) and alien—including Ashlenn, heiress to a clan chiefdom, who gives up everything to be with him.
At the end of The Legend of Sleepy Hollow, Katrina van Tassel (the girl schoolteacher Ichabod Crane falls in love with) ends up marrying hunter Brom Bones (who constantly made fun of Ichabod) after Ichabod was mysteriously carried off by the Headless Horseman one night.
Edward is this for Bella in Twilight. However "soft" he is as a vampire, he is still a brooding predator who could kill her in seconds and often wants to. She prefers him to the good ol' boy Jacob until Jacob takes a change for the dangerous—then she's conflicted.
Trapped on Draconica: Discussed by Ben: "Girls are all the same: you claim to like Nice Guys but you can't resist a bad boy." Defied by Daniar, who honestly can't stand them.
Ultimately averted in the Beka Cooper books. Beka Cooper, a cop, is friends with Rosto the Piper, the head of organized crime in Corus. They are attracted to each other and Rosto flirts with Beka, and he's the honorable kind of thief, but "he is a rusher, a criminal, the kind of man she has sworn never to involve herself with." Word Of Godholds that the Dating Catwoman thing just wouldn't have worked in this case. The man she does eventually marry is a Kennel mage.
Played with in the book Losers in Space by John Barnes. Both Susan and Emerald have relationships with Derlock, who's described as a sociopath. Susan doesn't love him and knows he's unfixable—she just thinks he's hot, which, while that's partially because he scares her a little bit, does not extend to any illusions of it being okay or her being special to him. As soon as things go bad with their ship, she realizes he's probably going to be as much if not more of a problem than their Space Isolation Horror issues, and quits sleeping with him. Emerald, on the other hand, is a more straightforward example, despite her original protests that she's also only in it for the sex. It...doesn't turn out well for her.
Will constantly says he's always out drinking and gambling, and that there are a dozen girls who've claimed that he'd compromised their virtue. Jem, however, thinks he's lying to make himself look bad.
Penryn: "You're not Fallen, are you?" Raffe: "From what I've heard, that would just make me sexier to you Daughters of Men."
Inna from Vampire Academy, is the willing servant and love interest of Nathan, a handsome Strigoi. Her love interest happens to be evil.
Subverted in A Brother's Price - some women are attracted to bad boys with good looks, much to the chagrin of their wiser sisters, who will have to share the same husband. Keifer Porter is one horrific example of what happens when the warning of a sister is not heeded.
Defied in Year Of The Griffin: Both Calette and Elda find Bad Griffin Jessak extremely sexy...but since they are both part-human and sentient, they both deliberately ignore being turned on and focus on how much of a jerk he is.
Christian Grey from Fifty Shades of Grey is into BDSM and has the typical personality of the bad boy/alpha male in romance novels: domineering, impatient, frequently angry, and demands to have his own way. Almost all women in the series are attracted to him who aren't related or lesbians. However, Ana alternates between believing that these are minor quirks and thinking that she can heal him emotionally by giving him everything he wants, thus healing him with the power of her love. Although Ana insists throughout the series (and with ever-increasing strength) that Grey is making progress and is maturing emotionally because of her, he actually becomes crueller and more controlling as the series continues, to the point where he tortures her against her will in Fifty Shades Freed. Her crime? Getting home later than she said she would and thus avoiding being kidnapped.
In Eden Green, the title character's best friend is infected with an alien needle symbiote by an edgy, misogynistic loner, and immediately makes him her new boyfriend. She's also revealed to have had a history of bad and even abusive relationships.
Amusingly lampshaded in the first novel of the Wolf Rampant series by Aimee Easterling. The protagonist Terra has a "moment" with another male character other than the love interest who happens to be a handsome, charismatic, and all around nice guy. She wistfully notes that it will likely go nowhere because she's too stuck on the bad boys.
In The White Rabbit Chronicles, Alice wants to date Cole even after Kat tells her that he's dangerous and not somebody to hang out with. Of course, having a vision of them kissing might have some influence.
