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Rivalry Roundup: 8 of Cinema’s Greatest Enemies to Lovers

The enemies to lovers from the 90’s to now who make us believe in romance again.

Trill Mag/Laura Kelly

It is well known that the line between love and hate is thin and, in some cases, almost non-existent.  While in reality, this calls for serious self-reflection, on the silver screen, it is another story entirely. The enemies-to-lovers trope is beloved by many rom-com fanatics, capturing the searing passion of love that forces even the greatest of foes to bend to their desires.

From the gilded ballrooms of Bridgerton to the Irish fields in Leap Year, this article will dive into some of cinema’s greatest romantic rivals, looking at both classics and more recent releases and rating the elements that make their relationships so steamy and their love unforgettable.

8) Margaret Tate and Andrew Paxton – The Proposal (2009)

Andrew, a man with short brown hair and a grey-green jacket kisses Margaret, a woman with dark hair in a ponytail wearing grey. They are surrounded by people in a chalet room.
Credit: YouTube/AnimatedSquirrel

The Proposal follows Margaret Tate, an authoritative book editor facing deportation, who convinces her long-suffering assistant, Andrew Paxton to marry her in exchange for a promotion. However, keeping the charade up involves a weekend trip to Andrew’s hometown, a trip in which they gain a new understanding of each other and unexpected feelings.

Their hilarious bickering makes for one of the most entertaining couples on this list, and the tension simmering beneath their cutting banter charges every scene between them. Though certainly focusing on the comedy part of the rom-com, their easy familiarity and undeniable chemistry make the film heart-warming and light.

⭐⭐⭐⭐/5 stars for the iconic Girlboss and Malewife duo.

7) Ella and Charmont – Ella Enchanted (2004)

Ella, a woman with dark hair looks up at Charmont, a man with curly brown hair wearing a medieval tunic. They are both in the woods
Credit: YouTube/Miramax

If you like pretty boy princes paired with damsels who do the rescuing, then this is the couple for you. When Ella of Frell first meets widely adored Prince Charmont, his failure to impress her sparks interest, which is not returned, though Ella’s desire to break her curse of obedience binds their fates together.

Their journey through this fantasy landscape is punctuated with frequent spats. However, Charmont’s advocacy for Ella’s autonomy even in their less-than-friendly stages paves the way for a charming, modern fairytale romance, one where the princess can save her prince and herself.

⭐⭐⭐/5 stars for fairy tale romance deconstructions.

6) Patrick Verona and Kat Stratford – 10 Things I Hate About You (1999)

Patrick, a boy with long dark hair wearing a black suit kisses Kat, a girl in a purple dress wearing pearls and a flower in her blonde hair.
Credit: YouTube/Ironhorse1b

Perhaps the staple couple of the enemies-to-lovers trope, the romance of 10 Things I Hate About You starts less than ideally when charming outcast Patrick Verona is paid to date independent and argumentative Kat Stratford as part of a high school wager.

Though they certainly have their highs and lows, their clashing personalities hide fundamental similarities of experience that foster true connection. This connection breaks through both of their tough exteriors and allows for mutual growth, making them a perfect example of the enemies-to-lovers trope.

⭐⭐⭐⭐/5 stars for perfect high school banter.

-⭐ star for the “shut up” kiss trope.

5) Kate and Antony – Bridgerton (2022)

Antony Bridgerton, a man with brown hair wearing a suit looks into the distance as he helps Kate Sharma, a woman with dark hair and a green hat aim a gun.
Credit: YouTube/Still Watching Netflix

The “it” couple of the Netflix hit Bridgerton’s second season, Kate Sharma and Antony Bridgerton became one of the most widely praised enemies-to-lovers seen on screen. After Antony begins to court the younger Sharma sister Edwina due to family pressure to find a wife, he becomes caught in a battle of wits and indeed forbidden affections with Kate, who challenges him at every turn.

Moving from constant arguing to mutual respect and eventually to searing desire, their romance is one that is both thrilling and poignant, so much so that every viewer cannot help but root for their union. They are a perfect match, but one that faces every challenge in coming together.

⭐⭐⭐⭐⭐/5 for the infamous Bee Sting Scene alone.

4) Mia Thermopolis and Sir Nicholas – The Princess Diaries 2: Royal Engagement

Mia Thermopolis, a girl with dark brown hair wearing a blue dress looks longingly at Nicholas Deveraux, a man wearing a blue and white striped shirt.
Credit: YouTube/Rosy Neely

The childhood introduction to the enemies-to-lovers trope, this sequel to The Princess Diaries features the slow-burn romantic rivalry of Princess Mia Thermopolis and her competition for the throne of Genovia, Nicholas Deveraux.

Though Nicholas initially attempts to manipulate Mia at his uncle’s request, through their interactions they are forced to reckon with the mutual attraction beneath their supposed hatred. The slow development of their relationship makes for both a compelling and realistic romance, however, the fact of their being 4th cousins is difficult to ignore.

⭐⭐⭐/5 for Chris Pine and Anne Hathaway t o g e t h e r.

-⭐⭐ for questionable blood relations.

3) Anna Brady and Declan – Leap Year (2010)

Anna, a girl with red hair and Declan, a man with dark hair and wearing a blue striped shirt kiss passionately
Credit: 20th Century Fabios//Teazel Studios

When Anna Brady and Declan first meet, it is the opposite of a meet-cute. Anna Brady, a real estate agent, flies to Ireland to propose to her long-time boyfriend on Leap Day, following Irish tradition. However, one disaster follows another, leading Anna to hire Irish innkeeper Declan to take her to Dublin so that she can propose on time.

The premise behind their romance is creative, and their road trip is filled with mishaps and arguments, underlying which is an undeniable magnetism between the two. Though they seem to bring out the worst in each other, they cannot help coming back to the other.

⭐⭐⭐/5 stars for classic road trip bonding.

2) Alexander Claremont-Diaz and Prince Henry – Red, White and Royal Blue (2023)

Alex, a boy with dark hair, and Henry, a boy with blonde hair, sit facing each other in the woods.
Credit: Prime Video

Based on the critically acclaimed YA novel, Red, White and Royal Blue was one of the most anticipated romances of the year, precisely for the searing tension and quippy back and forth of its protagonists. Alex Claremont-Diaz, the son of the US president, finds himself caught in a fake friendship with Henry Stuart-Fox, 2nd Prince of England after a public argument leaves their respective reputations at risk.

Their petty bickering through forced proximity is endlessly amusing, and the chemistry between the two is undeniable, but most striking in the couple is the profound exploration of queer romantic experiences, which is both genuine and nuanced.

⭐⭐⭐⭐/5 stars for the love-interest-falls-first trope.

1) Stella and Will – Five Feet Apart (2019)

Stella, a woman wearing a pink dress, sits on the edge of a pool beside Will, a boy wearing a grey-blue shirt.
Credit: YouTube/Devesh Chettri

Another YA book adaptation but one far more underappreciated despite its excellent depiction of enemies to lovers. The movie follows two teen cystic fibrosis patients with very different outlooks on their illness. Stella, a type A optimist, finds herself perpetually at odds with Will, a rebellious realist who insists on getting under her skin. Yet perhaps, despite their differences, they may be able to bring out the best in each other.

The relationship between the two teenagers is particularly compelling and takes account of their differences so that their relationship develops slowly but naturally. Despite the emotional and physical distance between them, their care for one another is apparent and perhaps more moving than any on this list.

⭐⭐⭐⭐⭐/5 stars for love through insurmountable odds.

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