The 12 Best Enemies-To-Lovers Movies Ever, Ranked

It’s no surprise that the “enemies-to-lovers” storyline is a significant element in popular culture. On television, you’ll find pairs like Chuck Bass and Blair Waldorf (played by Ed Westwick and Leighton Meester) from “Gossip Girl,” Buffy and Spike (portrayed by Sarah Michelle Gellar and James Marsters) from “Buffy the Vampire Slayer,” and let’s not forget Sam Malone and Diane Chambers (Ted Danson and Shelley Long) on “Cheers.” As for its presence in films, examples include The Beast and Belle (Dan Stevens and Emma Watson) in “Beauty and the Beast” and Jackman and Wolverine (Hugh Jackman and Patrick Stewart) from the X-Men series.

Many films showcase the enemies-to-lovers storyline, but which ones truly stand out? While it’s important to mention that each of these movies handles this trope exceptionally well, this ranking isn’t meant to be a traditional “worst to best” list. Instead, think of it as a journey from “pretty great” to “absolutely brilliant.” Below you will find twelve extraordinary, captivating, and heartwarming enemies-to-lovers movies… in order! (As an added perk, many of these films have running times under two hours, so feel free to watch several back-to-back if you’re up for a marathon session!)

12. The Proposal

In many romantic stories, characters who initially dislike each other end up falling in love (the enemies-to-lovers trope). Frequently, this is combined with a situation where they pretend to be a couple for some plot reason, which is exactly what happens in the 2009 comedy “The Proposal.” When Margaret Tate, a high-powered publishing executive (played by Sandra Bullock), learns she might be deported from New York due to a visa problem, she convinces her overworked assistant Andrew Paxton (Ryan Reynolds) to marry her so she can get a green card. In return, she promises him a promotion.

In the course of their scheme, Andrew takes Margaret to the quaint Alaskan town of Sitka, introducing her to his family: Joe, a stern father (portrayed by Craig T. Nelson), Grace and Annie, his loving mother and grandmother respectively (played by Mary Steenburgen and Betty White). It becomes evident that real emotions between Margaret and Andrew blossom during their stay in Alaska, especially as Andrew discovers the gentler, compassionate side of his usually overbearing superior. The pair share an outstanding chemistry, and a humorous performance from the late Betty White contributes to this film’s place among the top enemies-to-lovers stories.

Lead Actors: Ryan Reynolds, Sandra Bullock, Betty White
Directed By: Anne Fletcher
Rating: Rated PG-13
Running Time: 1 hour and 48 minutes
Available For Purchase or Rental

Starring Ryan Reynolds, Sandra Bullock, and Betty White. Directed by Anne Fletcher. It’s rated PG-13 and runs for 108 minutes. You can buy or rent it to watch.

11. Set It Up

Discussing the characters of Harper Moore and Charlie Young from “Set It Up” (2018), portrayed by Zoey Deutch and Glen Powell, we find them both battling to satisfy their tough bosses – Kirsten Stevens, a renowned sports journalist (Lucy Liu), and Rick Otis, a venture capitalist (Taye Diggs). In a serendipitous encounter while collecting dinner orders, Harper and Charlie, who have a mutual dislike for each other, come up with a plan: why not let their bosses go on a date? Could it be that they would loosen up at work just a bit?

Kirsten and Rick quickly formed a good connection, reducing the work burden for Harper and Charlie. However, they had to intervene when Rick and Kirsten prioritized their jobs over their relationship. As time went on, Harper and Charlie grew closer due to sharing similar professional aspirations; Charlie desired a higher role at Rick’s firm, while Harper dreamed of becoming a sports journalist instead of continuing as Kirsten’s assistant. When Charlie’s girlfriend became distant because of his demanding job, tensions ignited between him and Harper. “Set It Up” is a delightful movie, one of Netflix’s top original romantic comedies, showcasing that Deutsch and Powell are exceptional actors.

Movie Details:
– Starring: Glen Powell, Zoey Deutch, Taye Diggs, Lucy Liu
– Director: Claire Scanlon
– Rating: R (Mature Audience)
– Duration: 105 minutes
– Platform: Netflix

In this film, you’ll find Glen Powell, Zoey Deutch, Taye Diggs, and Lucy Liu in the cast. The director of this movie is Claire Scanlon. It carries an R rating and lasts for 105 minutes. You can catch it on Netflix.