In Rogue Star, Molly Zaldiver falls for the rogueish, brooding loner and rebel, Cliff Hawk, rather than the earnest, well-intentioned, and well-behaved Andy Quamodian who is hopelessly in love with her.
The Stormlight Archive: Of a sort. After their time in the chasms, Shallan admits to herself that Kaladin's confidence and dangerous intensity are very attractive. In the end, she goes with Adolin instead, and Kaladin resolves not to pursue her.
James Potter seems to think in the lines of this trope during his Hogwarts years. He acted pretty much like a Jerk Jock, bullying other students, especially Snape, for no reason than to have fun and seemed to expect girls would like him for this. This is evident when he wonders why Lily rejects him. Fortunately, he grew out of this behavior in his final years at Hogwarts.
Rowling was actually concerned about how Draco Malfoy invoked this trope among teenage female readers and stressed multiple times Draco is not a Jerk with a Heart of Gold behind all of his bullying and prejudice.
In a rare homosexual example, Albus Dumbledore, as a teenager, fell for future Dark Lord Gellert Grindelwald. While charming, Grindelwald was not like Tom Riddle and didn't even try to pretend to be a saint — by the time he and Dumbledore met, he had already been expelled from Durmstrang for experimenting with the Dark Arts in a ways that even they found to be "twisted".
Although a good deal of his modern fan-base might have its origins in this trope, Mr. Darcy in Pride and Prejudice is actually a subversion. In addition to his wealth and good looks, he's also aloof, curt, brooding and surly... and everyone around him except for his close friends consequently views him as a rude, arrogant dick and cannot stand him. Elizabeth Bennet initially hates him specifically because he said some very rude things about her, and when he delivers his initial Anguished Declaration of Love her response is to angrily reject him on the grounds that he's insulted her and her entire family, sabotaged her sister's relationship with his best friend, and basically never acted like anything other than, well, an aloof, curt, brooding and surly jerk. It's only when she learns that he actually does have a nicer side to his personality that Elizabeth starts to warm to him, and at the end Darcy openly admits that her criticisms of him were fair and he had to do a lot of soul-searching and improving of his character.
Zig-zagged in The Expert On Womens Hearts by Arkady Averchenko in the sense that there are different sorts of "bad". Evdokia Sergeevna says she told her daughter Lidia that the latters boyfriend Mastakov is a spendthrift, a womanizer and a gambler. Max tells her that it is the worst way to break up a couple, as the only result is that Lidia falls even more in love. Max himself takes a completely different route: he tells Lidia that Mastakov is awfully mean about money and that no woman wants to look at him because he never washes himself and at the same time Max claims that Mastakov is his best and dearest friend and has a crystal-clear soul. After that, Lidia instantly breaks up with Mastakov.
Lord Byron, "Mad, bad, and dangerous to know" personified this ideal for half of Europe.
The heroine of Market of Monsters frequently ponders this phenomenon after falling for a zannie — an "unnatural" human who feeds on human pain and gets his food by subjecting victims to Cold-Blooded Torture. She has no fantasy of "reforming" him, and she doesn't feel special or powerful about being one of the people he would never hurt, but she does admire his gift for torturing their enemies and wonders why, if the maxim is true, all girls they encounter instinctively avoid him in fear.
The Arts of Dark and Light has a somewhat downplayed example, with the heroine Fjotra finds herself somewhat attracted to the Red Prince due to his handsomeness and dark charisma, even though he is a villain and it's clear he intends to annex and oppress her country.
In Dogs Don't Talk, Ben wonders if this is why his douchey wrestling teammate Blake Barker is so popular with girls.
Deconstructed with Andrea's attraction to the arrogant and roguish Rob in Daddy's Little Girl, given he was indicated to be a controlling boyfriend and was convicted of murdering her. Ellie got the impression that Andrea was afraid of Rob, which was why she agreed to meet him the night she died to try and placate him after she'd agreed to go to a dance with another boy.