The 20 Best Enemies-to-Lovers Movies, According to PureWow Editors

I'm sure you've seen this storyline before: Incredibly handsome guy meets girl. Guy and girl immediately become sworn enemies after an awkward encounter. Guy unfortunately can't avoid girl, so they bicker incessantly—but not enough to hide the sexual tension. Before you know it, guy and girl start to see each other differently and then...well, you know the rest.

Although I've seen this trope more times than I can count, there's just something so satisfying about seeing people's perceptions of each other change over time (or at least 90 minutes). One moment, they're trading eye-rolls and snarky comments and the next, they're maintaining intense eye contact, opening the door to a potential Hallmark-worthy romance. Fortunately, several movies do this quite well, thanks to compelling characters, genuine chemistry and relatable themes. From Hulu's Palm Springs to classics like You've Got Mail, here are 20 of the best enemies-to-lovers movies to add to your queue.

1. When Harry Met Sally (1989)

• Rating: R
• Genre: romantic comedy
• Director: Rob Reiner
• Cast: Billy Crystal, Meg Ryan, Carrie Fisher, Bruno Kirby

This timeless classic addresses the complications that arise when friends develop romantic feelings, and I suspect it will continue to resonate with anyone who has been there. The critically acclaimed rom-com scored an Oscar nomination for Best Original Screenplay and even spawned a stage production in 2004, starring Luke Perry and Alyson Hannigan.

PureWow Editor-in-Chief Jillian Quint says, “When Harry Met Sally might be the perfect movie period, but it is certainly the gold standard for enemies to lovers on film. When H&S meet, driving from Chicago to New York after college, they rub each other the wrong way. Then it takes years of friendship, one big fight and one iconic Katz's Deli scene to get them where they need to be.”

2. You’ve Got Mail (1998)

• Rating: PG
• Genre: Romantic Comedy
• Director: Nora Ephron
• Cast: Tom Hanks, Meg Ryan, Parker Posey, Jean Stapleton, Dave Chappelle

The nostalgic gem follows Kathleen and Joe, two competing bookstore owners who loathe each other in real life, but secretly develop romantic feelings for each other by exchanging anonymous emails online. Inspired by Miklós László's 1937 play, Parfumerie, this marked Hanks and Ryan's, third collaboration, after they worked on Joe Versus the Volcano and Sleepless in Seattle.

PureWow's VP of News and Entertainment Philip Mutz said, “Meg Ryan and Tom Hanks are the ultimate rom-com duo and this movie is the stuff that snuggling on the couch with your BF is made of. Tom Hanks is such a good 'villain' here (he makes it ok for us to root for the 'bad guy' to find love) and Meg Ryan remains unrivaled with yet another quirky, nuanced rom-com performance.”

3. Someone Like You (2001)

• Rating: PG-13
• Genre: Romantic Comedy
• Director: Tony Goldwyn
• Cast: Ashley Judd Greg Kinnear Hugh Jackman Marisa Tomei

“Someone Like You is a 2001 film that's based on a favorite chick-lit book of mine, Animal Husbandry by Laura Zigman," says PureWow Senior Editor Dana Dickey. "In the film, Ashley Judd is a TV producer who is heartbroken over her ex and ghostwrites an advice column for heartbroken women everywhere. But when she tests her psychological research on her annoyingly womanizing platonic roommate, she's surprised at what she learns. Call me a softy but the ending has me in tears every time.”

If you've ever been heartbroken, you'll totally relate to Jane as she embarks on a quest to find out why she's had such bad luck with men—and it's such a breezy, feel-good watch.

4. Me Before You (2016)

• Rating: PG-13
• Genre: Romantic Drama
• Director: Thea Sharrock
• Cast: Emilia Clarke, Sam Claflin, Janet McTeer, Charles Dance

Based on Jojo Moyes's novel of the same name, the movie tells the story of Louisa, a young woman who becomes the caregiver of a wealthy quadriplegic named Will. At first, their relationship is strained and awkward, thanks in part to Will's cynical attitude. But Louisa is determined to lift his spirits.

