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25 Movies Where Enemies Fall in Love

Through the misread signals, emotional murkiness, and mutual loathing, we know star-crossed characters unwittingly falling in love when we see them. But somehow, they never see it coming.
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Nothing says “love is blind” like falling in love with your nemesis. No matter how or when they finally see the light, these enemies-turned-lovers always have one key thing in common; they couldn’t see clearly at first. But while they’re busy harshly misjudging each other and ruling out romance the moment they meet, we all know what’s coming.

All of that “will they or won’t they” tension amidst their ongoing warfare makes the fated moment they inevitably realize they’re meant to be oh so bittersweet. This is especially true for the most impossible love stories of the bunch. Ready for an emotional rollercoaster? Here are our top 25 movies where enemies become lovers, starting with one of the most iconic “ah-ha!” moments in ’90s cinema.

Clueless

Binge Society/Paramount Pictures

Cher (Alicia Silverstone) and her ex-stepbrother don’t get along. Josh (Paul Rudd) thinks she’s “a superficial space cadet” and she thinks he’s a brown-nosing freeloader who should go “torture another family.” As their lives intermingle, their ex-sibling rivalry slowly transforms. They start to see the good in each other but refuse to admit it.

When Cher finally realizes she’s “butt crazy in love” with Josh, it throws her for a major loop. In this classic case of opposites attract, she’s not sure what to do next, but the reality is, Josh has been quietly pining for Cher for about half the movie. After her much-needed epiphany and a kiss on the stairs, they go from totally clueless to totally in love.

Silver Linings Playbook

Jennifer Lawrence and Bradley Cooper standing side by side and preparing to dance
The Weinstein Company/Mirage Enterprises

Tiffany (Jennifer Lawrence) and Pat (Bradley Cooper) know they have a lot in common, but neither of them considers that a good thing at first. Both struggling with their mental health, they agree to help each other out in different ways. Then they spend most of the movie in knock-down, drag-out disagreements.

Pat has lost his job and marriage. After spending time in a mental institution, he moves in with his parents and aims to rebuild his life and win back his wife. Tiffany offers to help him reconnect with his wife if he’ll be her partner in a dance contest. However, their agreement gets complicated when they start falling in love.

10 Things I Hate About You

10 Things I Hate About You dance scene
Touchstone Pictures | Buena Vista Pictures | YouTube

Very loosely based on Shakespeare’s The Taming of The Shrew, Cameron (Joseph Gordon-Levitt) can’t date Bianca (Larisa Oleynik) unless her older sister Kat (Julia Stiles) starts dating. Kat is anti-romance at the moment and her general abrasiveness scares teen boys. Cameron pays Patrick (Heath Ledger) to take Kat out and reluctantly, he agrees. It takes some convincing, but Kat says yes.

Equally misunderstood, they bond over not caring what others think but never expect to fall for each other. Once Kat lets her guard fully down, the truth comes out and heartbreak ensues. Luckily, the realness of their love proves greater than the fakeness of how their courtship began.

Moonstruck

Cher and Nicholas Cage in Moonstruck
MGM

Moonstruck introduced us to one of the most iconic love-hate relationships of all time. Starring Cher and Nicolas Cage, Loretta is engaged to Ronnie’s brother even though she admittedly doesn’t love him. Her mother says that’s a good thing because when you marry someone you love, “they drive you crazy.”

As it turns out, Ronnie is the one who drives her crazy in the best and worst of ways. They just can’t stay away from each other. One second, he’s carrying her to the bedroom. The next, they’re at each other’s throats. But their love is undeniable. In the end, they make things official, proving crazy, stupid, love always wins.

Star Wars: A New Hope

Carrie Fisher and Harrison Ford in forest
Lucasfilm/20th Century Studios/Walt Disney Productions/Bad Robot Productions/Ram Bergman Productions

To say Han Solo (Harrison Ford) and Princess Leia (Carrie Fisher) started off on the wrong foot in Star Wars: A New Hope would be an understatement. Their mutual animosity only increases, and she famously calls him a “stuck up, half-witted, scruffy-looking nerf herder.” Luckily, their relationship soon evolves for the better.

