15 Best Enemies-To-Lovers Rom-Com Movies

Summary

• Enemies-to-lovers rom-coms offer zippy dialogue, sexual tension, and relatable conflicts, making them entertaining to watch.
• These movies excel at building compelling character development before the couple gets together, making it easy for viewers to emotionally invest in them.
• Rom-coms like “How to Lose a Guy in 10 Days” and “Red, White & Royal Blue” showcase the enemies-to-lovers trope with excellent chemistry between the characters.

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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.

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15 How to Lose A Guy In 10 Days (2003)

Directed By Donald Petrie

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 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

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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 a 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

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

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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

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.

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

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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

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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 of the duo drunkenly singing “Bennie & The Jets” by Elton John is unforgettable.

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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 in from other more clean-cut movies of the genre, offering some big laughs.

4 What Happens In Vegas (2008)

Directed By Tom Vaughan

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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

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

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 timeunaware 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

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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.

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.

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