Best Romance Movies Where Enemies Become Lovers, Ranked

Summary

• Enemies-to-lovers trope shines in rom-coms like “The Hating Game” and “When Harry Met Sally…”
• Anne Hathaway’s charming rom-com roles in “Ella Enchanted” and “The Princess Diaries 2” stand out.
• Legendary classic rom-coms like “Pride and Prejudice” and “It Happened One Night” set the standard for the genre.

Within the romance genre, you have your fair share of tropes. The third-act breakup that occurs when the two lovers have a huge fight when the movie is almost over before dramatically getting back together. The scene in which person A runs through an airport to get to person B before they board their plane, and always makes it. Or the two best friends who swear they see each other as siblings but secretly harbor romantic feelings. Tropes any romance lover knows well enough since they’re constantly used in these classic rom-coms.

There’s only one trope that doesn’t ever seem to get old if it’s done right, and that’s the enemies-to-lovers storyline. Two people who genuinely can’t stand each other and bicker more than they have normal conversations, but somehow end up falling in love. Let’s take a look at the best romance movies that depict the enemies-to-lovers trope.

20 Ella Enchanted (2004)

Anne Hathaway makes it on this list twice, once as a queen and the other as Ella in Ella Enchanted. Since she was a baby, Ella was cursed by a spell that made her unable to use free will. In the land in which this story takes place, there are all types of creatures that inhabit the area, such as elves, ogres, and even giants. Of course, there’s a famous prince who’s beloved by almost everyone he meets and is portrayed as a heartthrob by his loyal fan base. When Ella and Char meet, the prince is shocked to learn that she’s not charmed by his good looks and treats him as if he were anyone else.

Hathaway Is a Rom-Com Legend

Throughout the film, they have their moments where their arguing gets them into tough situations, such as singing in front of a bunch of giants and fighting off evil step-sisters. As time goes on, Ella and Char realize they don’t detest each other as much as they thought, and end up getting their happily ever after. Hugh Dancy and Anne Hathaway also make a really adorable couple who love to bicker but also always have each other’s backs. Stream on Paramount+ and DirecTV.

19 Anyone But You (2023)

Sydney Sweeney, whom you might know from Euphoria, starred in the enemies-to-lovers, fake-dating rom-com Anyone but You alongside Glen Powell. It tells the story of Bea and Ben, who meet and have an amazing first date, but then become estranged due to a misunderstanding. When Bea’s sister is all set to marry Ben’s best friend’s sister, the two of them are forced into the same place again. Bea and Ben make a deal to fake-date each other during the wedding to placate their nosy families but sparks fly alongside fiery insults that make them both rethink their decision.

Uses Tropes in all the Right Ways

Sydney Sweeney has proved herself to be capable of great things and this movie proves that she is great at the tried and tested field of rom-com. Glen Powell’s character compliments her Bea perfectly, and they make us wish we were also on a romantic wedding getaway with our frenemy. Their arrangement makes it hard for them to not feel their sexual tension. The events leading up to their final reconciliation make the grand gesture sweet and totally worthwhile. Not yet available to stream.

18 Red, White and Royal Blue (2023)

Red, White and Royal Blue quickly became a sensation when the novel was released by Casey McQuinston in 2019, dominating the bestseller list and was in talks of being adapted into a film not long after its release. This sweet story focuses on two individuals, Prince Henry from Britain and Alex Claremont-Diaz, the son of the President of the United States. The animosity between the two quickly turns into heated love when a misunderstanding clears up.

A Lovable and Charming Romance

When Alex and Henry first meet at a royal wedding, things get off to a rough start as they fight and ruin the wedding cake, quickly establishing the enemies part of this trope. However, as the two are forced to spend more time together, they then realize that they secretly really enjoy each other, and once they enter a friends-with-benefits relationship, things get incredibly messy for the two. Starring Taylor Zakhar Perez as Alex and Nicholas Galitzine as Henry, this movie quickly made a lot of fans across the globe. Stream on Prime Video.

