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

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

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 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

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 ing 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

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

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).