10. 10 Things I Hate About You

10 Things I Hate About You, a hilarious teen comedy reminiscent of Shakespeare’s “The Taming of the Shrew,” casts me as Kat Stratford, a sharp-tongued senior at Padua High School. My dad, Walter Stratford (played brilliantly by Larry Miller), has this crazy rule: my younger sister Bianca can’t date until I do. Since I despise the idea of dating, my sister’s admirer Joey Donner hires a mysterious guy named Patrick Verona (Heath Ledger) to win me over, so he can ask Bianca out. But

In “10 Things I Hate About You,” the extraordinary chemistry between Stiles and Ledger, coupled with a witty, side-splitting script by Karen McCullah and Kirsten Smith, transforms this teen movie into more than just a classic coming-of-age story. It offers a fresh, contemporary twist on the time-honored tale of adversaries becoming lovers.

Lead Actors: Heath Ledger, Julia Stiles, Joseph Gordon-Levitt
Director: Gil Junger
Rating: Rated PG-13
Duration: 97 minutes
Streaming Platform: Disney+ (where you can watch it)

9. Dirty Dancing

It’s more than just obvious that Johnny Castle, portrayed by Patrick Swayze in the 1987 film “Dirty Dancing”, initially holds little regard for the green and inexperienced vacationer Frances “Baby” Houseman (played by Jennifer Grey). To put it mildly, their initial encounter doesn’t exactly spark a warm friendship. Intriguingly, it’s said that tension between Swayze and Grey also existed off-screen during filming. As the Housemans spend their summer at a Catskills resort, Johnny serves as a dance instructor and performer, and when his regular partner Penny Johnson (Cynthia Rhodes) is unable to dance with him, threatening his season’s earnings, Baby steps in to train as his new partner.

Dirty Dancing” isn’t just a moving depiction of Baby’s personal journey during her summer, but it was also incredibly forward-thinking for its era. The character Penny, who faces complications after an unsafe abortion, is saved by the intervention of Baby’s father, played by Jerry Orbach, who is a doctor. As the movie reaches its climax, with Baby dancing exuberantly in Johnny’s arms as “(I’ve Had) The Time of My Life” plays, you’ll find yourself cheering for the unconventional pair, Baby and Johnny, to triumph against all odds.

Starring: Patrick Swayze, Jennifer Grey, Jerry Orbach
Directed by: Emile Ardolino
Rating: Suitable for ages 13 and up
Running time: 1 hour and 40 minutes
Where to enjoy: Available for purchase or rental

Stars: Patrick Swayze, Jennifer Grey, Jerry Orbach
Directed by: Emile Ardolino
Rating: PG-13
Duration: 100 minutes
Watch: Can be purchased or rented

8. Palm Springs

2020’s summer was a dismal period for most, yet we managed to produce an exceptional enemies-to-lovers romantic comedy as a result – “Palm Springs.” Released on Hulu following a fierce bidding war at Sundance in January, this movie marked Max Barbakow’s directorial debut and starred Andy Samberg and Cristin Milioti. They both delivered captivating performances in this delightful time-loop comedy.

In Palm Springs, Sarah (Milioti) journeys to a resort for her half-sister’s wedding, where she encounters an unusual man named Nyles (Samberg), who seems familiar with her and persuades her to abandon the reception for a nighttime adventure in the desert. However, upon waking up the next day, Sarah discovers that the date, November 9, is mysteriously repeating itself. It’s eventually revealed that Nyles has been stuck in this time loop for quite some time. At first, Sarah resists accepting her peculiar predicament, but eventually recognizes she must rely on and trust Nyles if they are to escape the loop. “Palm Springs” is a humorous, emotionally resonant film with standout performances from Milioti, Samberg, and J.K. Simmons, making it well worth watching. Additionally, the Lonely Island team set a new Sundance sales record by 69 cents, which adds to their impressive legacy.

Actor Lineup: Andy Samberg, Cristin Milioti, J.K. Simmons

Behind the Camera: Max Barbakow

Rated: R (Restricted)

Duration: 90 minutes

Stream it on: Hulu

7. Red, White & Royal Blue

In the novel “Red, White & Royal Blue” by Casey McQuiston, published in 2023, we imagine a scenario where the First Son of the United States, Alex-Claremont Diaz, and Prince Henry of England find themselves falling in love. The story begins when Alex travels to London for a royal wedding, but an unexpected altercation between him and Prince Henry causes an international incident. To smooth things over, they pretend to be close friends, which eventually leads them towards genuine affection.

Red, White & Royal Blue” beautifully showcases Alex’s journey of self-acceptance as he embraces his bisexuality, combined with the charming romantic chemistry between Zakhar-Perez and Galitzine, makes it a genuinely delightful romantic fantasy. However, Uma Thurman’s strong Texan accent as a president can be somewhat noticeable. Despite this minor distraction, it’s wonderful that this film offers valuable representation for the limited number of quality queer rom-coms currently available.

