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.


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.


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

Directed By Donald Petrie

How to Lose a Guy in 10 Days is available to stream on Paramount Plus, Showtime, and Pluto TV.

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 an enemies-to-lovers story. Plus, Kathryn Hahn offers the movie’s best performance despite playing a supporting role.

14 The Hating Game (2021)

Directed By Peter Hutchings

An image of Lucy and Bexley standing in an elevator in The Hating Game

The Hating Game is available to stream on Hulu and Hoopla.

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.

13 Red, White & Royal Blue (2023)

Directed By Matthew Lopez

Red, White & Royal Blue is available to stream exclusively on Prime Video.

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. 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. The chemistry between Perez and Galitzine makes Alex and Henry one of the best enemies-to-lovers couples in movies and TV. 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.

12 The Proposal (2009)

Directed By Anne Fletcher

Margaret (Sandra Bullock) and Andrew (Ryan Reynolds) stand together in her office in The Proposal.

The Proposal is available to rent or purchase on Amazon Video, Apple TV, and YouTube

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. 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

Billy Crystal as Harry Watching Meg Ryan as Sally Fake an Orgasm in When Harry Met Sally

When Harry Met Sally is available to stream on Paramount Plus With Showtime, The Paramount Plus Apple TV Channel, and Showtime

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. 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

10 Things I Hate About You is available to stream on Prime Video and Disney Plus.

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 memorable monologue.

9 It Happened One Night (1934)

Directed By Frank Capra

Clark Gabel and Claudette Colbert look back at each other while in a train car in It Happened One Night.

It Happened One Night is available to rent or purchase on Amazon Video, Apple TV, and YouTube.

One of the oldest and best enemies-to-lovers screwball rom-coms is 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. 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

Ronny and Loretta stand together in formal attire in Moonstruck

Moonstruck is available to stream on multiple platforms, including FuboTV And Paramount Plus With Showtime.

The classic rom-com Moonstruck is vastly underappreciated despite its great enemies-to-lovers storyline. 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. Moreover, Moonstruck’s biggest claim to fame should be that it’s one of Cher’s best movies of all time.

7 His Girl Friday (1940)

Directed By Howard Hawks

His Girl Friday is available to stream on multiple platforms, including Amazon Prime And FuboTV.

One of the best Cary Grant comedies is a screwball enemies-to-lovers rom-com called His Girl Friday. In this film, a newspaper editor named Walter Burns (Cary Grant) 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.

6 27 Dresses (2008)

Directed By Anne Fletcher

Jane and Kevin drinking and singing in a bar in 27 Dresses.

27 Dresses is available to stream on Hulu.

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, whom a journalist named Kevin “Malcolm” Doyle (James Marsden) decides to exploit 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. Plus, the scene of the duo drunkenly singing “Bennie & The Jets” by Elton John is unforgettable.

Related: 10 Beloved Rom-Com Couples That Were Actually Toxic For Each Other

5 The Ugly Truth (2009)

Directed By Robert Luketic

Abby and Mike stand in the elevator while avoiding eye contact in The Ugly Truth.

The Ugly Truth is available to stream on the Starz Apple TV Channel

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 (Katherine 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 enemies-to-lovers rom-coms, The Ugly Truth is her best due to the undeniable chemistry between her and Butler. Plus, the sexual chemistry and explicit scenes add steaminess that’s appealing to many adults.

4 What Happens In Vegas (2008)

Directed By Tom Vaughan

What Happens In Vegas is available to stream on History Vault.

What Happens In Vegas is a classic enemies-to-lovers movie with A+ actors and a stellar soundtrack. After the accidentally-married 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 also includes bangers like “Are You Gonna Be My Girl” by Jet, which increases pacing and drama in an already entertaining movie.

3 America’s Sweethearts (2001)

Directed By Joe Roth

Eddie and Gwen argue in a hotel room while Kiki watches in America's Sweethearts.

America’s Sweethearts is available to stream on Hoopla.

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.

2 You’ve Got Mail (1998)

Directed By Nora Ephron

Kathleen and Joe look out the window of a restaurant in You've Got Mail.

You’ve Got Mail is available to stream on Tubi

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.

Related: Every Tom Hanks & Meg Ryan Movie, Ranked Worst To Best

1 Dirty Dancing (1987)

Directed By Emile Ardolino

Dirty Dancing is available to stream on the Paramount Plus Apple TV Channel.

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. Grey strikes just the right balance between naive and capable, while Swayze goes from brusk to sensitive. 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.