Thanks to these two, “I love you” being met with an “I know” is now one most memorable exchanges of sweet nothings in movie history. Since their first kiss, their love has endured many trials, to say the least. And while it ultimately seemed that maybe they weren’t quite right for each other, their love has never died.

Sweet Home Alabama

Reese Witherspoon and Josh Lucas up close and sitting side by side smiling
Touchstone Pictures/Pigeon Creek Films

Melanie (Reese Witherspoon) is about to marry the man of her dreams (Patrick Dempsey), but there’s one problem. She’s still married to her childhood sweetheart who still lives in her hometown. When she makes a trip to get Jake (Josh Lucas) to sign the divorce papers, their growing contempt for each other boils over.

Beneath all of those hard feelings, however, their lifelong love begins finding its way to the surface. Melanie soon realizes she left way more in Alabama than her past. She calls off the wedding at the altar, telling her amazingly understanding fiancee “I gave my heart away a long time ago.”

A Walk to Remember

Mandy Moore and Shane West in cafeteria scene
Di Novi Pictures/Gaylord Films/Pandora Cinema

Landon (Shane West) is the most popular guy in school. Jamie (Mandy Moore) is a kind, studious girl who keeps to herself. They know who each other are by reputation, but don’t know each other at all. When Landon gets in trouble with the law, he’s forced to do extracurricular activities he deems uncool. Jamie happens to be a part of all of them, and they form an unlikely friendship as she helps him out.

But first, Jamie makes him promise not to fall in love with her. He laughs it off and says “that’s not a problem.” Famous last words, Landon. At first, Landon prioritizes his rep and denies even knowing her. When he almost loses her, he realizes he loves her and soon prioritizes their relationship at all costs. Jamie eventually confesses she’s dying of leukemia. Before it all gets as sad as possible, their love brings them both to life.

How to Lose a Guy in 10 Days

Kate Hudson and Matthew McConaughey in restaurant scene
Paramount Pictures

In the beginning, Andy Anderson (Kate Hudson) and Benjamin Berry (Matthew McConaughey) view each other as nothing more than attractive targets. To get ahead in their careers, he’s tasked with making her fall in love with him and she has to make him “wish he was dead.” And even though Andy’s goal is to fully drive Ben away and out of his mind, true love gets in the way.

When the truth comes out about their business schemes, hurt feelings give way to hatred. They both have been dehumanized. She feels like a meaningless bet and he feels like a guinea pig who has been tortured for one of her columns. For a moment, they do lose each other, but only for long enough to realize they never want to lose each other again.

Pride & Prejudice

Elizabeth Bennett and Mr. Darcy start to dance in ballroom scene
Universal Pictures

Jane Austen’s Pride and Prejudice has had many movie and television adaptations since it was published in 1813. But the 2005 adaptation starring Keira Knightley and Matthew Macfadyen did the best job highlighting the ongoing conflict between Elizabeth Bennet and Fitzwilliam Darcy.

Elizabeth and Mr. Darcy clash immediately. Their pride, prejudice, and general stubbornness keep them from seeing beyond their differences. Still, their chemistry is undeniable. Mr. Darcy confesses his feelings first and says, “You have bewitched me, body and soul, and I love—I love—I love you. I never wish to be parted from you from this day on.”

Heartbreakers

Jason Lee kissing Jennifer Love Hewitt's head while she sleeps on bed in wedding dress
MGM/Winchester Films/Davis Entertainment

Heartbreakers is sorely underrated and so is the enemies-to-lovers dynamic within. Page (Jennifer Love Hewitt) and her mother (Sigourney Weaver) are con artists. Their marks are rich men that they trick into marriage, trick into cheating with either the mother or daughter, catch them, and then take them for everything they’re worth. But when Page meets Jack (Jason Leigh), those best-laid plans fall apart.

Page is nothing but nasty to Jack at first. But when she learns he owns the bar he works in, he becomes their new mark. Upon catching feelings, Page doesn’t want to go through with ruining his life. Her mother says she must follow through and that Jack will betray her on their wedding night like all the others. But he doesn’t. After a series of unfortunate misunderstandings and schemes, they find their way back to each other.