17 Life as We Know It (2010)

In Life as We Know It, we see Josh Duhamel and Katherine Heigl as Eric and Holly, who hate each other with a passion after their best friends Alison and Peter try to set them up on a blind date. Peter and Alison get married and have a baby daughter. But tragedy occurs when they are killed in a car crash and godparents Eric and Holly are forced to live together and take care of her. But when they put their differences aside for little Sophie, they discover romantic feelings underneath all that animosity.

For the Forced Proximity Lovers

The film takes full advantage of the enemies-to-lovers and forced proximity tropes. If Eric and Holly were never forced to live together, they probably would have spent the rest of their lives hating each other, but that does not happen. Heigl and Duhamel do a fantastic job of first hating and then loving each other and their chemistry is so palpable you can feel the tension through the screen. Throw an adorable child in the mix and you have got yourself a great rom-com. You’ll laugh, you’ll cry, and you’ll swoon at Life as We Know It. Stream on Max.

16 The Bounty Hunter (2010)

Gerard Butler is on this list twice, and it’s been years since Butler has been in a rom-com; what’s up with that? The Bounty Hunter follows a divorced couple, Nicole (Jennifer Aniston) and Milo (Butler). Milo is an ex-police officer turned bounty hunter who is tasked to retrieve Nicole, his ex and an investigative reporter, when she skips her bond hearing, revoking her bail. But when Milo catches up to Nicole and captures her, they get into a load of trouble with the people whom Nicole is investigating.

Enemies-to-Lovers With Added Action

Aniston and Butler are great and hilarious together as Nicole constantly slips out of Milo’s grasp, but Milo always manages to catch up with her, no matter what she tries. They get caught up in some shady things, and as they work together to make it out alive, they come to the conclusion that they both have unresolved feelings for each other. Estranged couples have always been the lifeblood of enemies-to-lovers movies and even though this film is more of an action comedy, the two main characters make for a hilariously adorable couple we cannot help but love. Stream Prime Video.

15 The Proposal (2009)

The Proposal is the classic story of a marriage of convenience, but with real feelings at the end of it, which we love. Ryan Reynolds and Sandra Bullock have so much chemistry, and they’re both so hilarious, that it makes them a great duo in this rom-com. What starts off as a tense work relationship between a hardheaded boss and her assistant, morphs into a full-fledged romance as they rush to get married, to save Susan (Bullock) from leaving the country.

Incredible Chemistry from the Leads

The fact that the two main characters are so different in nature only makes this movie more entertaining. We get to see how the two of them learn more about each other and slowly start falling head-over-heels in love. The late Betty White plays a hilarious character, and there are so many memorable scenes, that this movie is perfect if you need a pick-me-up. Stream on Hulu, FuboTV, and DirecTV.

14 Hum Tum (2004)

Even though there is an abundance of rom-coms in Bollywood, none of them nailed the enemies-to-lovers trope quite like Hum Tum. It tells the story of Riya and Sameer, who meet on a plane and end up spending a day when their flight stops in Amsterdam. Cartoonist Sameer, who is a carefree playboy, realizes that he feels a connection towards Riya even though her serious disposition is vastly different from his personality. They part ways on a bitter note, but over the years, fate keeps bringing them together until they cannot deny their love for each other anymore.

A Fated Romance

The film stars Rani Mukherjee as Riya and Saif Ali Khan as Sameer, who have great chemistry on screen even when they are annoyed with each other. Sameer accompanies Riya during some of her happiest days and stays beside her to console her during her heartbreak. The best thing about their movie is the realistic pace with which their relationship moves and it makes their final confession that much sweeter. Stream on Prime Video.

13 The Princess Diaries 2: The Royal Engagement (2004)

Anne Hathaway will forever be known as the Queen of Genovia, and we’re hoping at some point we’ll get a third movie to catch up with Mia. After she’s crowned in the first film, we come back in the second movie to find out she needs to be married in one month. As she’s courted by dozens of eligible bachelors, she meets Prince Nicolas, who’s different from the others, and not in a good way. He and his uncle come to Genovia for sinister reasons, and as Nicolas tries to get under Mia’s skin and work his way into the title of king, the two come to realize they like each other more than they originally thought.

