Though knowing Gauron, he probably loves it more that Kashim hates him and beats the shit out of him. Whenever Sousuke displays docile tendencies and sort of "gives in" (like in TSR, where he gently told Gauron "please"), Gauron gets pissed off and acts like it would've turned him on a lot more if Sousuke were acting violent and defiant.
Comedic example found in Girls Bravo. Yukinari, Kirie, and Koyomi are wanted by the perverted Lisa, Kosame, and Fukuyama. All the punches and various other acts of rejection they dish out? The Fukuyama siblings, plus Kosame, like it very much.
It can be argued that Rolo is like this in regards to Lelouch, who even flat out tells him at one point that he's simply using him.
And Mao displays even more clear indication of this for C.C. He is so completely in love with her that he thinks it's alright to cut her up with a chainsaw in order to run away with her.note Note: she's immortal, she would have survived, but it would still have been none too pleasant...
Outlaw Star: Melfina is terrified of Harry for his unhealthy obsession with her and wants nothing to do with him. Rather than drive him away, her rejection of him simply makes him even more determined to win her love. Which he somehow manages to do, shortly before he dies; why Melfina changes her mind all of a sudden when he makes it explicit that the only reason he's being even remotely respectful is that he's on his way out and doesn't have the energy to be his normal, creepy self is a mystery for the ages.
His sister Kodachi also partially qualifies for her pursuit of boy-type Ranma, but before the end of the manga admits that she knows he doesn't love her. Note that this doesn't actually stop her.
And of course, one must mention Mousse, who pursues Shampoo past all common sense...
And Shampoo, in her pursuit of Ranma.
Ryoga almost qualifies in his pursuit of Akane, he's just smart enough to hide it and take the stalker route instead.
Bleach: Nemu Kurotsuchi puts up with the abuse and humiliation of the sadistic Mayuri Kurotsuchi, her father, because of her love and admiration for him.
The quite, quite mad Misa Amane of Death Note will gladly do anything, including kill others or sacrifice herself, for Light's sake after he kills the murderers of her parents. Light sees her as an annoyance but one that can be easily manipulated, so he plays along, albeit considering killing her quite calmly at several points, although he never does it. After Light dies, she commits suicide according to Word of God, though a girl remarkably similar to her is seen participating in a candlelight vigil for Kira. Considering the blonde hair and the fact that she held a lucrative career before becoming the second Kira makes her seem like an anime version of Harley Quinn (especially considering Harley's new outfit in Batman: Arkham Asylum).
Yubel in Yu-Gi-Oh! GX is not above murder, manipulation, kidnapping, torture, and even brainwashing and assaulting its own love interest Judai so they could be together. In an unusual twist, Yubel also makes itself out to be the Love Martyr, encouraging Judai to do the same despicable things to it, under the crazed belief that since "true love" is sharing emotions and experiences - both good and bad - love can only be expressed through shared suffering.
The only one of the seven Sensui selves Itsuki seemed to think he had any romantic mileage with was the girl. Which, yeah. All of him liked having Itsuki around to help out, though.
Vampire Princess Miyu has Ranka the Uncanny Valley Girl and Shinma puppeteer, and Kei Yuzuki the Chick Magnet. He knows she's not from this world and that does not stop him from falling for her. And yes, she loves him back and takes him to the Darkness with her... at Kei's own request.
Haru towards Tsuna in Katekyo Hitman Reborn!. Interestingly, she started off hating Tsuna because she thought he was mistreating Reborn, but quickly changed her mind after he saved her from drowning. With a little help from a Dying Will Bullet, of course, but that was enough to rewrite him as "awesome" in her book.
Chrome for Mukuro. Of course Mukuro does seem to love her back in his own twisted way.
Russia beats and stalks Lithuania, the only person he seems to be truly happy around. Considering that Russia is a male Yandere... well.
His sister Belarus is quite similar. Lithuania seems to have a crush on her, she agrees to go out with him once... and ten minutes later, she breaks and twists his fingers. Then, she's shown as Russia'sStalker with a Crush... Must be In the Blood.
