The enemies-to-lovers trope is extremely popular with rom-com fans, but some movies do it better than others. Rom-coms have existed in Hollywood for almost as long as movies, with the first two – Sherlock Jr. and Girl Shy – coming out as silent films in 1924. The movies are popular with audiences due to their balanced combination of romance, drama, and comedy. However, the large amount of variation in tropes makes the movies appealing as well.
One of the most popular tropes in rom-com movies is enemies-to-lovers. Enemies-to-lovers rom-coms are the perfect pick to watch after a long week. Movies with this trope include zippier dialogue, sexual tension, and relatable conflicts. These stories function on the premise that there’s a thin line between love and hate. Moreover, the scripts typically have compelling character development before the couple gets together, making it easier to emotionally invest in them. Ultimately, some of the best rom-coms of all time harness this trope, adding their own unique style.
20 Out Of Sight (1998)
Directed By Steven Soderbergh
Out of Sight
Out of Sight is a 1998 crime comedy film directed by Steven Soderbergh. It stars George Clooney as bank robber Jack Foley and Jennifer Lopez as U.S. Marshal Karen Sisco. After escaping from prison, Foley kidnaps Sisco, leading to a complex romance intertwined with the law and crime. The film is adapted from the Elmore Leonard novel and features a blend of action, wit, and sharp dialogue.
- Release Date
- June 26, 1998
- Runtime
- 123 minutes
- Cast
- George Clooney , Jim Robinson , Mike Malone , Donna Frenzel , Manny Suárez , Dennis Farina
While many of the enemies-to-lovers movies find interesting ways to pit the central couple against each other, Out of Sight is one of the few movies that achieves this by putting the characters on the opposite sides of the law. Based on an Elmore Leonard novel, Out of Sight stars George Clooney as a bank robber who escapes from prison and ends up taking a US Marshal (Jennifer Lopez) hostage. While they become separated in the chaos of the escape, a connection is formed which deepens as she continues to hunt him down.
While the crime caper aspects are thrilling, the sparks that fly between Clooney and Lopez are the highlight of the movie.
Out of Sight is one of the coolest movies of all time, with an effortlessly slick style and confident tone pulled off by Steven Soderbergh. While the crime caper aspects are thrilling, the sparks that fly between Clooney and Lopez are the highlight of the movie. The scene with the two of them trapped in a trunk together solidifies the movie’s wonderful ability to pull off this dynamic between natural enemies and strangers who are drawn to each other.
19 Anyone But You (2023)
Directed By Will Gluck
Anyone But You
Anyone But You is a romantic comedy by director Will Gluck starring Sydney Sweeny and Glen Powell. Sweeny and Powell star as Bea and Ben, two strangers with an incredible first date that goes sour following one incident at the tail end. Thinking the worst is behind them, the two are roped into a destination wedding in Sydney, Australia, where they’ll have to pretend to be a couple despite absolutely hating each other.
- Release Date
- December 22, 2023
- Runtime
- 103 minutes
- Director
- Will Gluck
While there are some who have suggested the theatrical rom-com has faded away and the genre can only survive on streaming, Anyone But You served as proof that audiences will show up for an enticing entry in the genre. Glen Powell and Sydney Sweeney solidified their status as the next generation of Hollywood stars. They play two people who hate each other following a romantic misunderstanding only to find themselves in the same wedding party. In order to not ruin the weekend, they decide to pose as a couple.
Powell and Sweeney share wonderful chemistry together, bringing out the laughs in their resentment for each other, while also making the audience root for them as they begin to embrace their obvious attraction for one another. The movie aims to be a throwback to rom-coms of the 90s and 00s and makes the genre proud in the end.
18 Clueless (1995)
Directed By Amy Heckerling
One of the most iconic teen movies of all time also features a truly charming and unexpected enemies-to-lovers romance. Clueless is a modern update of Jane Austen’s Emma with Alicia Silverstone playing Cher, a high schooler who discovers she has a talent for setting people up to meet their true love. However, she soon feels that she owes it to herself to explore her own love life, which leads her somewhere unexpected.