Beauty and Cultures Editor Chelsea Candelario says, “Me Before You is such a heart-wrenching but cute story. I don't usually get emotional watching rom-com movies, but this one surely got me, so have tissues ready. The chemistry between Emilia Clarke and Sam Claflin is so good. I know it has 54 percent on Rotten Tomatoes, but don't knock it on your rotation.”

5. Red, White and Royal Blue (2023)

• Rating: R
• Genre: Romantic Comedy
• Director: Matthew López
• Cast: Nicholas Galitzine, Taylor Zakhar Perez, Uma Thurman

The modern rom-com follows the aftermath of a minor scandal, where the son of a U.S. President and a British prince are forced to become friends to help boost the image of their respective nations. Of course, their contentious relationship eventually becomes a romantic one. And according to former PureWow Editor Joel Calfee, you'll be drawn to the "moving performances, steamy romance and a fairytale narrative that still feels novel in our current media landscape." Fans of the book, as well as those completely new to the story, will be completely enamored with Alex and Prince Henry, and when you turn off the TV, you’ll be in the mood for love"

Candelario also says, "I've watched this movie way too many times. You have a prince and the president's son hating each other before becoming so deeply in love that it'll have you squealing in your seat. It's very YA, but I love it."

6. 10 Things I Hate About You (1999)

• Rating: PG-13
• Genre: Romantic Comedy
• Director: Gil Junger
• Cast: Julia Stiles, Heath Ledger, Joseph Gordon-Levitt, Larisa Oleynik

One of my favorite tropes? Seeing the antisocial bookworm win the heart of a bad boy. In Junger's film directorial debut, a new student named Cameron devises a plan to date his crush by convincing his friend, Patrick, to date her older sister, Kat. Naturally, Patrick's efforts to win Kat over start off rocky, but he eventually breaks through, thanks in part to an epic rendition of "Can't Take My Eyes Off You." The cult classic was met with positive reviews and spawned a television reboot.

7. Pride and Prejudice (2005)

• Rating: PG
• Genre: Historical Romantic Drama
• Director: Joe Wright
• Cast: Keira Knightley, Matthew Macfadyen, Brenda Blethyn, Donald Sutherland

This charming adaptation of Jane Austen's iconic novel will give you all the feels. Both Knightley and Macfadyen nail their respective roles as enemies-turned-lovers Eliza Bennet and Mr. Darcy, and the film stays true to the book, tackling issues of social class, wealth, prejudice and morality.

According to SEO Editor Marissa Wu, "Queen Jane invented the enemies-to-lovers trope and this is why she is queen. I've read the book 20 times and watched the 2005 version five times. Kiera Knightly will always be the perfect embodiment of Eliza Bennet: Carefree, outspoken, stubborn and unafraid to play her way in a system stacked against her. And I mean...tell me what girl isn't looking for a Mr. Darcy?"

8. Something’s Gotta Give (2003)

• Rating: PG-13
• Genre: Romantic Comedy Drama
• Director: Nancy Meyers
• Cast: Jack Nicholson, Diane Keaton, Keanu Reeves, Amanda Peet 

Keaton and Nicholson join forces as two singles, Erica Barry and Harry Sanborn, who wind up living together in the Hamptons when Harry—who happens to be dating Erica's daughter—suddenly has a heart attack. As you'd expect, hilarity and awkwardness ensue, until they start to fall in love. And guys, the sizzling chemistry is everything. The rom-com grossed a whopping $266 million worldwide and earned Keaton a (well-deserved) Academy Award nomination for Best Actress.