Belarus and Russia also qualify. He constantly cries, hides, and tells her to "go home!", but that doesn't stop her from literally breaking down his door wanting to "get married, married, married!"
They go take over Hell together afterward! It's sweet! (No, really. This happens. They wait for Hoji, his administrative assistant with a man-crush, to commit suicide and catch up with them, too.)
Kamatari had it even worse, though I don't think either case with Shishio really applies—he was quite happy to have them around, he's just All Take and No Give.
Kamatari had it even worse because he's a crossdresser and gay, though hardly gender-queer at all (he laughs and flashes Misao when she mistakes him for a woman), and is perfectly aware that he's not the strongest or the most beautiful retainer, and can't compete for Shishio's attention on either field. Even if Shishio liked guys, he'd still probably go for Soujiro. Ow, Brain Bleach please.
Fans theorize that Kamatari probably has a past in Kabuki as an onnagata somehow. Onnagata sometimes also worked as high-end call boys, for the right fans.
Shishio's good looks are utterly ruined by hideous full-body burn scars, but this doesn't appear to put off either admirer. Maybe that's because despite being horribly Covered with Scars (and he wasn't THAT bad-looking when in full shape), the dude is also damn smart and charismatic.
Ladd Russo and his fiance Lua in Baccano! share quite the odd romantic relationship, what with Ladd being a delightfully Ax-CrazyPsycho for Hire and Lua being an oddly serene masochist. To them, "I'll kill you last", means "I love you."
Specifically, "I'll kill you last" as in "I'm saving you for last because I'll enjoy killing you the most."
Yuno Gasai of Mirai Nikki. She'll do anything to be with her Yuki-kun. "Anything" including suicide, homicide (with an axe), stalking, etc.
When he told her he reciprocated her love, she responded by tying him to a chair and keeping him drugged, to ensure that he'd stay faithful.
It is worth noting that, despite being as reasonably sane as is humanly possible while also being capable of massacring orphans (It Makes Sense in Context), he's still with her after escaping from the chair.
In Black Cat, Creed is crazy about Train. Train constantly tries to beat him off of him, and attempts numerous times to kill him. And Creed just can't seem to take a hint. Train must be resisting because someone "evil" is influencing him... and that person must be killed.
Digimon: Mummymon is head over heels in love with fellow villian Arukenimon, even though she clearly isn't interested. Subverted somewhat in that neither of them are particularly crazy, and she's willing to tolerate him unless he gets too touchy-feely.
Sasame from Prétear wavers between this and Love Martyr. On one hand, he's genuinely selfless and wants to help the girl he loves. On the other hand, the girl he loves is a Dark Magical Girl that doesn't care about him, and he's willing to destroy the world to stay by her side.
Eva Heinemann from Monster 'fails to get the message' to the extent that her ultimatum to her love interest, after he rejects her very plainly, is the following: facing murder charges which she will lie through her teeth to corroborate, or being with her. That Tenma chooses the former is a good indicator of how batshit crazy she is.
More of an inversion though. Eva has no illusions that she is actually in love with Tenma; she only wants to be with him because her life went down the crapper after she dumped him for no good reason, only to realise much later after a string of bad boyfriends (one a homicidal lunatic) that Tenma was probably the only one who actually cared for her. Her rationale swings between a consciously doomed attempt to recapture that love, and more usually a resolution that, if she has to suffer, Tenma must suffer with her.
Hannah for Alois. No matter how much he hurts her, she wouldn't think of leaving him, since she absorbed Luka's love for him.
Also Grelle for Sebastian. Leaving the fact that she's a male-to-female Transsexual (coming from Word of God, and here's◊ the proof◊), she has a tendancy to do anthing to get Sebastian's attention. This makes her useful for the other main characters, especially Ciel, who promises her alone time with Sebastian in return for help. Sebastian does not seem too fond of this idea when he finds out, and as far as the anime shows, he manages to avoid her. Oh and did we mention she's a death god and Sebastian's a Demon? Yeah, this a very strange relationship indeed.
The fact that Knives doesn't care about him is sad. The fact that he is perfectly aware that after trying to have Vash killed any chance of Knives ever liking him is gone, is very sad. The fact that despite how shittily Knives treats him no one else ever treated him nearly as well is just tragic.