Actor Lineup: Taylor Zakhar-Perez, Nicholas Galitzine, Uma Thurman

Director: Matthew López

Rating Information: Rated R

Run Time: 1 hour 58 minutes

Streaming Platform: Amazon Prime Video

6. The Sound of Music

In Robert Wise’s 1965 movie musical “The Sound of Music,” you might not initially associate the enemies-to-lovers trope due to Captain Georg von Trapp (played by Christopher Plummer) and his unconventional governess Maria (portrayed by Julie Andrews). At their first encounter, Captain von Trapp is far from thrilled with Maria’s spontaneous remarks and carefree spirit. Maria, who was dismissed (in essence) from an Austrian convent for her repeated defiance of the nuns’ rules, eventually forms a connection with the Captain’s seven children. Over time, he comes to appreciate Maria’s appealing nature.

It’s worth mentioning that “The Sound of Music” starts off with a playful, carefree narrative, eventually leading to a dramatic third act where the Captain and Maria (now married) have to flee Austria to avoid Nazi authorities. Despite its unconventional twist on the enemies-to-lovers genre, it remains one of the greatest movie musicals ever produced, with Julie Andrews and Christopher Plummer delivering outstanding performances in their romantic roles.

Starring: Julie Andrews, Christopher Plummer
Director: Robert Wise
Rating: Suitable for All Ages (G)
Duration: 2 hours and 54 minutes
Watch it on: Disney+

5. Singin’ in the Rain

Singin’ in the Rain” isn’t just one of the greatest movie musicals ever produced; it might even be the best in its category. But what makes it stand out is that it’s also a cleverly disguised enemies-to-lovers story! In this tale set during the golden age of silent films, stars Don Lockwood (played by Gene Kelly) and Lina Lamont (Jean Hagen) dominate Hollywood. However, the arrival of the real movie “The Jazz Singer” transforms the entire industry into one that relies on “talkies.” The challenge for Don and Lina is that Lina can’t sing, and her voice is quite harsh – a fact that Jean Hagen hilariously portrays in her performance.

As I, a passionate gamer, step into the shoes of Kathy Selden, an aspiring actress with a golden voice, I find myself taking over Lina’s part in the fresh musical film, “The Dancing Cavalier.” At first, Kathy and Don don’t see eye to eye – she criticizes the silver screen and he bristles at her words. However, as the story unfolds, our friendship blossoms into a beautiful romance, with Don becoming my staunch advocate for the remarkable work I do. “Singin’ in the Rain,” released way back in 1952, remains a charming classic even today, and its captivating tale of adversaries turned lovers is simply unforgettable.

Cast: Gene Kelly, Donald O’Connor, Debbie Reynolds, Jean Hagen
Directors: Gene Kelly and Stanley Donen
Rating: General Audiences (G)
Duration: 103 minutes
Streaming on: HBO Max

4. Clueless

Setting aside the debates about the taboo nature of their relationship, I must admit that “Clueless” is an exceptional enemies-to-lovers movie, reminiscent of Jane Austen’s “Emma”. When we are introduced to Cher Horowitz, portrayed brilliantly by Alicia Silverstone, she’s the queen bee of her California high school, ruling alongside her best friend Dionne Davenport (Stacey Dash). However, it’s not a reign with an iron fist; instead, she takes in a new student, Tai Frasier (Brittany Murphy), into her circle.

As the movie unfolds, we witness Cher’s interactions with her stepbrother Josh, played by Paul Rudd. Although their father, Mel Horowitz (Dan Hedaya), and Josh’s mother had a brief relationship, he still cares for Josh, a college student. Yet, it isn’t until Cher experiences a failed romance with a high school peer named Christian Stovitz (Justin Walker) that she comes to the realization that her ideal man has been by her side all along.

Once more, the discussion about Cher and Josh as a couple seems rather pointless, but truth be told, they complement each other wonderfully. Cher balances out Josh’s seriousness, while he encourages her to consider others beyond herself. Amy Heckerling’s adaptation of “Emma” is both amusing and heartfelt, and indeed, their relationship is perfectly acceptable.