The fact that Cher’s love interest ends up being her older stepbrother (Paul Rudd) does feel odd in retrospect, but the relationship works in the context of the movie. Cher and Josh are very opposite personalities, with Josh being involved in politics and trying to prove himself an adult while Cher is focused on the high school world exclusively. However, seeing them turn their annoyance with each other into a romance is part of what turned Clueless into a true classic.
17 Palm Springs (2020)
Directed By Max Barbakow
Enemies-to-lovers movies often seek out a particularly stressful situation to put two people in that causes them to butt heads. Being stuck in an unending time loop is a good example. Palm Springs stars Cristin Milioti as a woman having a miserable time at her sister’s wedding, only to hit it off with a mysterious guest (Andy Samberg). After spending the night together, she wakes up to discover the day is repeating itself and she has been sucked into the same time loop he has been in for a long time.
It is an outlandish situation that immediately puts them against each other, with Milioti especially having fun with the pure frustration and hate she feels about this horrible situation. However, it is also a blast to see these two coming to terms with being stuck together for eternity and having fun with the endless possibilities.
16 Much Ado About Nothing (1993)
Directed By Kenneth Branagh
William Shakespeare’s work continues to influence rom-coms to this day, so it makes sense that an adaptation of one of his best comedies stands as a great rom-com movie. Much Ado About Nothing is one of Kenneth Branagh’s best Shakespeare adaptations, in which he stars opposite Emma Thompson as two people who have a long and heated history together. With their friends annoyed with their constant fighting, they develop a trick to convince each of them that they are in love with each other.
The movie is a star-studded affair with the likes of Denzel Washington, Michael Keaton, and Keanu Reeves. However, the central romance between Branagh and Thompson is the real treat, with them both excelling at the Shakespearean dialogue and having fun with the endless misunderstandings that put these two on a path to romance.
15 How to Lose A Guy In 10 Days (2003)
Directed By Donald Petrie
How to Lose A Guy in 10 Days, directed by Donald Petrie, is a romantic comedy starring Kate Hudson and Matthew McConaughey. The film follows a magazine writer and an advertising executive, each with conflicting personal agendas, as they navigate the complexities of a burgeoning relationship. Through humorous situations and romantic entanglements, the narrative explores themes of love, deception, and the challenges of modern dating.
- Director
- Donald Petrie
- Release Date
- February 7, 2003
- Runtime
- 116 minutes
One of the most entertaining enemies-to-lovers rom-coms is How to Lose a Guy in 10 Days. This film pits Andie Anderson (Kate Hudson), a journalist writing an article on how to drive a man away, against Benjamin Berry (Matthew McConaughey), a writer who bets he can make any woman fall in love with him. Both go up against a 10-day deadline, making the stakes higher. Andie and Ben go to great lengths to achieve their goals, creating the tension and repartee typical of these movies.
This is a common dynamic in the enemies-to-lovers stories with the couple initially seeing each other as a means to an end only to find themselves falling for each other despite their initial plans. Hudson and McConaughey have terrific chemistry to make them an ideal duo. Plus, Kathryn Hahn offers the movie’s best performance despite playing a supporting role.
14 The Hating Game (2021)
Directed By Peter Hutchings
The Hating Game
The Hating Game is a romantic comedy based on the novel by Sally Thorne. Released in 2021, the film stars Lucy Hale as Lucy Hutton and Austin Stowell as Joshua Templeman, two competitive coworkers at a publishing company who enter a ruthless game of one-upmanship. Directed by Peter Hutchings, the narrative explores the fine line between love and hate as the protagonists navigate their evolving relationship amidst office antics.
- Director
- Peter Hutchings
- Release Date
- December 10, 2021
- Cast
- Lucy Hale , Yasha Jackson , Austin Stowell , Tania Asnes , Sakina Jaffrey , Corbin Bernsen , Billy Thomas , Brock Yurich , Damon Daunno
- Runtime
- 102 minutes
The Hating Game is a fantastic modern addition to the enemies-to-lovers trope. In this movie, Lucy Hutton’s (Lucy Hale) and Josh Templeman’s (Austin Stowell) publishing houses merge, meaning the pair must compete for the same promotion. Their working relationship becomes even more complicated after the pair develop an attraction to each other.