Like the Rurouni Kenshin example above, this Big Bad's minions include two who are madly in love with him. Also, much blood and horror, and Legato is totally unhinged for most of Maximum.
The trying-to-eat-a-steak-while-voluntarily-in-a-bondage-straitjacket thing was funny, though, in a horrible way.
Uh... wasn't that after Knives broke his spine for trying to Murder the Hypotenuse while Knives was in his healing vat?
Every single relationship in Durarara!! is like this, mostly due to the incredibly dysfunctional cast. The healthiest one is probably the relationship between a back-alley surgeon and a female Dullahan (that is, a woman with no head), where the former outright says that he dissembled about the location of the latter's head because he never wanted her to leave him. And that's the point where their relationship improves.
Prince Diamond and Ali towards Usagi in Sailor Moon and Emerald towards Prince Diamond.
Shuichi from Gravitation towards Yuki. He chases Yuki constantly, despite being rejected, verbally abused, and often being called a little brat. They eventually end up together.
Gintama: Ayame "Sa-chan" Sarutobi actually enjoys being abused/rejected by the object of her affection Gintoki.
Quite a few relationships in Pandora Hearts are like this, like Jack for Lacie, Oz for Alice, Vincent for Gil, possibly even Gil for Oz... Echo for Vincent looks like it's going to be a major one after the release of chapter 89.
In InuYasha, Inuyasha found himself on the receiving end of Jakotsu's attentions who was quite determined to show Inuyasha the affection he always gives to his favourites... which involves death and possibly torture/rape.
Harley Quinn and Joker. The one shot comic Mad Love, which was later adapted into an episode of the same name, that tells how Dr. Harleen Quinzel, then a psychiatrist at Arkham Asylum, first met The Joker. The Joker saw her immediately as a tool to be used, and manipulated her into becoming a henchmen. However, at the climax, Joker tosses Harley out a 3rd story window for getting the upper-hand on Batman without him, and she blames herself because she "didn't get the joke". Cut to Arkham at the end of the episode with a heavily-bandaged Quinn vowing in her normal voice that her life of crime was over since she now saw the Joker for what he was: "a murderous, manipulative, irredeemable -" At which point she spots a rose sitting in her cell with a note of apology from Mr. J, causing her to smile and dreamily say "Angel!" in Harley's voice. Definitely chilling, and worth a watch. Even more so in the comic, Dr. Leeland asks Harley what it felt like to be treated so poorly after all she's done. Harley notices the rose and says "Like a kiss" which is all the more disturbing. (In fact, it's a Shout-Out to the 1962 The Crystals song, "He Hit Me (It Felt Like a Kiss)".) According to Bruce Timm, The Joker really does need her, saying, "Everyone's seen The Joker laugh. Harley is the only one who's seen him cry."
You can see it too, when she runs off with Ivy, the man can't even find his socks.
At one point, after yet another incident when the Joker nearly kills her, Ivy freaks out in frustration and demands to know if Harley understands what just happened, and Harley tells her that yes, she knows he was trying to kill her.
In Death Of The Family, Harley Quinn has gone back to the Joker's side, and she even set herself up as a convincing decoy for Batman to go after at the Ace Chemical Plant. Played with, turns out she's not there solely out of loyalty to the Joker (and even states that he's not her Mr. J any more, and outright attacks him); she's there because Joker threatened to desecrate Deadshot's corpse. Also, the Joker's mad that she got together with Deadshot, and it's one of two reasons he's going after her at all.
This seems to be Joker's motivation for his war on the Bat Family and Batman's rogues.
An old example from the funny pages occurs in Krazy Kat. The eponymous character has a crush on Ignatz Mouse, and regards the bricks he pelts at her as signs of affection: "Little dollink — always fetful!"
Mr. Gosh from Lenore the Cute Little Dead Girl takes Mad Love to a whole new level, as the eponymous Lenore frequently kills him in response to his interests—he incorrectly writes it off as more of her typical fatal accidents, when he's one of the few people she intentionally tries to kill. Then again, as Lenore is a 10-year-old girl who died roughly a century prior to the start of the comics, the Mad Love may be the least disturbed part of his interest in her.
