In most anime, the lines between heroes and villains are easily drawn and rarely blurred. Both sides clash in climatic battles, with the former usually claiming victory over the latter sooner or later. However, there have been many instances of forbidden love where characters from both sides will become smitten with one another.
These rare romances are especially beautiful when considering the adversity they must overcome and the different worlds they are part of. These romances highlight anime's surprisingly compelling nuance, moral complexities, and interpretations of love.
Update by Alexandra Locke on February 24. 2023: Romance can spring forth from many places – particularly in anime. However, not-often-seen pairings between heroes and villains are always intriguing. Although some of these romances are one-sided, they are nevertheless entertaining. Hero and villain romances challenge viewers with their moral dichotomy and enthrall them with their often intense romances.
15 Esdeath & Tatsumi (Akame Ga Kill!)
Esdeath was the empire's most fearsome general in Akame Ga Kill!. She crushed foreign nations and subjugated their people with little empathy for the lives she ruined. After Tatsumi won her tournament of strength, Esdeath immediately became endeared to him.
She found his attempts to leave cute and did not take personal offense. The general became so fond of her new "boyfriend" that she overlooked his position as a Night Raid rebel and helped to protect him from the empire's wrath when necessary.
14 Beryl & Endymion (Sailor Moon)
As two people of noble birth in the Kingdom of Earth, Beryl and Endymion were often paired together. Throughout her life, Beryl harbored a secret crush on the prince and hoped to marry him one day. However, her dreams were smashed when Endymion met the Moon Kingdom’s, Princess Serenity.
Blinded by rage, Beryl led an attack on the prince and Moon Princess, killing everyone. Yet, when she went to strike the final blow against Serenity, she ended up killing Endymion instead. The trio is reincarnated years later in Sailor Moon, but the result is the same – proving that Beryl would have been better off keeping her feelings hidden from afar.
13 Toga & Deku (My Hero Academia)
Despite numerous attempts to attack him, Toga was surprisingly smitten with Deku. Although her affection was not reciprocated, she went to more lengths to be with him than any other character of My Hero Academia.
One of her greatest ploys was when she drained Uraraka's blood. She knew about Deku's infatuation with her, so stealing her identity proved to be a great tactical decision. Toga was forced to use Uraraka again to fend off Re-Destro's forces in the Meta Liberation arc.
12 Mai & Joey (Yu-Gi-Oh!)
Mai Valentine was one of the first major challenges Joey faced in Yu-Gi-Oh!. Her harpy-based deck proved a serious challenge for his straightforward cards, especially since she cheated by lacing them with unique perfumes. Despite Mai's ego, the events of Duelist Island sparked interest between the two of them.
When Marik defeated her on the airship, Joey was particularly devastated. Mai may have been self-absorbed and manipulative, though she did not deserve the Penalty Game that the villain forced her to live through using his Millennium Rod.
11 Yukiteru Amano & Yuno Gasai (Future Diary)
Yukiteru Amano finds himself embroiled in a despicable battle to become a god in the anime, Future Diary. However, little does he know that the most harrowing thing he will encounter is one of the other contestants and his eventual love interest, Yuno Gasai.
Yuno’s obsessive affection for Yuki works to his advantage for most of the game. Her monstrously protective instincts come in handy when other players try to attack Yuki. Unfortunately, when there are only a few players left, tensions start to rise, and Yuno discovers the truth of Yuki’s attachment to her. Yuno and Yuki are a villainous and heroic duo that should have thought twice before entering a relationship.
10 Shigure & Akito Sohma (Fruits Basket)
Fruits Basket is full of relationships that many would consider unhealthy, but arguably the most unhealthy relationship is between Shigure and Akito Sohma. Although Akito has abused many of the Zodiac members for years, Shigure still loves her. However, he also makes her jealous on purpose as a form of punishment – which only causes her to lash out more.
Shigure is often seen as a hero – or at least a nice guy – at the beginning of the story for taking Tohru Honda in, but he has many toxic traits that are anything but heroic. Even so, Shigure and Akito make a poisonous hero and villain pair that deserve each other for their despicableness.
9 Yukako & Koichi (JoJo's Bizarre Adventure)
At first, Yukako was one of the evilest characters in JoJo's Bizarre Adventure. She became so fixated on Koichi that she abducted and tortured him all in the name of love. Although Koichi escaped his stalker's clutches, he did not punish her for attempting to ruin his life.