Lucy and Josh’s superb chemistry makes them easy to root for. Moreover, The Hating Game’s script perfectly adapts the eponymous book by Sally Thorne, capturing all the witty banter. The workplace setting for these types of stories is another common element as it creates a different type of tension that also allows for some competition between the would-be lovers. Once a romance develops, it introduces another element as they will have to make a decision about whether their career or relationship is more important.
13 Red, White & Royal Blue (2023)
Directed By Matthew Lopez
Red, White & Royal Blue is a romantic comedy film based on the New York Times best-selling novel by Casey McQuiston. The film follows the President of the United States son, Alex, and Britain’s Prince Henry, who are at odds over nearly everything. However, the two get into an altercation at a significant event, further causing a divide between the two nations; they are forced to reconcile their differences on paper. But as the two spend time together, their rivalry evolves into something more.
- Director
- Matthew Lopez
- Release Date
- August 11, 2023
- Runtime
- 121 Minutes
Based on the New York Times best-selling novel by Casey McQuiston, Red, White & Royal Blue brings an LGBTQ+ enemies-to-lovers story to life. It also brings in another audience with its story taking place within the world of royals and politicians. After the US president’s son, Alex Claremont-Diaz (Taylor Zakhar Perez), gets into a fight with a British royal, Prince Henry (Nicholas Galitzine), the pair must pretend to be friends to repair their public image.
On top of this, the writing in Red, White & Royal Blue does an excellent job of capturing queer experiences without leaning too far into stereotypes. It is also sweet to see how, despite these two hating each other, to begin with, they soon discover that they have a lot in common and understand each other’s struggles better than anyone else could.
12 The Proposal (2009)
Directed By Anne Fletcher
Though Ryan Reynolds’s movies tend to be more action comedies these days, there was a time when he was more known for his career in rom-coms. The Proposal follows a New York City publisher named Margaret Tate (Sandra Bullock) who forces her assistant Andrew Paxton (Ryan Reynolds) to fake-marry her for a green card, but their lie quickly spirals out of control.
This phenomenal enemies-to-lovers rom-com is fast-paced and filled with punchy dialogue. Like many approaches to the genre, there is an implausible sitcom scenario to set things up, but it makes way for a great mix of comedy and humor. The characters in this story walk the line between obnoxious and loveable due to the incredible performances by big-name actors. Ultimately, the cast, script, and direction make The Proposal one of the best rom-coms ever.
11 When Harry Met Sally (1989)
Directed By Rob Reiner
Written by Nora Ephron and directed by Rob Reiner, When Harry Met Sally chronicles the life and relationship of Harry Burns and Sally Allbright, who meet just after college on a road trip to New York City and begin a decade-long relationship that slowly evolves from friendship to true love. Billy Crystal and Meg Ryan star as Harry and Sally, with a further cast that includes Carrie Fisher and Bruno Kirby.
- Director
- Rob Reiner
- Release Date
- July 21, 1989
- Cast
- Bruno Kirby , Meg Ryan , Carrie Fisher , Steven Ford , Billy Crystal
- Runtime
- 95 minutes
Meg Ryan is a rom-com superstar, but her best film will always be When Harry Met Sally. The film spans 12 years, exploring the eponymous combatants as they develop a friendship rife with sexual chemistry. When Harry Met Sally builds the tension so well that it feels like a relief when the pair finally profess their feelings.
It is a lot of fun seeing this relationship develop over a long period with it initially starting with the duo as two strangers who almost immediately cannot stand each other only to find a bond grow over the course of some time. In fact, it is not only an enemies-to-lovers story, but also a friends-to-lover story. Additionally, the movie incorporates one of the funniest and most iconic rom-com scenes in which Sally (Meg Ryan) fakes an orgasm in a deli to prove a point to Harry (Billy Crystal).
10 10 Things I Hate About You (1999)
Directed By Gil Junger
Based on Shakespeare’s The Taming of the Shrew, 10 Things I Hate About You is a modern retelling of the classic play, set against the backdrop of a 90s Seattle high school. When social outcast Patrick Verona is paid to try and win over antisocial Kat Stratford in order so her younger sister will be allowed to date, he and Kat find an unexpected connection forming between them. Julia Stiles and Heath Ledger star as Kat and Patrick, with a further cast that includes Joseph Gordon-Levitt, Larisa Oleynik, David Krumholtz, Andrew Keegan, and Larry Miller.
