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Miscommunication, blindly throwing gibes, harshly misjudging each other, and ruling romance out the window the moment they meet are signs of an impending love story. These stories all have one common thread: a haze of animosity that clears up to give way to true love. The enemies-to-lovers trope is widely beloved for its witty banter, snarky comebacks, and the couple's sizzling chemistry. While exceptionally entertaining, the trope can be a serious disaster when not executed properly. While the print romances set incredibly high standards with their fake dating and fake marriage stories, those adaptations don’t always make it to the big screen. The ones who do, are littered with awkward characters, awful storylines, and forced chemistry, but there are a few best enemies-to-lovers movies that blow others out of the water.
With recent critically acclaimed romance movies, it's clear that the enemies-to-lovers trope is still as relevant and popular as ever. There's no shortage of must-see romantic movies with a narrative that fits the trope, as viewers continue to enjoy stories of characters who fall in love after a (usually) rough start.
25 'My Fair Lady' (1964)
Directed by George Cukor
Image via Warner Bros.
George Cukor's 1964 classic, My Fair Lady, is the epitome of an enemies-to-lovers film starring Audrey Hepburn and Rex Harrison. The musical rom-com follows a stuffy but intelligent professor, Henry Higgins (Harrison), who makes a bet with his colleagues that he can turn a working-class woman, Eliza Doolittle (Hepburn), into a sophisticated member of high-class society.
Hepburn and Harrison are a humorous delight in this classic film, constantly butting heads through every "lesson" and high society event, which showcases their vast differences but also their common, unspoken affection for one another. The two stars deliver exceptional performances that beautifully compliment one another and, while Harrison has no issue playing the uptight Higgins, Hepburn dazzles audiences with not just her physical but also her emotional transition.
Release Date December 25, 1964
Director George Cukor
Runtime 170 Minutes
24 'Overboard' (1987)
Directed by Garry Marshall
Image via Metro-Goldwyn-Mayer
Kurt Russell stars as a widower and carpenter, Dean Proffitt, who is hired by a wealthy but snobby woman, Joanna (Goldie Hawn), to build a shoe closet for her on her yacht, but is incredibly rude and insulting to him. When Joanna falls overboard and suffers from amnesia, her husband takes the opportunity to rid him of his insufferable wife, resulting in Dean taking his revenge out on Joanna by claiming her as his wife and the mother of his four kids.
Overboard is an underrated enemies-to-lovers romantic comedy starring real-life couple, Russell and Hawn, who are an absolute riot from start to finish. Even though the plot is a bit out there, the unwavering comedy and the movie's overall sentimental values allow audiences to overlook any potential doubt about the probability of this 80s hit. Despite negative reviews, many critics praised Hawn and Russell for their comedic chemistry, cementing Overboard as an essential enemies-to-lovers flick.
Release Date December 16, 1987
Runtime 112 Minutes
23 'When Harry Met Sally...' (1989)
Directed by Rob Reiner
Image via Columbia Pictures
When college graduates, Harry Burns (Billy Crystal) and Sally Albright (Meg Ryan) agree to drive home together from school, the road trip ensues with them arguing about whether men and women can be strictly friends. Ten years later, Harry and Sally unexpectedly cross paths again, which leads them to put their argument to the test and see if they can remain friends without things turning sexual.
When Harry Met Sally is an iconic 80s rom-com that ultimately redefined the film genre with its funny, uninhibited story and hilarious performances. Initially, the movie earned mixed reviews, some noting it to be unfulfilling and hollow, but others, including film critic, Roger Ebert, who gave the movie three out of four stars, commending Ryan and Crystal's chemistry as the film's main appeal.
When Harry Met Sally
Release Date July 21, 1989
Runtime 95 minutes
22 'A Walk to Remember' (2002)
Directed by Adam Shankman
Image via Warner Bros
In North Carolina, a popular and rebellious high school senior, Landon Carter (Shane West) makes an unexpected connection with a shy, homely girl from school, Jamie Sullivan (Mandy Moore), who used to be the target of Carter and his friend's bullying. As the two grow closer, they uncover truths about one another, forming a romance that most people are only lucky enough to read about in fairy tales.
A Walk to Remember is a bittersweet coming-of-age drama based on the 1999 novel written by Nicholas Sparks. Some would say the movie to a slightly modern take on Romeo and Juliet, but there is actual growth and understanding built between the two star-crossed lovers, giving it more depth and practicality. The film ranks as a classic mushy kind of love story with a heartbreaking twist, but despite the clichés, A Walk to Remember is still a must-see enemies-to-lovers movie that will leave a lasting impression on audiences.
