Enemies-to-lovers is one of the most enjoyable rom-com tropes. Watching insults double as flirting and the audience catching on before the characters is weirdly satisfying in a way that few tropes in the genre can match. This formula has raked in hundreds of millions of dollars for producers who figured out that the right mix of contempt and chemistry is a sure way to make magic happen.
The five movies on this list prove that this formula can work in any setting. It can be set in a castle, a crowded office, or even a high school hallway. It doesn’t really matter because the tension is the constant: two people trying to out-insult each other are usually the last to notice they’ve already fallen.
1. You’ve Got Mail (1998)
You’ve Got Mail sees two business rivals pour their hearts out to each other through anonymous emails. Neither knows the person on the other end is the one secretly ruining their lives during the day. Tom Hanks plays Joe Fox, the heir to a mega bookstore chain, and Meg Ryan plays Kathleen Kelly, the little children’s store owner who hates everything he and his family represent. It’s silly, it’s cozy, but the final scene where Kathleen figures it out is the whole point. That scene hit like a warm hug on a cold day.
The original idea for this movie comes from a 1940s Jimmy Stewart film called The Shop Around the Corner, which was adapted from a 1937 Hungarian play. But Nora Ephron made it feel like a fresh cup of coffee, complete with the necessary ‘90s upgrade, dial-up sounds, AOL nostalgia, and two of her favorite actors (Hanks and Ryan also starred in Ephron’s Sleepless in Seattle). The film earned over $250 million worldwide, making it Ephron’s highest-grossing movie ever.
2. 10 Things I Hate About You (1999)
This one starts with a lie. Cameron (Joseph Gordon-Levitt) wants to date Bianca (Larisa Oleynik), but he can’t because her dad has this weird rule about her older sister, Kat (Julia Stiles), dating first. One small problem, though: Kat is prickly and generally a tough nut to crack. So, to clear the path for their own romance, Cameron talks the school’s resident bad boy, Patrick Verona (Heath Ledger), into romancing Kat, with the actual bribe money coming from Bianca’s other suitor, the vain and loaded Joey Danner (Andrew Keegan). The whole thing sounds messy because it absolutely is.
But Gil Junger’s 1999 update of Shakespeare’s The Taming of the Shrew turns a paid gig into a surprisingly tender teen love story most fans still quote. Stiles plays Kat like she’s always ready for a fight, while Ledger totally nails the bad-boy bit until the paid gig starts feeling like real devotion. That scene where he sings on the bleachers? Pure chaos. And Kat’s poem at the end still brings tears to the eyes of anyone who watches it.
3. Pride and Prejudice (2005)
The most romantic thing about this movie isn’t a kiss or any of the generic speeches rom-com fans have become accustomed to. It’s a hand gesture. Darcy (Matthew Macfadyen) helps Elizabeth (Keira Knightley) into a carriage and their hands touch for maybe half a second, and he walks away flexing his hand like he just got electrocuted. That scene became the most famous part of the movie because it shows his body figuring out the depth of his feelings for Elizabeth before his brain does, exactly what director Joe Wright was going for.
He also confirmed that Macfadyen improvised the hand flex, and TikTok turned it into a viral moment years later. Before that moment, she thinks he’s too arrogant while he thinks she’s too judgemental. They’re both right, of course, but the tension that builds through all the fancy dresses and awkward dances is undeniable.
4. The Proposal (2009)
Margaret Tate (Sandra Bullock) is a terrifying book editor from Canada who’s about to get deported for visa issues. To avoid what she views as a terrible fate, she announces that she’s engaged to Andrew (Ryan Reynolds), her long-suffering assistant, who finds out about the engagement at the same time as everyone else. The panic on his face alone tells the viewer just how much they don’t get along. He plays along, but smartly negotiates himself a promotion for his troubles.
They still have to sell their love story to the immigration office and to his family, so they fly to his freezing Alaskan hometown to do just that. Betty White completely steals the show as the grandmother, just as thoroughly charmed by the fake romance as the rest of the family. They spend most of their time there needling each other, but somewhere between a male stripper and an eagle attack, real feelings sneak in.
5. The Hating Game (2021)
A corporate merger at the office is already a rough day without landing two people who can’t stand each other with facing desks. That’s Lucy Hale and Austin Stowell’s predicament as Lucy and Josh when their companies fold into one and put them close enough to hear each other’s breathing every day. With one promotion spot up for grabs, audiences watch their rivalry unfold in real time. Pretty much everything, from dress codes to who gets the corner office, becomes a game neither wants to lose.
Peter Hutchings directed this 2021 adaptation of Sally Thorne‘s best-selling novel, and Hale and Stowell play the hostility so well that when the attraction eventually catches up, it feels like a surprise attack. Critics praised their fantastic chemistry because the whole plot depended on whether viewers believed they wanted to strangle each other or kiss each other. It turns out that, with this trope, those things feel very similar.
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