A Timeless Classic Teen Rom-Com

It’s a great follow-up to the first film, and the budding romance between Nicolas and Mia is a fantastic build-up. The two of them already had some chemistry in the first film, but things get even more heated and interesting in Princess Diaries 2: Royal Engagement. The small instances where we see Nicholas falling more and more due to Mia’s kind heart and respecting her as a ruler make us swoon. The scene where Nicholas professes his love for Mia is one of the classic proposal scenes every girl dreamed of in their childhood. Stream on Disney+.

12 The Ugly Truth (2009)

Katherine Heigl and Gerard Butler star in the 2009 rom-com The Ugly Truth, directed by Robert Luketic. It features Abby (Heigl), a morning TV show producer who has bad luck in love but never stops believing in it. Following a drop in her show’s ratings, the company decides to add Mike Chadway (Butler) to the team, a man with a totally different stance on love who she dislikes from the get-go. To settle things between them, Abby and Mike come to an agreement: if he manages to help her win over her crush with his skills as a heartthrob, she will stop treating him badly at work. Otherwise, Mike must quit the show and leave without looking back.

A Chaotic Plot and Electric Chemistry

Whenever there is a bet involved in a rom-com, we can already predict the chaos that is bound to follow, and this film is no different. Even though Abby and Mike are determined to prove each other wrong, they cannot focus on their task when their incredible chemistry and sexual tension blur the lines they draw in their contentious relationship. Heigl and Butler make a great pair whose chemistry makes it the favorite rom-com of a lot of people. Stream on FuboTV, DirecTV, and Starz.

11 Me Before You (2016)

Me Before You is the 2016 film that marked Thea Sharrock’s directorial debut. In it, the enemies-to-lovers dynamic takes a slight twist, as the disdain comes from only one of the main characters. Me Before You features Lou, a hard-working young woman who lands a job as a caregiver to Will, a man who was paralyzed after an accident. Will’s cynical and enraged attitude clashes with Lou’s cheerful optimism, and she makes it her personal mission to prove to this man that life is meant to be lived. Naturally, time will change their feelings as they embark on the most important relationship of their lives.

A More Emotional Offering

Emilia Clarke and Sam Claflin star in this romantic film, joined by Janet McTeer, Charles Dance, Steve Peacocke, and Matthew Lewis. The film has a bittersweet ending that leaves the audience in tears. Clarke and Claflin’s growing love is so heartwarming that the ending hits us harder. However, it is a great story of living your life and going into your death with dignity and surrounded by the people you love and is definitely worth a watch. Rent or buy on Apple TV.

10 The Hating Game (2021)

Characters going from enemies to lovers is, quite literally, the premise of The Hating Game. This Peter Hutchings film is based on Sally Thorne’s novel of the same name and stars Lucy Hale and Austin Stowell as the leads. It features Lucy and Joshua, two employees whose personalities don’t match and who can’t stand each other but are forced to co-exist in the same office after the publishers where they work merge. When the company announces the opening of a new management position, they both see an opportunity to grow in their careers and are willing to do anything to land the job.

Everything You Love About the Trope in One

The Hating Game is basically the enemies-to-lovers trope come to life. Pair that with Lucy and Josh’s all-out office battle about one-upping each other, and you have a sweet and funny rom-com with some steamy tension that you can swoon over. Hale and Stowell are also incredible, as their energies match each other on the screen extremely well. Their journey from hating each other to being attracted to each other to finally falling in love will have you squealing with joy. Stream on Hulu.

9 Clueless (1995)

Clueless is one of the most popular teen films in history, which, after its release in 1995, launched to fame young actors Alicia Silverstone, Stacey Dash, Brittany Murphy, and Paul Rudd, who made his film acting debut in it. Clueless is written and directed by Amy Heckerling and follows Cher, a popular and fashionable high school girl on a mission: giving Tai, a shy new student, a complete makeover in order to help her improve her self-esteem. However, amidst all this, Cher will have to deal with her feelings for Josh, her father’s obnoxious ex-step-son, who is slowly starting to grow on her.