- Director
- Gil Junger
- Release Date
- March 31, 1999
- Cast
- Julia Stiles , Heath Ledger , Joseph Gordon-Levitt , Larisa Oleynik , Larry Miller , Andrew Keegan , David Krumholtz , Susan May Pratt
- Runtime
- 97 minutes
William Shakespeare is famous for his enemies-to-lovers couples, so it’s unsurprising that one of the best rom-coms with this trope is a modern adaptation of The Taming of the Shrew. In 10 Things I Hate About You, Patrick (Heath Ledger) – the bad boy of Padua High School – gets paid to date Kat (Julia Stiles) – the combative ice queen. Though their relationship starts contentious, the pair begin developing real feelings for one another.
On top of embodying the enemies-to-lovers trope, 10 Things I Hate About You includes relatable themes, a strong woman protagonist, and a fun young cast that also includes Joseph Gordon Levitt and David Krumholtz. However, it is Stiles and Ledger who steal the show and become breakout stars as two characters who don’t fall into the stereotypical teen rom-com archetypes and feel like fresh, relatable personalities.
9 It Happened One Night (1934)
Directed By Frank Capra
It Happened One Night is a 1934 romantic comedy directed by Frank Capra. The film follows the adventures of a runaway heiress, played by Claudette Colbert, who teams up with a charming but out-of-work reporter, portrayed by Clark Gable. Their journey is marked by humorous and heartfelt moments that challenge social conventions and lead to unexpected romance.
- Director
- Frank Capra
- Release Date
- February 22, 1934
- Runtime
- 105 Minutes
- Cast
- Clark Gable , Claudette Colbert , Walter Connolly , Roscoe Karns
There is a tendency to look at the enemies-to-lovers trend of storytelling in rom-coms as a more modern development in Hollywood, but there are many examples of it in older movies as well, including It Happened One Night. In this film, an out-of-work reporter named Peter Warne (Clark Gable) strong-arms an heiress, Ellie Andrews (Claudette Colbert), into giving him an exclusive story in exchange for assistance getting to her husband. Peter and Ellie butt heads and can’t stop bickering, but they have an undeniable chemistry that drives them together.
These classic Hollywood romance movies stood the test of time for a reason and It Happened One Night is still regarded as one of the best movies of all time. With its charming plot and loveable characters, It Happened One Night is a must-watch for rom-com fans.
Clark Gable is best known for playing Rhett Butler in
Gone With the Wind.
8 Moonstruck (1987)
Directed By Norman Jewison
The classic rom-com Moonstruck is vastly underappreciated and shows the kind of level the genre can be elevated to with some truly great writing and performances. In this movie, Loretta (Cher) runs into trouble when she tries to convince her fiance’s surly brother, Ronny (Nicolas Cage), to attend the wedding. Loretta and Ronny couldn’t be less similar, making it interesting when they develop feelings for each other.
One of Cher’s best movies of all time
This film is a classic enemies-to-lovers story, but it deserves more credit for its script and cinematography. The moment Ronny confesses that he is in love with Loretta only for her to hilariously tell him „Snap out of it!” is the kind of terrific unexpected vibe of the movie. Moreover, Moonstruck’s biggest claim to fame should be that it’s one of Cher’s best movies of all time with the superstar winning the Oscar for Best Actress for her funny, heartfelt, and authentic portrayal.
7 His Girl Friday (1940)
Directed By Howard Hawks
His Girl Friday
His Girl Friday is a 1940 film directed by Howard Hawks, featuring Cary Grant as wily newspaper editor Walter Burns. Desperate to retain his star reporter and estranged wife, played by Rosalind Russell, Burns concocts a scheme to keep her from leaving journalism for a new suitor by exploiting her passion for a major news story.