A Walk to Remember
Release Date January 25, 2002
Runtime 102 Mins
21 'Two Weeks Notice' (2002)
Directed by Marc Lawrence
Image Via Warner Bros.
Sandra Bullock stars as an intelligent lawyer, Lucy, who tries to stop the Coney Island community center from being torn down by a needy billionaire, George (Hugh Grant). When George offers Lucy a job as his new Chief Counsel, she thinks the negatives outweigh the positives and believes if she accepts, she has a chance of saving the community center. As Lucy attends to George's beckoning call, she soon grows tired of his arrogance and when he agrees to hire a replacement, she starts to rethink her choice as well as her feelings for George.
Two Weeks Notice is a marginalized romantic comedy that puts a workplace spin on the traditional enemies-to-lover story structure. Grant and Bullock play off each other exceptionally well, engaging in witty banter and quick one-liners that make them the definitive couple of the rom-com genre. Even though it earned mixed reviews, today, Two Weeks Notice is celebrated as a vital enemies-to-lovers movie that takes the basic elements of the formula to new, humorous heights.
Two Weeks Notice
Release Date December 20, 2002
Runtime 101 Minutes
20 'The Hating Game' (2021)
Directed by Peter Hutchings
Image via BCDF Pictures
After their publishing companies are merged, Lucy Hutton (Lucy Hale) and Joshua Templeman (Austin Stowell) are forced to work together as executive assistants to their respective companies’ CEOs. Their stewing rivalry culminates when they’re put against each other for the same promotion. Set on achieving professional success and getting out of her lousy job, Lucy decides to go into war mode to defeat Joshua. But when an innocent elevator ride becomes heated, Lucy’s left contemplating their relationship.
Based on the Sally Thorne novel of the same name, The Hating Game is a decent book-to-film adaptation. The movie is great to watch during the holiday season, and the chemistry between the two stars ripples with possibility.
The Hating Game
Release Date December 10, 2021
Director Peter Hutchings
Runtime 102 minutes
19 'Sweet Home Alabama' (2002)
Directed by Andy Tennant
Melanie (Reese Witherspoon) is set to marry the man of her dreams, but her childhood sweetheart, Jake (Josh Lucas), is still her official husband. She resolves to make him sign the divorce papers and travels back to her hometown. Sparks fly when their long-held contempt for each other withers away, and what’s left is the love they can’t let go of.
Sweet Home Alabama is one of Witherspoon’s best movies ever, and she captures her character like a second skin. While Josh and Reese’s chemistry is already fantastic, what makes the movie stand out is that they’re already married and rekindling the love they thought they’d lost.
Sweet Home Alabama
Release Date September 27, 2002
Director Andy Tennant
Cast Patrick Dempsey, Candice Bergen, Reese Witherspoon, Melanie Lynskey, Josh Lucas, Fred Ward
Rating PG-13
Genres Romance, Comedy
18 'Red, White & Royal Blue' (2023)
Directed by Matthew López
Image Via Prime Video
Based on the novel of the same name by Casey McQuiston, Matthew López's movie illustrates a feud between the son of the American President and Britain's prince, which threatens to drive a wedge in U.S./British relations. Naturally, they are then forced into a staged truce.
Like other films in the category, Red, White & Royal Blue sees its protagonists facing forced proximity, with their real feelings developing over time. Despite the initial tension between the two characters, Alex and Henry share their fears and vulnerabilities, giving way to a deeper connection that grows as their own self-development journey takes place. While not an astounding feature, Red, White & Royal Blue is a decent LGBTQ+ watch elevated by Nicholas Galitzine and Taylor Perez's chemistry. – Daniela Gama
Release Date August 11, 2023
Director Matthew Lopez
Runtime 121 Minutes
17 'Anyone But You' (2023)
Directed by Will Gluck
Image via Sony Pictures Releasing
Sydney Sweeney and Glen Powell join forces in this 2023 romantic comedy that follows ex-lovers Bea and Ben as they reconnect at a destination wedding in Australia. To avoid awkwardness and to earn (or lose) the attention of their ex-partners, they pretend to be a couple with funny results. Needless to say, their fake relationship gradually develops.
While Anyone But You is a great fit for those who enjoy both the fake dating and the enemies-to-lovers tropes, as the relationship between the central characters fits between the two. It may not be a groundbreaking picture in the rom-com genre, however, this loose adaptation of William Shakespeare's Much Ado About Nothing illustrates an intense love story with just enough bickering and chemistry to keep viewers engaged. – Daniela Gama
Release Date December 22, 2023
16 'In Time' (2011)
Directed by Andrew Niccol
Set in 2169, In Time's dystopian version of the world has the technological capability to stop human aging at 25, which is when their timer (on their forearm) begins. Those from lower-income zones have to work hard to get additional hours to live, while those from the richest areas are essentially immortal. When 28-year-old Dayton (Justin Timberlake) manages to cross zones on stolen time, things go horribly wrong and he abducts 27-year-old Sylvia (Amanda Seyfried), the daughter of a wealthy businessman.