Romantic and Hilarious in Equal Measure

In the film, Josh and Cher are very different in nature and in their outlook on life. But their journey throughout the film to be more understanding towards each other is what makes them fall in love and makes it a great romance story. When Cher realizes that she is in love with Josh after her friend asks her to hook her up with him, is a really cute turning point in the film. Silverstone and Rudd also make a really sweet couple on screen. Stream on FuboTV and Paramount+.

8 Palm Springs (2020)

Palm Springs is one of the more recent productions on this list, a film that marked Max Barbakow’s directorial debut in 2020. It stars Andy Samberg and Cristin Milioti as Nyles and Sarah, two young people who meet while attending a wedding in Palm Springs and, as fate would have it, end up falling into a time loop and reliving the same day over and over again. Faced with this awkward situation, the two must team up to find a way out, although this may not be quite as simple as it seems.

One of the Best Recent Rom-Coms

J.K. Simmons, Peter Gallagher, Meredith Hagner, Camila Mendes, and Tyler Hoechlin join the leads in this production that made its debut at the Sundance Film Festival to great acclaim, and went on to garner, among other accolades, the Independent Spirit Award for Best First Screenplay. Nyles and Sarah are not enemies in the literal sense of the word, but they butt heads in the movie quite a few times, even when they start falling in love. The movie is a great reiteration of the time-loop concept and because of its heart-touching romance. Stream on Hulu.

7 How to Lose a Guy in 10 Days (2003)

The 2003 rom-com classic How to Lose a Guy in 10 Days features Kate Hudson and Matthew McConaughey as Andie and Benjamin, who both make a bet with their friends. Andie bets her heartbroken friend, who is often quite clingy in her relationships, that she can drive away a guy within 10 days by behaving like him. Benjamin, on the other hand, makes a bet that he can make any girl fall for his charms. When the two set their eyes on each other, their chemistry flies off the charts even though both of them try to focus on the ongoing bets.

An Early 2000s Classic

In the movie, Andie and Benjamin are not exactly enemies, but both of them hide ulterior motives at the beginning. The scenes where Andie tries to drive him away while Benjamin tries his best to charm her are truly hilarious and make for a great time. Their argument and reconciliation make the film worth watching a hundred times over. Stream on FuboTV and Paramount+.

6 You’ve Got Mail (1998)

Tom Hanks and Meg Ryan are the dynamic duo when it comes to rom-coms, and You’ve Got Mail is one of the greats. Two strangers become pen-pals over email and get rather close as they swap stories and become emotionally invested in each other’s lives. Meanwhile, in real life, they can’t stand each other. Kathleen is an independent bookshop owner, and Joe is in the big box store business, and the two go head-to-head when Joe sets out to open a huge bookstore that’s right around the corner from Kathleen’s shop. When Joe finds out that his mystery pen-pal is his so-called arch nemesis, things become messy, complicated, and downright romantic.

Hanks and Ryan Are the Best Around

You cannot make an enemies-to-lovers movie list without You’ve Got Mail. Meg Ryan and Tom Hanks have a sweet and incredible chemistry on screen which makes us laugh as they butt heads in real life and dote on each other through emails. But it becomes even more interesting when Joe and Kathleen start falling for each other, even in real life. Add a cute little dog in the mix and you have got a recipe for success. Rent or buy on Apple TV.

5 10 Things I Hate About You (1999)

10 Things I Hate About You is the teen movie that launched Heath Ledger and Julia Stiles to stardom, a production that became a cult classic with fans worshipping it to this day. This 1999 Gil Junger film features Cameron, a student who has just entered Padua High School and right away develops a crush on Bianca, the most popular girl in school. As much as he wants to ask her out, her father’s strict rules prohibit him from doing so: Bianca can’t date boys if her older sister Kat won’t, and the latter is the kind of girl everyone is afraid of. Cameron, who is far from giving up, hires Patrick, the school’s bad boy, to try to conquer Kat, a difficult task that ends in the way they least expect.