You’ve Got Mail

Tom Hanks and Meg Ryan sitting back to back while they unknowingly talk to each other on their computers in You've Got Mail
Warner Bros. Pictures

In You’ve Got Mail, Kathleen Kelly (Meg Ryan) runs a small and special bookshop. Joe Fox (Tom Hanks) has just opened a mega book emporium around the corner and he’s putting her out of business. Their business feud gradually gets worse. Kathleen aims to take Joe down and Joe calls her “a pill,” but there’s one problem.

These two are actually each other’s closest confidantes, but only online. When Joe finally figures out that his best friend online is actually his biggest foe in real life, he doesn’t know how to reconcile his feelings right away. But the plot twist allows him to see her in a new light, and he eventually wins her over.

Anchorman

fight scene in news room between Veronica and Ron
Apatow Productions/DreamWorks

Anchorman might be the silliest movie on this list, but that doesn’t make the “I hate you, I love you” story any less noteworthy. In the 70s, no one is bigger than Channel 4’s Ron Burgundy (Will Ferrell), except for maybe Veronica Corningstone (Christina Applegate) and her dreams of being a real anchor. When she joins the news team, times are changing in more ways than one, and not everybody is happy about it.

Throughout the movie, they have one heck of a power struggle. To make it in a man’s world, she does her best not to fall in love or be objectified. But when Ron serenades her with a saxophone, all bets are off. Still, his ego overshadows their bond. The idea that she might be better than him as an anchor turns their love toxic. They work it out in the end, but only after the most dramatic brawl between brooding lovers ever.

27 Dresses

Kathering Heigl and James Marsden bickering outside of a cab
20th Century Studios/SpyGlass Entertainment/Barber-Birnbaum/Fox 2000 Pictures

Jane (Katherine Heigl) is always a bridesmaid, never the bride. Kevin (James Marsden) is a reporter who takes an interest in her, first as a peculiar subject for an article and then more sincerely. While they both have their guard up going in, when they start to let it down, they quickly learn they’re not so different after all. In fact, these two are able to see each other in ways they both have spent way too long feeling unseen.

This only makes their attraction grow. But Jane has had her eye on someone else for years. Unfortunately, he’s about to marry her sister. Kevin tries to convince Jane that she can’t be a bridesmaid this time, having her best interest at heart. By the time they’ve evolved from adversaries to allies to something more, the “27 Dresses” article is published. Jane rightfully feels betrayed. But love, and James Marsden’s handsomeness, conquer all.

The Breakfast Club

kiss scene at the end of The Breakfast Club
Universal Pictures/A&M Records

The Breakfast Club forever proves that anything can happen in detention, including falling in love with someone who started out as your enemy. John Bender (Judd Nelson) is the rough and tough bad boy who is pretty much mean to everyone, but he’s meanest to the pretty, popular rich girl, Claire Standish (Molly Ringwald.)

Is this a case of picking on someone because you like them? Maybe so. But he definitely takes his inappropriate line of questioning and antagonizing way too far. And she’s not too fond of him in response. The anger they have for each other is intense. But what lies beneath is vulnerability. Claire is aware of what’s really going on and makes the first move because she knows he’ll never have the guts. Once fully disarmed, they kiss.

Leap Year

Amy Adams and Matthew Goode in bed next to each other
Universal Pictures/Spyglass Entertainment

Upon learning of an Irish tradition, Anna (Amy Adams) takes charge and decides to propose to her blasé boyfriend (Adam Scott) on a Leap Year. But she’ll have to get to him in Dublin first. Declan (Matthew Goode) is also going that way, so they agree to get there together.

Stuck side by side for the ride, they find themselves bickering all the time. They can’t wait to get away from each other but are pushed even closer when they must pretend to be a couple for lodging accommodations. After all the pushing and the pulling, they realize they were brought together for a fated reason.

What Happens in Vegas

Cameron Diaz and Ashton Kutcher in drunken Las Vegas wedding scene
Penn Station Entertainment/Regency Enterprises/Mosaic Media Group/21 Laps Entertainment

Jack (Ashton Kutcher) and Joy (Cameron Diaz) each fly to Vegas to forget their problems. They meet, have more fun than they’ve ever had, and wake up married. After spewing harsh digs and deciding to never speak again, Jack hits the jackpot, winning 3 million dollars as Joy is walking away. Cutting his celebration short, she reminds, “What’s mine is yours, baby. Remember?”