In the newspaper comic strip Curtis, Curtis Wilkins considers the snobbish and aspiring actress Michelle to be "my girl," despite her going to great lengths to avoid him (and when she doesn't, it's only to brag to him about her accomplishments or have him do some menial task for her). Even after Michelle flat-out states to him that she's tried every way she can think of to show that she's not interested in him, Curtis believes that she's only being a good actress, causing her to sob in frustration.
Terra's and Beast Boy's relationship is hilariously flanderized into this in Tiny Titans. Beast Boy is head-over-heels in love with Terra, however Terra loathes him and his affections. It goes way past being annoyed at his love-sick behavior, she's constantly pelting him with rocks and berating him.
The Captain America villains Red Skull and Mother Night had a relationship like this. Mother Night was deeply in love with the Skull, even though he was always abusive to her. At one point he even started flirting with Viper (another Cap villain) just to piss her off.
Subverted in "The Acid Test," in issue #11 of The Haunt of Fear, when a woman threw acid in her slavishly devoted husband's face to discourage his attentions and he argued in court that it was done in the heat of the moment and he still loved her, only to reveal that it was all part of his plot for revenge and gloat about how, once he gave her the same treatment, she'd never leave him again...
Darkheart is obsessively in love with Discord in The Return Of Chaos. This probably owes rather a lot of inspiration to Harley and the Joker.
Many, many Harry Potter fanfictions portray Bellatrix Lestrange as feeling this way towards Voldemort, but Harry Potter and the Methods of Rationality is one of the few works to make all the awful treatment she endures because of it explicit rather than mere subtext. It is notPlayed for Laughs, and in fact firmly establishes Voldemort as irredeemably evil in Harry's mind when he realises that he can be presented with such fanatical, unconditional devotion and not love her back, not even a little bit.
BK Willis' "To Die For" series of Doctor Who fics features an Adric who's pretty much the equivalent of South Park's Kenny and a Nyssa who causes said deaths every time he tries to approach her in a romantic or even semi-friendly manner, played for black comedy.
Mrs. Lovett in Sweeney Todd: The Demon Barber of Fleet Street, who enables Sweeney's serial murders and disposes of his victims by baking them into pies. She continues to make romantic overtures to him despite his obvious disinterest, going so far as to trick him into thinking his wife is dead. He throws her into her own oven to burn to death when he discovers her deception.
The classic film Mad Love (a remake of the Conrad Veidt film Hands of Orlac) is a borderline case at best. Dr. Gogol loves the beautiful actress Yvonne, and knows she is happily married to her husband. He settles for trying to drive her husband mad in the hope of picking her up on the rebound.
Serves as The Reveal in He Loves Me... He Loves Me Not. For the first half of the film, we are led to believe that the main character is having an affair with a married man, but at the midway point the film snaps back to the beginning and follows the man instead. We find out that she is really an insane stalker and he barely knows she exists.
This is driven even FURTHER in the original play in which Columbia does a Heroic Sacrifice by putting herself between Frank and Riff Raff causing her to be killed by the laser. Frank's reaction? "Stupid bitch." Though, he does say it in a way that hints that he did feel somewhat sorry for her.
Bellatrix Lestrange in Harry Potter embodies this trope. She's as mad as they come, and her devotion to Voldemort is nothing short of obsessive.
In Second ApocalypseCnaiŁr develops a very twisted sort of love/obsession with SerwŽ who wants nothing to do with him, because he keeps raping her.
Wuthering Heights - Edgar for Cathy Earnshaw. She walks all over him, ignores his wishes, throws temper tantrums and obviously prefers the company of Heathcliff, and yet he refuses to give her up.
Live Action TV
In The Flash TV series, Mark Hamill's Trickster character was the reason he was considered for his later Joker role, it was very similar to the point of having his own Harley Quinn, an unstable thrill-addicted toy designer who calls herself Jinx:
Trickster: For me? Gee... after I treated you like dirt... hung you out to dry...
Jinx: I love you... madly.