A Beloved Performance From Ledger

Rounding out the cast of this rom-com are Joseph Gordon-Levitt, Larisa Oleynik, Larry Miller, Andrew Keegan, and Allison Janney. Kat and Patrick are not enemies, but they are both outcasts in the school. Due to the deal, Patrick starts to romance her out of obligation but ends up falling in love with Kat’s hidden charms and her smart mouth. Kat ends up hating him for a while when she discovers the bet, but in the end, they make up and begin an adorable high school romance just like Cameron and Bianca. The film has become a fan favorite due to its fantastic cast. Stream on Disney+ and Hulu.

4 When Harry Met Sally… (1989)

Now for one of the most iconic couples in the history of rom-coms, Harry and Sally. 1989 marked the premiere of When Harry Met Sally…, a Rob Reiner film written by Nora Ephron and starring Meg Ryan and Billy Crystal in the lead roles. In it, the audience follows the relationship between Harry and Sally, two college students with very different personalities and opinions that cause them to clash almost from the moment they meet. Over the years, the two run into each other again on several occasions, and their relationship evolves as they discover they have more things in common than they thought.

Iconic, Legendary, Unbeatable

If you like slow-burn romances, then you are going to love this film as it takes Harry and Sally twelve years to realize their love and finally get together. Their constant bickering even when they start falling for each other makes this movie interesting and lovable. When Harry Met Sally… became a box-office hit and earned many accolades. Among them, Ephron was nominated for Best Screenplay at the Academy Awards and the lead actors received nominations for Best Actress and Best Actor at the Golden Globes. Rent or buy on Apple TV.

3 Pride and Prejudice (2005)

How could we not include the great Jane Austen adaptation, Pride and Prejudice? The pining, oh, the pining! Matthew McFadyen is without a doubt the best portrayal of Mr. Darcy, with his angst-filled looks and stuttering when he talks to Elizabeth. Like any great classic revolving around love, the two characters detest each other so much upon their first meeting. They both land some harsh insults at each other, but you can practically feel the tension between them as the “hate” starts to morph into longing.

There’s a Reason it’s Been Popular For Centuries

Every interaction between Lizzie and Darcy is carefully orchestrated here. From the moment in which Darcy flexes his hand after helping Lizzie into a carriage to his final confession of love, it’s all bursting with emotion. Another brilliant slow-burn story, it’s worth every second. The film is without a doubt the best on-screen adaptation of the beloved enemies-to-lovers classic novel. Stream on Peacock.

2 Much Ado About Nothing (2012)

Joss Whedon’s black-and-white romantic comedy Much Ado About Nothing is a modern-day retelling of the Shakespeare play of the same name. It is largely unchanged from the original (including the dialogue) and yet jarringly contemporary, using modern clothing and settings. The film reunites Angel stars Amy Acker and Alexis Denisof as the famous Beatrice and Benedict, arguably the most famous pair of “enemies to lovers” in literary history. The movie was filmed in Whedon’s home over the period of 12 days and has a casual, sexy magic to it.

An Intriguing Mix of New and Old

Fans of classical literature who enjoyed the Shakespeare play will enjoy the narrative and pacing of the film. The banter between Beatrice and Benedict throughout the movie is really enjoyable as the audience can see them falling in love through their fights. The second couple, featuring Hero and Claudio, is also really adorable and brings a breath of fresh air to the film. Stream on Plex or rent on Apple TV.

1 It Happened One Night

“The King of Hollywood” Clark Gable appeared alongside Claudette Colbert in the classic 1934 romantic comedy It Happened One Night, in which the legendary actor portrays the cynical reporter Peter Warne, who falls for spoiled heiress Ellie Andrews after agreeing to help reunite her with her conniving husband in return for an exclusive story.

The Original Rom-Com

It Happened One Night features a couple whose antics you cannot help but love. Peter and Ellie fall in love with each other during their adventure while trying to find her husband. The moment when Ellie runs away from her alter to get into Peter’s waiting car has become one of the most classic Hollywood scenes of all time. Lauded as one of the greatest films ever made, the rom-com went on to inspire countless films of the genre and is the first of only three films to win all five major Academy Awards. Rent or buy on Apple TV.