The fact that he kidnaps her tells audiences much of what they need to know about the beginning of their relationship. Sylvia finds herself in the poorest zone, which shocks and changes her perspective. This sci-fi movie that was ahead of its time has an interesting take on the trope that is woven together with commentary on class structure and inequality.
Release Date October 20, 2011
Director Andrew Niccol
Runtime 109minutes
15 'The Cutting Edge' (1992)
Directed by Paul Michael Glaser
Image via MGM
This must-see sports romance by Paul Michael Glaser sees a temperamental, highly disciplined figure skater (Moira Kelly) and an arrogant yet laid-back former hockey player (D.B. Sweeney) team up to win the Olympic Gold Medal as a figure skating team.
Featuring tons of banter and chemistry, The Cutting Edge is also a must-watch in the niche enemies-to-lovers category. Even though Kate and Doug's conflicting personalities and forced proximity make it difficult for them to get the medal, the two characters gradually connect and are brought together through shared experiences. Over time, they eventually showcase their initial strong attraction and a deep romance story naturally develops. – Daniela Gama
Release Date March 27, 1992
Director Paul Michael Glaser
Runtime 101 Minutes
14 'The Proposal' (2009)
Directed by Anne Fletcher
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Image via Walt Disney Studios Motion Pictures
Andrew Paxton (Ryan Reynolds) hates his boss Margaret Tate (Sandra Bullock), because of how terribly she treats her employees, especially Andrew himself. When Margaret learns her visa is about to expire soon, and she’ll have to return to Canada if she doesn’t figure out a solution, she convinces Andrew to marry her. They travel to Alaska to meet his family and get married, but shocking realizations stark them, leading to the obvious (yet awaited) happy ever after.
The comedy is spot-on and makes viewers want to roll into blankets and stay there watching forever. While Sandra Bullock’s best films hold their record for being exceedingly hilarious and wholesome, The Proposal is one of the most incredibly written and performed films ever.
The Proposal
Release Date June 19, 2009
Runtime 108 Minutes
13 'Palm Springs' (2020)
Directed by Max Barbakow
Image via Hulu
Palm Springs is one of the most unique haters-to-lovers movies and an entertaining rom-com with a sci-fi twist. It's centered on Nyles (Andy Samberg) and Sarah (Cristin Milioti), who meet at a wedding and have some fun. When a bizarre incident leads Sarah toward a vortex that Nyles walks into, she wakes up stuck in a time loop with him.
The conflict between them comes from Nyles' nihilistic outlook about the strange situation they're in, which frustrates Sarah, who wants to escape the endless loop of the day of her friend's wedding. More shocking revelations only make the rift worse, even though it's clear that they could be a great couple. It's a goofy movie that manages to make viewers feel invested in the protagonists' love story.
Release Date July 10, 2020
Director Max Barbakow
Runtime 90 minutes
12 'Avatar' (2009)
Directed by James Cameron
Image via 20th Century Studios
Avatar became a cultural phenomenon when it was first released, as it introduced the fantastical world of Pandora. Humans are attempting to colonize and mine the habitable moon, while also planning to deal with its Na'vi inhabitants in questionable ways. Among those sent to the moon (on promises of wealth and advanced healthcare) is Jake Sully (Sam Worthington). While initially determined to fight the war, his encounter with Neytiri (Zoe Saldana) changes his life.
The enemies-to-lovers trope in this case is set against a grand backdrop of warfare, community, and trust. Jake goes through a transformation throughout the film that helps him realize the greed and corruption that drives humans – it's something he wouldn't have been able to see without the originally hesitant Neytiri. The incredibly successful continuation of their love story, Avatar: The Way of Water, further explored their relationship and its impact on the ongoing struggle for their home.
Release Date December 15, 2009
Director James Cameron
Runtime 162 minutes
11 'Moonstruck' (1987)
Directed by Norman Jewison
Loretta Castorini (Cher) is engaged to Ronny’s brother, but she feels they don’t have any connection or sparks. Her mother, however, finds this appropriate and tells her it’s a good thing because when you marry someone you love, “they drive you crazy.” Things go berserk when Loretta realizes that it is, in fact, Ronny (Nicolas Cage) who drives her wild.