With her first plan failing, Yukako consulted Aya Tsuji and made her use the Cinderella Stand to make Koichi love her. Considering that they became a couple by the end of the series, this plan was surprisingly effective.
8 Sasame & Takako (Prétear)
As one of the Leafe Knights, Sasame is sworn to protect the Prétear. Unfortunately, he could not save his beloved Takako from herself, and she became the Princess of Disaster.
Years later, a new Prétear is discovered, but nothing can keep Takako from Sasame’s mind. His love for her is so great that he even turns his back on his comrades to become Takako’s henchman. Fortunately, the two are eventually saved thanks to Himeno’s White Prétear transformation, and everyone has a happy ending at the end of the anime Prétear.
7 Lisa & Vulcan (Fire Force)
Fire Force's Lisa was a White-Clad spy sent to seduce Vulcan and convince him to share his plans. Over time, he grew to trust her, and her manipulative ploy proved a smashing success.
However, Vulcan did not give up on her even after Giovanni made her allegiances clear. He stormed the Nether alongside Company Eight, rescued Lisa from the abusive cult, and vowed to continuously protect her regardless of how she had already wronged him. Although reticent at first, the love Lisa once faked for Vulcan quickly became more genuine than she believed possible.
6 Ohgi & Villetta (Code Geass)
When Ohgi and Villetta first fall for each other in Code Geass, neither knows of the other's true identity. Since Villetta suffers from amnesia, she does not identify Ohgi as an enemy that needs to be dealt with.
After regaining her memories, Villetta feels apprehensive toward Ohgi and accuses him of using her. Regardless, the memories they made beforehand were still very real, and it does not take long for them to fall in love again despite their diverging life paths. Their love story is Code Geass's most underrated subplot.
5 Pudding & Sanji (One Piece)
At first, Pudding assumes Sanji would find her third eye hideous, which she uses as a justification for killing him. However, when he comments on its beauty, it immediately shatters her will to take his life.
Although Pudding still occasionally flirts with selling Sanji out to Big Mom, she becomes one of the Straw Hats' greatest allies when escaping Whole Cake Island. Unfortunately, since Sanji had yet to find the All Blue, he could not settle down with her and pursue the love he often dreams about. Regardless, Pudding is the closest thing Sanji has to a real partner in One Piece.
4 Yoshikage Kira & Shinobu (JoJo's Bizarre Adventure)
As a prolific serial killer, Yoshikage Kira initially views Shinobu as a tool to be exploited. He wants her to remain content so that no one will investigate his new identity. However, when Stray Cat attacks her, Yoshikage Kira feels a genuine urge to protect Shinobu even at the risk of his own safety.
He convinces himself that her death will spark suspicion, though he ultimately never moves against her. Since Shinobu never learns about what happened to Kira, her fate is one of the greatest tragedies of the series.
3 Fudoh & Demisu (Love After World Domination)
Love After World Domination follows Fudoh Aikawa and Desumi Magahara who are trying to keep their relationship a secret at all costs. As members of opposing factions, Red Gelato and Reaper Princess must do whatever it takes to temper their feelings in battle.
Even though the Gelato 5 and Gekko fight incessantly, Fudoh and Desumi always find time to be together. Their love in an endearing, yet tricky, tale of the lengths people will go to for love.
2 Mikasa Ackerman & Eren Yeager (Attack On Titan)
Initially, the relationship between Mikasa and Eren was unclear. Some felt like they were brother and sister, while others considered their relationship to be a blossoming romance. It took until the end of Attack On Titan for the latter to be proven true.
Even after Eren tells Mikasa he used her and wiped out eighty percent of the global population, she still shares a heartfelt kiss with him. However, it is particularly disturbing since she had been embracing his decapitated head. Mikasa's forbidden romance ranks among the series' greatest controversies.
1 Sakura & Sasuke (Naruto)
Since the beginning of Naruto, Sakura's only goal has been to be with Sasuke. She goes to great lengths to be with him, including risking her life and reputation on behalf of his unrequited affection.
There are multiple points where Sasuke is verbally or physically abusive, nearly even killing her by using his chidori. Given Sasuke's emotionally volatile state, Sakura should have listened to her many friends and colleagues who caution her against pursuing a relationship even if it ultimately works out in the end.