Although it's unexpected, there are plenty of instances when an anime villain falls in love with a hero in their series. People often say that opposites attract. However, all of these one-sided relationships are doomed from the very beginning of their conception for one reason or another.
The following eight entries in this list are canon in at least one part of the story, although there are instances where it doesn't last forever. It's a separate matter from fanon ships, which are not included in this article for obvious reasons.
Note: Hero, in this case, doesn't always mean the main protagonist. It simply refers to the characters on the protagonist's side.
8 anime villains who wanted to get with the hero (either out of love or lust)
1) Himiko Toga (My Hero Academia)
The most famous modern example of a villain falling in love with a hero is Himiko Toga from My Hero Academia. She's a prime example of a yandere who develops feelings for the main protagonist. It was just a one-sided obsession, which is a common trope for many of the entries on this list.
She even had feelings for Uraraka, another hero within the series. However, Toga's feelings toward both characters fade once her ideology clashes with the two heroes' own beliefs. Such a relationship was obviously never meant to be, and Toga just saw those two characters like she saw her parents at that point (aka people she would be fine with killing).
2) Esdeath (Akame ga Kill)
At first glance, one wouldn't assume that Esdeath has a feminine side to her. She's absolutely vicious and a complete social Darwinist. Hence, it's almost kind of random to see her swoon for Tatsumi in this anime. It's almost as if it's two completely different characters, especially since Akame ga Kill isn't a romance anime.
Still, she's completely obsessed with Tatsumi, and this relationship turns hostile due to the nature of this anime. Esdeath had a ton of power over Tatsumi during his brief time with her, but she failed to get him to love her like the other villains on this list.
3) Toneri Ōtsutsuki (Naruto)
Hinata is one of the most popular women in Naruto, so it's not surprising that at least one villain would fall in love with her. In this case, Toneri was a villain from the movie, The Last: Naruto the Movie who was jealous of Naruto's relationship with Hinata. Surprisingly, this is also a canon movie.
The Last: Naruto the Movie explores Naruto and Hinata's relationship in a sweet way, which really contrasts with Toneri's idea of forcing Hinata into a marriage. He predictably fails in the end and decides to atone for his sins on the moon, while Hinata and Naruto continue to love one another.
4) The Bear King (One Piece)
Nami is One Piece's most iconic female character, which inevitably leads to several characters falling in love with her. The Bear King comes from a non-canon movie known as Clockwork Island Adventure, wherein he is the main villain and serves as a tyrant of Clockwork Island.
He tries to force Nami into marrying him, but Sanji and the rest of the Straw Hats predictably stop that from happening. Outside of The Bear King, Absalom is another noteworthy One Piece character who lusted after Nami in the anime.
5) Midari (Kakegurui)
Midari has yandere-like tendencies, but instead of wanting to hurt others, she would rather be hurt or killed by somebody she's obsessed about. In this case, she's utterly enamored with the main protagonist, Yumeko Jabami. In a show all about gambling, there is no character who loves to take risks more than Yumeko.
Considering that Midari denied her that chance when they first gambled, it resulted in Yumeko giving Midari the cold shoulder whenever the two would meet up. Even if Midari gets ignored by Yumeko, she's still more than willing to try and get recognition from her within Kakegurui.
6) Giles de Rais (Fate/Zero)
Some people might know him as Caster. Regardless of his alias, he's in love with Jeanne D'Arc and is a villain in this anime. He is even under the delusional belief that Saber (Artoria Pendragon) is Jeanne and makes it his mission to make her accept that persona. Jeanne and Artoria are two completely different characters, but both are considered heroes in the context of the Fate series.
It's not hard to see why Giles would like somebody like Jeanne, but his sadistic tendencies make him arguably the least sympathetic villain on this list, which is only exacerbated by his strange design.
7) Prince Demande (Sailor Moon)
Demande does genuinely love Sailor Moon as a person, but his actions are reminiscent of those of a villain. He wants world domination with Usagi by his side and even wants to kiss her. Some parts of that are classic anime villain-y, but what makes Demande more interesting is that in Sailor Moon Crystal, he tries to protect Usagi.
Various Sailor Moon animes and mangas portray him differently, but the consistent part is that he harbors some feelings toward the main hero of the series. He did kidnap her and try to corrupt her, so there's still a vocal part of the fanbase that doesn't like him.
On a related note, he is actually a rare example of a male yandere in anime.
8) Onigumo (Inuyasha)
Another popular classic example of an anime villain falling in love with a hero is Onigumo from Inuyasha. Basically, Oniguno was a random bandit who allowed some yōkai to eat his body so he could become Naraku. His heart in this form still loves Kikyō, a good priestess who saved him back when he was Onigumo.
Unfortunately, Naraku kills Kikyō in the end, even though his human heart tries to stop him. He technically kills her twice, which makes the whole situation for Onigumo somewhat awkward, given his love for this priestess.
Note: This article reflects the writer's personal views.
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