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The usual storytelling tool in movies is to have two heroes fall for each other and start a relationship, regardless of whether it works out between them in the end or not. Another option is for two villains to get closer while they wreak havoc and make the heroes' lives more complicated. By far the least common scenario is when the hero falls for the villain.
Usually, they don't spend nearly enough time together to build a romantic bond and can be often too antagonistic to each other to get together. Yet there are some rare instances in movies where the hero liked the villain, and in some cases, they even dated for a while. It's important to point out that such relationships don't tend to last forever in movies.
6 Batman Returns (1992)
One of the most iconic comic book relationships is between Batman and Catwoman. Even though they often stand on the opposite side of the law, they still show rare understanding toward one another. Plus, they teamed up multiple times to save the day. In Batman Returns (1992), Michael Keaton's Bruce Wayne falls for Michelle Pfeiffer's Selina Kyle as they go on a few dates.
At the same time, Batman has several flirtatious encounters with Catwoman. When they realize who the other person was, Batman tries to persuade Catwoman to abandon her quest for revenge aimed at Max Schreck, but he fails. As a result, the two part ways, proving that sometimes the romance between a hero and a villain just can't work out.
5 Dracula (1992)
In the book Dracula by Bram Stoker, Dracula infects Mina with vampirism, and she helps her beloved Jonathan Harker, Professor Van Helsing, and others to defeat the powerful vampire once and for all. That's not what happens in this more romantic version of the story. Mina meets the charming Dracula and falls for him.
Even though he's responsible for the death of her best friend Lucy, Mina still forgave Dracula for his actions and helped him find peace by killing him. This love story doesn't have a typical romantic ending but at least Mina survived, which can't be said for all instances when the hero falls for the villain.
4 Phantom Of The Opera (2004)
Phantom of the Opera is one of the love stories that seemed doomed right from the start. The mysterious phantom, whose real name is Erik, lives in the catacombs of the Opera. He keeps his distance from people and protects his beloved Opera from people who would damage it in any way. His life changes when he falls for the young singer Christine and decides to help her career. But even though the two strike a fragile relationship and Christine is drawn to her mysterious benefactor, she falls for another man, Raoul, as well.
The movie doesn't have a happy ending, not in the traditional meaning of the word, and it's easy to feel sorry for Erik, who spends a better part of his life alone and unseen by the world. Gerard Butler is primarily known for his action roles these days but shows another side of his acting talent in the movie, and he and Emmy Rossum (Christine) work well together as a duo.
3 X-Men: The First Class (2011)
When young Raven, aka Mystique, joins the home of Charles Xavier, she falls for her adoptive brother. But Charles never sees her that way, and as years fly by, Mystique grows more and more disillusioned with hiding who she truly is. That's when the charming Erik Lehnsherr, aka Magneto, steps in and persuades her that she doesn't have to hide her real nature.
While Erik's intentions are good as he simply doesn't want his people - the Mutants - to suffer, the way he goes about achieving his goals is morally debatable. And when Mystique joins him, she goes from a hero to a villain who isn't afraid to hurt people to get what she wants.
2 Frozen (2013)
Unlike her sister Elsa who remained single, Anna eventually found love with Kristoff. The second movie involved a subplot in which Kristoff is trying to figure out a way how to propose to Anna but keeps making the situation worse. However, before these two got together, Anna fell for the seemingly charming prince Hans.
The only problem was that Hans didn't really love her and had bad intentions. Anna's naivety and her willingness to trust and marry someone she barely knew almost led to her death. Luckily, Elsa stepped in and saved her sister instead, proving that sisterly love is just as important as romantic love sometimes.
1 Star Wars: The Rise Of Skywalker (2019)
Rey and Kylo Ren spent a better part of the new Star Wars trilogy circling around each other. So naturally, the fans wondered whether anything would ever happen between them, despite the fact that Kylo Ren stood on the Dark Side. They got their answer in the third movie when Ren sacrificed himself to save Rey's life.
The two shared a sweet kiss before Kylo Ren (or Ben Solo, really) passed away. While it would have been interesting to see their romance develop now that they both were on the same side, at least Ben got his inner peace and Rey survived to tell the tale.