- Director
- Howard Hawks
- Release Date
- January 18, 1940
- Cast
- Cary Grant , Rosalind Russell , Ralph Bellamy , Gene Lockhart
- Runtime
- 92 minutes
One of the best Cary Grant comedies is a screwball enemies-to-lovers rom-com called His Girl Friday. From legendary director Howard Hawks, the movie follows a newspaper editor named Walter Burns (Cary Grant) who tries to keep his ex-wife and star investigative reporter, Hildy (Rosalind Russell), from remarrying by distracting her with a significant story.
Contentious exes provide the lifeblood of the enemies-to-lovers trope, and Walter and Hildy in His Girl Friday are the best pair. They bounce off each other with banter and wit, only made stronger by their intense chemistry. The movie has been praised for having some of the best dialogue of all time with the conversations between the two characters doing a great job of highlighting the ways in which they cannot stand each other as well as how it is inevitable that they will fall for each other.
6 27 Dresses (2008)
Directed By Anne Fletcher
27 Dresses
27 Dresses is a romantic comedy film directed by Anne Fletcher, starring Katherine Heigl as Jane Nichols. Released in 2008, the film follows Jane, a perpetual bridesmaid who has served in 27 weddings. Her steadfast commitment is tested when her sister becomes engaged to the man Jane secretly loves. The film explores themes of love, self-discovery, and personal growth.
- Director
- Anne Fletcher
- Release Date
- January 10, 2008
- Cast
- Brian Kerwin , Charli Barcena , Peyton List , Jane Pfitsch , Katherine Heigl , Jennifer Lim
- Runtime
- 107 minutes
The classic rom-com 27 Dresses centers on Jane Nichols (Katherine Heigl), a chronic bridesmaid who must take on the role again with her sister and her boss, when a journalist named Kevin “Malcolm” Doyle (James Marsden) decides to exploit her for a story. While Kevin and Jane are never fully enemies in 27 Dresses, they still align with the trope due to their constant bickering and pushing each other’s buttons. They go through a compelling arc, developing a romantic connection over time.
Heigl was known for her many rom-coms earlier in her movie career, but 27 Dresses remains the most popular of them all. Though it doesn’t break new ground, Jane and Kevin make for an entertaining pair that the audience will really want to see get together no matter how obvious it is. Plus, the scene where the duo drunkenly sings “Bennie & The Jets” by Elton John is unforgettable.
5 The Ugly Truth (2009)
Directed By Robert Luketic
Another example of Katherine Heigl’s brief reign over the rom-com genre, The Ugly Truth is a hilariously raunchy enemies-to-lovers rom-com that is equal parts funny and sexual. In this film, a hopeless romantic TV producer named Abby Richter (Heigl) gets paired up with a TV celebrity named Mike Chadway (Gerard Butler), who believes he knows everything women and men want from each other.
While Heigl has appeared in numerous worthy leading men in the rom-com genre, The Ugly Truth features one of her best with the undeniable chemistry between her and Butler who is also a surprisingly successful actor in the genre despite his reputation for action movies. Plus, the sexual chemistry and explicit scenes add steaminess that’s appealing to many adults while the R-rated helps to separate it from other more clean-cut movies of the genre, offering some big laughs.
4 What Happens In Vegas (2008)
Directed By Tom Vaughan
What Happens in Vegas is a romantic comedy starring Cameron Diaz and Ashton Kutcher as two strangers who impulsively marry after a wild night in Las Vegas. When one of them wins a large jackpot, the pair is forced to stay married and attempt to make their relationship work to claim the prize. The film explores themes of love, chance, and the consequences of impetuous decisions.
- Director
- Tom Vaughan
- Release Date
- May 9, 2008
- Runtime
- 99 minutes
What Happens In Vegas is a classic enemies-to-lovers movie with A+ actors and a stellar soundtrack. After they accidentally get married during a wild Las Vegas trip, Joy McNally (Cameron Diaz) and Jack Fuller (Ashton Kutcher) win the jackpot in a Vegas casino, a judge compels them to live together as a couple for six months in order to get a divorce and keep the money. In addition to the leading duo, the cast includes Rob Corddry, Lake Bell, Jason Sudeikis, and Dennis Farina.
What Happens In Vegas is another rom-com that requires a lot of suspension of disbelief in its premise with it sounding more like a 90s sitcom idea than something that would actually happen in real life. However, it provides a solid reason to have these two actively working against each other. It gives a nice edge to the characters, with them taking their status as enemies to some funny extremes and making their eventual romance even more rewarding.