Trickster: Oh, darling, it won't work. I'm no good for you. Besides, how can I miss you... when you won't go away?(pushes Jinx out of a moving vehicle)
Christian Troy and Kimber Henry on Nip/Tuck: in the very first episode, shortly after they've slept together, he strips her naked and covers her in red lipstick to mark the places where he thinks she could use a little surgical tweaking. She comes back. Enough said.
Oz: Chris Keller is all too willing to do anything to keep Beecher for himself, even though this is what drives Beecher away and eventually kills Keller. Their relationship is quite tragic and fucked up, to say the least.
True Blood: In "It Hurts Me Too" after Bill pins Lorena against a wall and tells her that he'll never love her, she kisses him. He does not react well to this, first going for her throat with his fangs, then responding to her urging him to make love to her by doing so extremely violently to the point that he leaves several cuts on her chest and twists her head around 180 degrees. Lorena loves every second of it, and dreamily says "Oh William, I so love you." Also, even after Bill tells Lorena multiple times that he hates her guts and can't stand the sight of her, she still has the nerve to ask him "When will we see each other again?"
Oh yes, you can kick me And you can punch me And you can break my face But you won't change the way I feel 'Cause I love you."
Muse's "Space Dementia" ("You make me sick/Because I adore you so"; "You make us wanna die/I cut your name in my heart/We'll destroy this world for you/I know you want me to/Feel your pain"). Pretty creepy.
Eminem and Rihanna's "Love the Way You Lie". Bonus points when you consider both were on different sides (giver and receiver respectfully,) in different Mad Love relationshipsthemselves.
See also "Love the Way You Lie Part 2," which is largely the same song, but told more from the opposing point of view.
Will Smith's "Loretta" is about a real-life stalker of his (supposedly).
In A Midsummer Night's Dream, Helena is this way about Demetrius, despite the fact that he repeatedly threatens her. Pretty soon, application of Love Potion makes both Demetrius and Lysander fall in love with Helena, which leads to her angrily fending off two guys, convinced that she's being made fun of. In the end, the spell on Lysander is reversed, and Demetrius and Helena get married.
Adaptations of the Public Domain character Sweeney Todd often portray Ms. Lovett in this manner. Musical adaptations almost always do so. Sweeney is rarely shown returning her affections. How crazy are they? One is a mass-murdering butcher who is still the Woobie of the plot in musicals, and the other packs the bodies into meat pies and sells them to unwitting customers.
The less-common male version occurs in Tales of Symphonia: Dawn of the New World with Alice and Decus, with the former utilizing the latter's feelings for all they're worth. Of course, that all changes when Decus sacrifices himself to save Alice...
It's hinted in Pokemon Diamond/Pearl/Platinum that Mars (and possibly Jupiter too) of Team Galactic are on the team due to an infatuation with Cyrus. Since Cyrus considers all emotion burdensome, you can guess how much he returns these feelings.
In Episode 3 of Phantasy Star Universe it is greatly implied that the reason Helga is so intent on serving Howzer, even after he deemed her as "expendable," is because she is in love with him.
Tira from the Soul Series is absolutely devoted to Nightmare. The scary thing is that this might be her least disturbing trait.
Shrowdy von Keifer, villain of A Vampyre Story, makes a habit of kidnapping young women and then "disposing" of them when he gets bored. By the time the storyline proper rolls around, Mona is but the latest in an ever growing line of women who have disappeared that way, and on top of that, she's either the woman Shrowdy's been looking for, or due to be axed at any minute, because she's lasted longer than any of her predecessors. Just for added creepy fun, it's very strongly implied that Shrowdy's victims are all chosen because they resemble his missing mother.
There are hints that Carmilla from the Castlevania series feels this way towards her master Dracula. Dracula seems to be indifferent, but Carmilla worships him and does everything in her power to aid him in leading humanity into darkness despite showing no true hatred towards humans.
Later in the series, we discover that the truth behind this is far worse: Man meets woman, they fall in love, man keeps woman as his mistress in a hidden mansion, they have a daughter but the woman dies, daughter grows up to look so much like her mother that her father forces himself on her, daughter becomes pregnant and has a child but dies not long after, man still spends most of his time screaming at the sky until he finally meets that lost child. And dies. And then that lost child becomes the secret master of the island and also becomes crazy because of love.