9. The Proposal (2009)

• Rating: PG-13
• Genre: Romantic Comedy
• Director: Anne Fletcher
• Cast: Sandra Bullock, Ryan Reynolds, Malin Åkerman, Craig T. Nelson, Betty White

I will never tire of seeing Sandra Bullock and Betty White dance to "Get Low" by Lil Jon, but the chemistry between Bullock and Reynolds is a really nice bonus. The Proposal follows Margaret, a high-strung book editor who pretends to be engaged to her overworked assistant, Andrew, after learning that she's being deported to Canada. This results in plenty of bickering and hilariously awkward moments with Andrew's family. Bullock's charming performance earned her a Golden Globes nod for Best Actress in a Motion Picture Comedy or Musical.

10. Palm Springs (2020)

• Rating: R
• Genre: Romantic Comedy Drama
• Director: Max Barbakow
• Cast: Andy Samberg, Cristin Milioti, J.K. Simmons, Meredith Hagner, Camila Mendes

The Hulu flick revolves around two wedding guests who, after getting pulled into a vortex, get trapped in a time loop and fall in love as they relive the same day. The plot may sound a bit formulaic, but trust me when I say the film adds a fresh twist the the familiar storyline. The movie won a Critics' Choice Award for Best Comedy and two Golden Globe nominations for Best Motion Picture – Musical or Comedy and Best Actor in a Motion Picture – Musical or Comedy (for Samberg).

PureWow Fashion Editor Abby Hepworth says, “It's so underrated. Cristin Milioti is so talented and she and Andy Samberg have surprisingly great chemistry together. I remember when it first came out thinking it was one of the best time travel movies I've seen in a long time (all too often they're too complicated and weird) and managed to do something fun and new with a concept that's been worked over and over again. Highly recommend!”

11. The Hating Game (2021)

• Rating: R
• Genre: Romantic Comedy
• Director: Peter Hutchings
• Cast: Lucy Hale, Corbin Bernsen, Austin Stowell

Based on Sally Thorne's novel of the same name, The Hating Game follows Lucy and Josh, two rival employees who are forced to work together when their publishing companies merge. When they decided to go for the same promotion arises, their hatred for one another seems to intensify, but they can't resist their increasing physical attraction to each other, which complicates things. The effortless chemistry betwen Hale and Stowell is what really makes this movie shine.

12. 27 Dresses (2008)

• Rating: PG-13
• Genre: Romantic Comedy
• Director: Anne Fletcher
• Cast: Katherine Heigl, James Marsden, Malin Åkerman, Judy Greer

Seeing Katherine Heigl try all 27 of those bridesmaid dresses—from bright frills to prom-style gowns—just never gets old. The beloved rom-com follows Jane, a wedding enthusiast who's instantly turned off by Kevin, a reporter who has cynical views about marriage. But when he's assigned to cover her friend's wedding, the two start to bond and—you guessed it—they fall in love. Fun fact: In a shared scene between Heigl and Marsden, where Jane and Kevin are in a bar, a Josh Kelley song plays in the background. In real life, Kelley is Heigl's husband.

13. Set It Up (2018)

• Rating: TV-MA
• Genre: Romantic Comedy
• Director: Claire Scanlon
• Cast: Zoey Deutch, Glen Powell, Taye Diggs, Lucy Liu

Guys, don't sleep on this Netflix rom-com. It's laugh-out-loud funny, the cast is fantastic and it takes a fresh approach to the "enemies to friends to lovers" trope. Meet Harper and Charlie, two burnt-out assistants who plot to set up their bosses with each other, in hopes of easing their own work loads. When initial plans fall through, they realize that they have their work cut out for them. But eventually, they get more than they bargained for. FYI, Scanlon rvealed that she already had ideas for a potential sequel, so fingers crossed Netflix greenlights a part two.