3 America’s Sweethearts (2001)
Directed By Joe Roth
America’s Sweethearts is a comedy film directed by Joe Roth, starring Julia Roberts, Billy Crystal, Catherine Zeta-Jones, and John Cusack. The plot revolves around a press junket for a film featuring a once-popular celebrity couple who have recently separated. Amidst the chaos, their personal and professional relationships are put to the test, leading to humorous and poignant moments.
- Director
- Joe Roth
- Release Date
- July 20, 2001
- Runtime
- 102 Minutes
A star-studded cast leads this underseen rom-com that features the added twist of being set within the world of movie stars. Unlike other rom-com movies that include a clear enemies-to-lovers storyline, America’s Sweethearts is an exciting twist on this trope. After their messy divorce, actors Eddie (John Cusack) and Gwen (Catherine Zeta-Jones) must get through one last press junket pretending to be together, assisted by Gwen’s sister, Kiki (Julia Roberts), and a press agent named Lee (Billy Crystal).
This movie fakes viewers out by promoting the enemies-to-lovers trope but switching it around at the last second. As such, it’s an excellent way to achieve this trope while also seeing the underdog win in the end. It is a funny Hollywood satire that features a lot of colorful characters in its large cast while also delivering a solid romance between some of the biggest names in the business.
2 You’ve Got Mail (1998)
Directed By Nora Ephron
You’ve Got Mail
Directed by Nora Ephron, You’ve Got Mail follows Joe and Kathleen, two strangers who meet in an AOL chatroom and begin a relationship over email, unaware that they are actually a lot more connected to one another than they think. Tom Hanks and Meg Ryan star as Joe and Kathleen, with a further cast that includes Parker Posey, Jean Stapleton, Dave Chappelle, and Greg Kinnear.
- Director
- Nora Ephron
- Release Date
- December 18, 1998
- Runtime
- 119 minutes
Tom Hanks and Meg Ryan are often regarded as one of the best rom-com duos of all time, and while this may not be regarded by all as their best movie together, it is a great display of that amazing chemistry. The enemies-to-lovers rom-com You’ve Got Mail includes dramatic irony, which sets the movie apart from other additions to the subgenre. You’ve Got Mail tells the story of a book superstore owner named Joe Fox (Tom Hanks) who develops a romance over the internet with a small bookshop owner named Kathleen Kelly (Meg Ryan), not knowing they are rivals.
Because Joe and Kathleen spend most of their time unaware of their enemies-to-lovers situation, viewers get an extra layer of intrigue. This dramatic irony allows viewers to know what’s coming before the characters do in You’ve Got Mail.
1 Dirty Dancing (1987)
Directed By Emile Ardolino
Dirty Dancing
Starring Patrick Swayze and Jennifer Grey, Dirty Dancing follows Frances „Baby” Houseman, a young woman on vacation at a summer resort with her family who becomes the unwitting competition partner of one of the resort’s dance instructors, Johnny. As Baby and Johnny’s relationship deepens over the course of the summer, the disapproval of Baby’s family, especially her father, threatens to tear them apart.
- Director
- Emile Ardolino
- Release Date
- August 21, 1987
- Runtime
- 100 minutes
The classic enemies-to-lovers rom-com Dirty Dancing exceeds all expectations due to the phenomenal acting, a quotable script, and an unforgettable ending. This film follows Johnny (Patrick Swayze), a dance instructor, who enlists Baby (Jennifer Grey), a young woman spending the summer with her family in the Catskills, as a dance partner. It makes for one of the best dance movies of all time while also depicting a romance that remains a fan-favorite among many audiences.
Baby and Johnny’s dance at the
end of
Dirty Dancing
is also so iconic it has been recreated in multiple movies and TV shows
Grey strikes just the right balance between naive and capable, while Swayze goes from brusk to sensitive in one of his most iconic roles. Lines like “nobody puts baby in a corner” have become part of the pop culture zeitgeist. Baby and Johnny’s dance at the end of Dirty Dancing is also so iconic it has been recreated in multiple movies and TV shows.