In Dangan Ronpa, Touko Fukawa has this kind of relationship with Byakuya Togami. Togami makes it clear several times that he doesn't think much of her (then again, he doesn't think much of anyone), but Fukawa just interpret his insults to mean that he's secretly concerned about her. Still, Togami isn't above taking advantage of Fukawa's almost slavish devotion towards him when he sees fit.
It's at least strongly hinted that Genocider Syo's murders were all motivated by her becoming infatuated with the victims, all 1000+ of them.
In Dra Koi the dragon falls for the protagonist, enrolls in his school, chases him around and rapes him on the roof and then moves in, after which he reluctantly enters a relationship with her. What else can he do?
The Pucca/Garu romance in the webcartoon and television cartoon Pucca has many elements of this, although in this case, it's not necessarily the love that's unrequited, just the interest in displays of affection. Garu does care for Pucca, but he's still not past the "Girls Have Cooties" stage and his girlfriend is a huge Clingy Jealous Girl.
Suicide for Hire has had a few of these, first with a crazed stalker who, upon realising she had over 9000 competitors for her target's love, decided to drag his reputation through the mud to ensure she was his only choice; then, later on, there was a woman, who even after having her scalp ripped off and her baby forcibly aborted, a la Jigsaw's wife, still goes back to her husband.
Justified in that the second woman was suffering from Domestic Abuse-induced Stockholm Syndrome - she knew she shouldn't go back to him, but he'd cut off every other contact in her life so that she couldn't see any means of successfully escaping him.
Harley Quinn and the Joker, again: All throughout Batman: The Animated Series (where Harley originated, after all), she loved him unconditionally and madly (in the insane way as well as deeply). She would quit him every so often and join up with Poison Ivy, but would go work for him again in the end. See Comic Books for the deconstruction about Harley's origins, which gives her Hidden Depths. (Harley was originally just a Mook du Jour but became an Ascended Extra.)
Batman Beyond had a similar case with the supervillainess Inque and a random sap named Aaron Herbst who supervised her while in prison. Aaron ends up requesting to be given shapeshifting powers like Inque, to which Inque responds by giving him only half the treatment, causing him to mutate into a liquedated, powerless blob, and in the end being on the receiving end of this trope.
Ed, Edd n Eddy has the Kanker Sisters extreme romantic pursuit of the Eds.
Pepe LePew from Looney Tunes. The clawing, the biting, the beatings, the screaming and running away? He's confident that the object of his desire is just "playing hard to get."
In a similar vein, there is also Fifi LeFume from Tiny Toon Adventures who chases after any potential skunk boyfriends (or more to the point, male dogs or cats that have white stripes down their back and were doused in black paint).
Speaking of Tiny Toon, how about Elmyra? One may think she certainly qualifies, though in a zoophiliac version of the trope.
Incidentally, those shorts that show how much of a spitfire an interested Penelope can be suggest that Pepe's scent is literally the only thing driving her away; sad, then, that Pepe is intimidated by assertive women and rapidly loses interest as soon as one or both of them does something to take his smell out of the equation.
Nathan Leopold, who was willing to engage in criminal acts of an escalating nature as long as Richard Loeb (who was more successful socially, better liked and better looking- as well as sociopathic) had sex with him.
Lynette Fromme served 34 years in prison (released August 2009) for trying to assassinate U.S. President Gerald Ford because she thought it would make Charles Manson happy.
In the Stephen Sondheim musical Assassins, during her part of a duet she croons "You are wind and devil and God/Charlie/take my blood and my body for your love/let me feel fire, let me drink poison/tell me to tear my heart in two/if that's what you want me to do..."
The documentary Crazy Love documents the real-life (and pathetic) Mad Love between Linda Riss and Burt Pagach. After the two had an affair (which Riss ended), Paguch hired men to throw lye in her face. He went to jail, but Riss dumped her fiance (who still wanted to be with her after the attack) and married Paguch after he got out. Certainly brings new meaning to the phrase "severe co-dependence".