Romance has many tropes, from fake dating to forbidden love, but few storylines deliver as much irresistible tension as the enemies-to-lovers trope. Whether it’s clashing egos, rival shop owners, or intellectual adversaries, watching two people go from trading insults to falling hopelessly in love never loses its charm. These stories of pride melting into affection serve as reminders that love can be found in the most unexpected places. They teach us not to judge a book by its cover, and the importance of letting our guard down.
From irresistible ’90s romcoms to modern streaming hits, these movies capture the spark that ignites when opposites collide, making viewers swoon and believe in magic. The best ones balance friction and feeling, and sometimes humor and emotion. The 10 romantic films depict some of the best tales where enemies turn to lovers.
‘You’ve Got Mail’ (1998)
Inspired by Miklóz Láslóz’s 1937 play Parfumerie, You’ve Got Mail marks Meg Ryan and Thomas Hanks’ third collaboration. When Joe Fox, owner of Fox Books, opens a mega book emporium around the corner, Kathleen Kelly’s small indie bookshop finds itself threatened. A feud ensues between the business enemies, but unbeknownst to them, they’ve already been getting to know each other through an anonymous chatroom. Their witty exchange evolves into emotional intimacy, and the two fall in love before connecting the dots.
A Quintessential ’90s Romance
You’ve Got Mail captures the beauty of developing feelings for someone and the power that love can have. The magic of this Nora Ephron film lies in its blend of old-fashioned romance and the dawn of the digital age. As Kathleen and Joe’s professional rivalry gives way to affection, the film explores vulnerability, forgiveness, and how love can blossom in the most unexpected of ways. Despite its ’90s setting, this classic enemies-to-lovers tale feels timeless.
’10 Things I Hate About You’ (1999)
This reimagining of William Shakespeare’s The Taming of the Shrew follows the fiercely independent Kat (Julia Stiles) and her younger popular sister, Bianca (Larisa Oleynik). When their overprotective father decides Bianca can only date once Kat does, Patrick (Heath Ledger), the bad boy of Padua High School, is paid to date Kat by two of Bianca’s suitors. Initially, she wants nothing to do with him and their relationship is contentious, but eventually real feelings arise on both sides.
An Iconic Work
10 Things I Hate About You captures the sizzling tension between two strong-willed personalities who challenge each other, teach each other to grow, and make one another want to open up. By the end, their journey from adversaries to lovers feels authentic. The chemistry between Ledger and Stiles crackles with intensity, with both actors stealing the show. To this day, the movie remains one of the best coming-of-age romances of all time.
‘How to Lose a Guy in 10 Days’ (2003)
Kate Hudson stars as Andie Anderson, a journalist who works at the women’s magazine Composure, and who is determined to write a hit article on how to drive a man away. Meanwhile, Matthew McConaughey’s Ben Barry, a confident advertising executive, bets that he can make any woman fall madly in love with him to win a coveted account. What ensues is mutual deception and a hilarious duel of manipulation. As they both go up against a 10-day deadline, an unexpected meeting of the hearts takes place.
One of the Best Romcoms of All Time
How to Lose a Guy in 10 Days is a highly entertaining and surprisingly heartfelt enemies-to-lovers romcom. What starts as playful sabotage transforms into genuine connection as each protagonist drops their facade. The film thrives on the magnetic energy between both leads, balancing hilarious moments with flashes of real emotion. Beneath the comedy is a story that teaches that in romance, authenticity will always win out over games.
‘Pride and Prejudice’ (2005)
Directed by Joe Wright with a screenplay by Deborah Moggach, the 2005 adaptation of Jane Austen’s classic novel remains a gold standard for enemies-to-lovers storytelling. The epic love story follows Elizabeth Bennett (Keira Knightley) and Mr. Darcy (Matthew Macfadyen), who clash from their very first meeting, becoming intellectual adversaries — both too proud, too stubborn, and too quick to judge. Yet beneath their tense exchanges, lies an undeniable attraction.
From Enemies to Soulmates
This rendition of Pride and Prejudice captures the vulnerability beneath both characters’ guarded exteriors. The breathtaking cinematography and charged silences amplify the tension between them, with every frame brimming with longing. As they both soften, their journey becomes one of humility and understanding. From the iconic, rain-soaked confrontation to the tender second proposal at dawn, everything about this movie feels both epic and intimate.
‘The Proposal’ (2009)
Sandra Bullock stars as Margaret Tate, the fearsome and demanding editor-in-chief at a New York book publishing company. When she faces deportation back to Canada, she forces her assistant Andrew Paxton (Ryan Reynolds) into a fake marriage to avoid leaving the country and her job. Their mutual disdain is palpable, but as they travel to Andrew’s Alaskan hometown to make their relationship seem genuine, the lines between pretense and passion begin to blur.