Actor Lineup: Alicia Silverstone, Paul Rudd, Dan Hedaya

Director: Amy Heckerling

Rating: Suitable for ages 13 and up

Duration: 97 minutes

Streaming Platform: Paramount+

Starring: Alicia Silverstone, Paul Rudd, Dan Hedaya

Directed by: Amy Heckerling

Rated: For viewers aged 13 and above

Length: 97 minutes

Where to watch: Paramount+

3. Pride & Prejudice (2005)

Director Joe Wright is well-versed in lavish, romantic period dramas, as evidenced by films like “Atonement” and “Anna Karenina.” His 2005 adaptation of Jane Austen’s “Pride & Prejudice” is widely regarded as one of the finest screen adaptations of the classic enemies-to-lovers tale. The Bennet family boasts several eligible bachelorettes, with Elizabeth (portrayed by Keira Knightley) being one of them, but she’s largely indifferent towards the notion of marriage. Encountering the aloof wealthy bachelor Mr. Darcy (Matthew Macfadyen) doesn’t pique her interest in matrimony either. As Darcy’s adversary George Wickham (Rupert Friend) woos Elizabeth’s sister Jane (Rosamund Pike), they spend more time together. If you don’t find yourself smitten when Darcy eventually declares his love for Elizabeth, it might indicate a lack of emotional responsiveness (to put it mildly), and let’s not forget about Darcy’s iconic hand gesture on the Internet!

The chemistry between Knightley and Macfadyen is captivating; it’s nearly unimaginable that the latter would transform into the sly Tom Wambsgans on “Succession” later in time. Despite its familiarity, Wright’s adaptation underscores the importance of retelling this story. Enemies-turned-lovers narratives seldom surpass this one in quality.

Starring: Keira Knightley, Matthew Macfadyen, Rosamund Pike, and Donald Sutherland, this film is directed by Joe Wright. It’s rated PG and runs for 127 minutes. You can catch it streaming on Netflix.

2. Bridget Jones’s Diary

Remarkably, Sharon Maguire’s 2001 romantic comedy “Bridget Jones’s Diary” and Helen Fielding’s novel of the same name share similarities with Jane Austen’s classic “Pride & Prejudice.” Renee Zellweger delivers a stellar performance as Bridget Jones, a character who is remarkably relatable and less prickly than Elizabeth Bennett. The film version even earned her an Oscar nomination. In the story, Bridget juggles her quest to drink less, lose weight, and find love in London while working for a publishing company, but her boss, Daniel Cleaver (played by Hugh Grant), often thwarts these plans with his antics. On New Year’s Day at her mother’s annual “turkey curry buffet,” Bridget meets Mark Darcy (Colin Firth) and neither of them are immediately smitten, but as Bridget continues to see Daniel, Mark steps in to warn her about him. In the course of their interaction, he expresses his fondness for Bridget just as she is, which becomes one of the most heartwarming romantic scenes in the history of rom-coms.

To date, Bridget Jones, played by Renée Zellweger, has appeared in three sequels, but the original “Bridget Jones’s Diary” stands out as the finest. In this film, Grant and Firth engage in a delightful rivalry as they both vie for Bridget’s affection. Hardly any movies are as endearing as “Bridget Jones’s Diary,” and it boasts one of the most compelling enemies-turned-lovers narratives (a testament to its exceptional source material).

Starring: Renee Zellweger, Colin Firth, Hugh Grant
Directed by: Sharon Maguire
Rating: R (Mature Audiences)
Running Time: 1 hour and 36 minutes
Stream on: HBO Max

This version maintains the original structure but provides a more conversational tone for easier reading.

1. When Harry Met Sally…

As a fervent movie enthusiast, I find it hard to imagine any other ‘enemies-to-lovers’ film surpassing the charm of “When Harry Met Sally…” This timeless classic follows the story of Sally Albright (Meg Ryan) and Harry Burns (Billy Crystal), who, after graduating from college, embark on a road trip from Chicago to New York. From the get-go, they clash profoundly, primarily due to Harry’s claim that men and women can never truly be friends because love always complicates things.

Throughout the film, Sally and Harry’s paths keep intersecting, eventually leading them to conclude that friendship is the way forward. However, as Harry predicted, romance does creep in, causing a stir when they end up sharing an intimate moment together, almost leading them to part ways forever.

1989 saw the release of a remarkable romantic comedy, skillfully directed by Rob Reiner and written by Nora Ephron. Two brilliant New Yorkers, portrayed by Ryan and Crystal, engage in constant squabbles while searching for love, ironically missing out on each other. Notably, Carrie Fisher delivers one of her finest performances outside the “Star Wars” series. If you haven’t watched “When Harry Met Sally…”, make it a priority; its charm will undoubtedly earn it a spot among your all-time favorites by the end of the movie.

Actor Lineup: Meg Ryan, Billy Crystal, and Carrie Fisher
Directed by: Rob Reiner
Rating: Rated (suitable for adults)
Duration: 95 minutes
Streaming Options: Available for purchase or rental

2025-05-18 21:32