Despite their love-hate relationship, they have undeniable chemistry. By the end of Moonstruck, they resolve things and prove that love can be wild, stupid, yet beautiful. The movie was one of Nicolas Cage's best works, and its accolades stand for it. Albeit unconventional, the love story makes you swoon for itself.
Release Date December 16, 1987
Director Norman Jewison
Runtime 102 minutes
10 'Clueless' (1995)
Directed by Amy Heckerling
Cher Horowitz (Alicia Silverstone) and her ex-stepbrother Josh Lucas (Paul Rudd) are sworn nemeses. He thinks she’s “a superficial space cadet,” and she believes he’s a brown-nosing freeloader who should go “torture another family.” They aren’t too cutthroat but have a massive sibling rivalry without any room for support. As the movie progresses, it becomes evident to everyone how “clueless” they are. But when Josh stands up for Cher, they give in to their feelings to give their whirlwind romance a chance.
While romance takes a backseat to Cher’s decision for the iconic makeover, the chemistry ripples throughout the movie, leading to a sweet ending. Not surprisingly, Clueless was a high point in Rudd's career and one of the best movies in Silverstone’s.
Release Date July 19, 1995
Director Amy Heckerling
Runtime 97 minutes
9 'You've Got Mail' (1998)
Directed by Nora Ephron
Image via Warner Bros.
Kathleen Kelly (Meg Ryan) is the owner of a small and special bookshop. When Joe Fox (Tom Hanks) opens a mega book emporium around the corner, she’s almost run out of business. Their feud continues until one day, Joe realizes that Kathleen is his online best friend, the confidant he’s been trusting all along. The realization helps him see her in a fresher light, and eventually, he wins her over.
A classic case of the two-person love triangle, You've Got Mail is one of the best movies of the enemies-to-lovers trope. It's a heartwarming, and at times poignant reminder that love is a powerful thing.
Release Date December 18, 1998
Director Nora Ephron
Runtime 119 minutes
8 'Dirty Dancing' (1987)
Directed by Emile Ardolino
Johnny Castle (Patrick Swayze) and Frances "Baby" Houseman (Jennifer Grey) make up a couple that is a one-of-a-kind example of a great enemies-to-lovers dynamic. While Baby is the daughter of a wealthy daddy and has a princess lifestyle, Johnny is an employee famous for his smooth moves and tends to hang with the tougher crowd. They hate each other at first sight, but their relationship deteriorates further when they’re forced to train together for a dance competition. Over time, as they truly get to know each other, they realize they have a deeper connection that roots deeper than their smooth moves.
The movie is a classic, and even those who haven’t watched Dirty Dancing will know its iconic behind-the-scenes facts. A sequel starring Jennifer is under development at Lionsgate, and while the great-late Patrick Swayze isn’t on the cast, he will be deeply missed.
Release Date August 21, 1987
Director Emile Ardolino
Cast Jennifer Grey , Patrick swayze , Jerry Orbach , Cynthia Rhodes , Jack Weston , Jane Brucker
Runtime 100 minutes
7 'How to Lose a Guy in 10 Days' (2003)
Directed by Donald Petrie
When How to Lose a Guy in 10 Days begins, Andy Anderson (Kate Hudson) and Benjamin Berry (Matthew McConaughey) consider each other nothing more than attractive targets for the next steps in their respective careers. She is tasked with making him “wish he was dead,” and he has to make her fall in love with him
All their efforts go down the tubes when true love takes over the driving wheel. When the truth comes out, hatred replaces heartbreak. They lose each other towards the end, but just long enough to know they never want to lose each other again. With the couple trying to deceive each other, the movie is a fun ride, and the chemistry between Hudson and McConaughey is excellent.
How to Lose A Guy In 10 Days
Release Date February 7, 2003
Director Donald Petrie
Runtime 116 minutes
6 'Silver Linings Playbook' (2012)
Directed by David O. Russell
Image via The Weinstein Company
In Silver Linings Playbook, Pat Solitano Jr. (Bradley Cooper) is struggling to piece his life back together after losing his house, job, and, most importantly, his ex-wife. He lives with bipolar and has recently been released from a mental health facility, and soon encounters Tiffany Maxwell (Jennifer Lawrence). Pat decides that it's best to avoid Tiffany, who is mysterious and erratic, while he recovers and tries to convince his ex that they can be together again.
Pat is initially annoyed by Tiffany's advances and considers her dangerous, but is soon persuaded to strike a deal with her that could help him impress his ex. Their love story is told in a humorous, thoughtful, and often frantic way that captures how messy but necessary their relationship is (for both of them).
Release Date November 16, 2012
Director David O. Russell
Runtime 122 Minutes
English (US) ·