A Hilarious and Tender Love Story
The Proposal is equal parts hilarious and heartwarming, beautifully balancing big comedy and deadpan humor with heartfelt emotion. Beneath the laughter lies a sincere exploration of vulnerability and self-awareness. As Margaret begins to spend more and more time with Andrew’s loving family, the ice queen’s guard begins to melt, and Andrew begins to see a softer side of her. If you enjoy a tale about opposites attracting, this enemies-to-lovers story will appeal to you.
‘Set It Up’ (2018)
Set It Up is a bit different from the other entries on this list in that the enemies-to-lovers tale involves the central characters going from adversaries to friends, and then from friends to lovers. Glen Powell and Zoey Deutch star as Charlie and Harper, two overworked assistants working in the same building. In an attempt to give themselves a break and find some peace, the two strike up the idea of setting their demanding bosses up together, only it ends up in disaster.
An Irresistible Romcom
As they scheme together, their initial snarky teamwork turns into camaraderie. From deep friendship, love is born, and they discover that what they were truly looking for was more meaning. As is the case in the greatest romantic films, what makes this picture thrive is the chemistry between its two leads. Deutch and Powell are incredibly convincing. Set It Up is a great movie to watch when you’re craving a romance that builds slowly. From cheesy bits to poignant musings, the movie has everything you could want in a romcom.
‘Palm Springs’ (2020)
Palm Springs brings something fresh to the genre by taking the enemies-to-lovers trope and tossing it into a time-loop story. Nyles (Andy Samberg) and Sarah (Cristin Milioti) meet each other at a wedding and have some fun. After a bizarre incident, Sarah follows Nyles into a cave, only to be sucked into a time vortex. The two are cursed to relive the wedding day over and over again — and cannot stand each other, at first. As they find themselves exhausting all possibilities to escape, they develop deep feelings for one another.
A Movie of Existential Dread and Romance
In this sci-fi set-up, absurdist comedy and raw emotion blend together to explore self-growth, the importance of real connection, and finding meaning in a meaningless world. The movie adds layers of nuance to typical romcom conventions, creating something that is both achingly hilarious and incredibly touching. Ultimately, Palm Springs teaches viewers that sometimes the key to breaking free is finding love and someone who challenges you.
‘Rosaline’ (2022)
Rosaline is based on the 2012 novel When You Were Mine by Rebecca Serle, which is inspired by Shakespeare’s Romeo and Juliet. In the original tale, Rosaline rejects Romeo’s advances. But in this medieval-set story, Rosaline (Kaitlyn Dever) is very much in love with Romeo (Kyle Allen), who dumps her for her younger cousin, Juliet (Isabel Merced). Determined to sabotage their relationship, Rosaline schemes with her arranged suitor Dario (Sean Teale), who she has an antagonistic dynamic with.
A Charming Romcom With Classic Roots
As all enemies-to-lovers stories go, Rosaline begins to soften towards Dario and realizes that someone like him is who she has always wanted. Through humor and modern sensibility, the film reclaims a sidelined character in a celebration of self-growth and unexpected love. Rosaline proves that heartbreak can always lead to new, truer love.
‘Red, White & Royal Blue’ (2023)
Based on the bestselling novel by Casey McQuiston, Red, White & Royal Blue is one of the best queer romcoms to have come out in recent years. The story focuses on Alex Claremont-Diaz (Taylor Zakhar Perez), the son of the American President, and Britain’s Prince Henry (Nicholas Galitzine). After getting into a fight at a wedding, the two are forced to go on appearances and pretend to be friends to save face. Soon, rivalry and forced friendship blossom into something more.
A Lighthearted, Engaging Movie
The movie blends sharp political satire with heartfelt romance. It’s absolutely swoon-worthy to see Alex and Henry’s relationship turn from defiant to tender. With a witty dialogue, palpable chemistry, and globe-trotting to spare, Red, White, & Royal Blue is a modern standout that defies tradition.
‘Anyone but You’ (2023)
This movie is very loosely adapted from Shakespeare’s Much Ado About Nothing. After a horrible first date, Bea (Sydney Sweeney) and Ben (Glen Powell) are surprised to run into each other over an intimate wedding getaway vacation. In order to get her parents off her back about law school and her ex-boyfriend, and to make Ben’s ex-girlfriend think he’s over her, the two pretend to date, despite despising one another. Soon, the pretense gives way to real love.
A Romantic Hit
Anyone But You proves that romcoms aren’t dead. Not only did the movie revive the genre, but it made over $216.3 million on a $25 million budget. Sweeney and Powell’s scorching chemistry is palpable. Their banter is witty, their back-and-forth is electric, and every insult is charged with sexual tension. Beneath all the snark, lies a tale about two people discovering love, vulnerability, and trust.
This story originally appeared on Movieweb