14. Sweet Home Alabama (2002)

• Rating: PG-13
• Genre: Romantic Comedy Drama
• Director: Andy Tennant
• Cast: Reese Witherspoon, Josh Lucas. Patrick Dempsey

The classic film centers on Melanie, a newly engaged fashion designer who learns that her ex-husband must finalize their divorce before she can officially tie the knot. On a mission to cut ties with her ex, Jake, for good and move on, Melanie heads back home to Alabama—but things don't go according to plan. It's impossible to not be team Melanie and Jake from the get-go, even despite their initial frosty relationship. And I appreciate how thoughtfully the film explores divorce and marriage.

15. Bridget Jones’s Diary

• Rating: PG-13
• Genre: Romantic Comedy 
• Director: Sharon Maguire
• Cast: Renée Zellweger, Colin Firth, Hugh Grant, Jim Broadbent

A 32-year-old single woman keeps a special diary, where she writes about her attempts to find love. And when she least expects it, she gets entangled in a love triangle between two men. The classic rom-com, which garnered a staggering $280 million at the box office and spawned a Bridget Jones film series, earned Zellweger an Oscar nod for Best Actress.

Rachel Bowie, Senior Director of Special Projects & Royals said, “While, yes, it's flawed in many ways (the emphasis on Bridget’s weight, omg), I do adore so many elements about it — Bridget’s narration, her emergency friendship committee, heck, the sexiness that is Colin Firth. It’s silly and fun and I absolutely love Renée Zellweger as someone so charming and unselfconscious, you can't help but cheer her on!”

16. Moonstruck (1987)

• Rating: PG
• Genre: Romantic Comedy 
• Director: Norman Jewison
• Cast: Cher, Nicolas Cage, Vincent Gardenia, Olympia Dukakis

Cher stars as Loretta, an Italian-American widow who starts to fall for a man named Ronny, even though she's already engaged to his older brother. Loretta and Ronny's love-hate relationship speaks to love's complexity (and unpredictability). And thanks to the film's compelling characters and authentic portrayal of Italian-American family dynamics, it still holds up after three decades. The movie earned six Oscar nominations and won three, including the Academy Award for Best Actress (for Cher). NBD.

17. His Girl Friday (1940)

• Rating: NR
• Genre: Romantic Comedy 
• Director: Howard Hawks
• Cast: Cary Grant, Rosalind Russell, Ralph Bellamy, Gene Lockhart, Porter Hall

Walter Burns, a newspaper editor, has concocted a plan to prevent his ex-wife and investigative reporter, Hildy, from getting married to another suitor—and it seems to be working. As he distracts her with a major news story, their rivalry comes to a head, complete with zippy dialogue and banter. But their undeniable chemistry makes their dynamic all the more entertaining. The screwball comedy is an adaptation of the 1928 play, The Front Page, written by Ben Hecht Charles MacArthur.

18. Love Clinic (2015)

• Rating: PG-13
• Genre: Romantic Comedy 
• Director: Sharon Maguire
• Cast: 

The Korean film revolves around a female urologist who opens her office in the same building (and on the same floor) as a male gynecologist. Without fail, they bicker non-stop as they constantly bump into each other at work, but it's only a matter of time before their dynamic starts to shift. Yes, it gets cheesy at some points, but it's filled with humorous moments and the leads have good chemistry, which explains why it became a box-office hit in South Korea.

19. How to Lose A Guy In 10 Days (2003)

• Rating: PG
• Genre: Romantic Comedy 
• Director: Donald Petrie
• Cast: Kate Hudson Matthew McConaughey Adam Goldberg Michael Michele

Inspired by Michele Alexander and Jeannie Long's picture book of the same name, the movie follows Andie, a magazine writer who starts to date Ben, an advertising executive, as an experiment for her next story. But little does she know that Ben also has an ulterior motive. The comedic timing in this film is top notch, and I could go on about Hudson and McConaughey's solid chemistry.

Petrie told E! Online, "If you look heavily at that [first shared] scene, they are each finding out about the other at exactly the same time. And thus, they are each acting out on each other simultaneously. It's always a fun push-and-pull between these two characters that really made it so wonderful."