The court orders them to 6 months “hard marriage.” In constant battle, they both go out of their way to make the other one leave. After despising each other for their differences, they soon start to learn from each other too. That initial hatred eventually turns into love, and they realize maybe there was more to the drunken night they first spent together than a good time gone wrong.

Runaway Bride

Touchstone Pictures/Paramount Pictures Studios/Lakeshore Entertainment/Interscope Communications

Maggie Carpenter (Julia Roberts) is known around town as the Runaway Bride. She’s unavoidably lovable, always getting engaged to the wrong guy, and always getting cold feet at the wedding. One of the biggest problems is, she adjusts her interests to please each fiancee. Their hobbies become her hobbies, their favorite eggs are her favorite eggs. Ike Graham (Richard Gere) is writing a story about her. Needless to say, she’s not his biggest fan. And to be fair, he’s not looking at her through the most human lens.

The more time Ike spends with Maggie, the more he falls “under her spell” like all the others. Even though she’s already engaged, she falls in love with him too. After one surprisingly passionate kiss, their eyes are opened. This time, it’s real and right. But will Maggie run from the right guy too? The answer, at first, is yes. In the months they spend apart, Maggie spends time learning who she is and how she likes her eggs. Then she makes a B-line straight to Ike and re-proposes.

When Harry Met Sally

When Harry Met Sally famous diner scene
Columbia Pictures

When Harry Met Sally is one of the most iconic movies about enemies who become friends and then become lovers. When they first meet, Harry (Billy Crystal) tells Sally (Meg Ryan) men and women can never be friends because “the sex part always gets in the way.” Sally is disgusted by his outlook on life and Harry thinks she’s too uptight. When they meet again, they’re no closer to getting along. But after a few more breakups, a friendship forms and they get closer and closer.

When they finally cross the line, everything falls apart, as Harry first promised. But not forever. Harry races to a new year’s party and tells Sally that he loves her and says, “when you realize you want to spend the rest of your life with someone, you want the rest of your life to start as soon as possible.” Sally responds with, “You say things like that and you make it impossible for me to hate you.” And just like that, they live happily ever after, twelve years and three months later.

The Proposal

Sandra Bullock and Ryan Reynolds in argument walking around office together
Touchstone Pictures/Mandeville Films

Andrew (Ryan Reynolds) hates his demeaning boss Margaret (Sandra Bullock) and Margarate sees her assistant Andrew as her property. But when her visa is about to expire, she convinces Andrew to marry her so she won’t be deported back to Canada. Frankly, he isn’t really given a choice. Andrew also has plans to visit his family in Alaska, so Margaret comes along to make the ruse look real.

But once she meets his sweet, supportive family and learns more about Andrew’s character and background, she can’t go through with the sham marriage. At one point, she says, “it’s not easy to ruin someone’s life once you learn how wonderful they are.” Away from the office, he can also see what a tender person Margaret really is underneath the hard-as-nails facade. And inevitably, they end up together.

Romeo + Juliet

Romeo + Juliet 1996 meet scene
Bazmark Productions | 20th Century Fox | YouTube

In this tale as old as time, these two aren’t exactly enemies, but they’re supposed to be. When Romeo (Leonardo DiCaprio) and Juliet (Claire Danes) first lay eyes on each other, they don’t know who each other are, but their families have been at war for centuries. That news is a major bummer. Long-standing family feud aside, they’re in love immediately. And well, you know the rest.

The seething hatred between the Montagues and Capulets runs so deep that they both know there’s no way they’d ever win their parent’s approval. Still, these starcrossed lovers refuse to stay apart. Fighting for their love, they hatch a plan to fake their deaths and marry. But the curse on both their houses prevails in the most tragic of ways.

Warm Bodies

Warm Bodies
Summit Entertainment | Mandeville Films | YouTube

Loosely based on the OG Romeo and Juliet, the odds are even more stacked against these two. For starters, zombies and humans are inherently enemies. But in this paranormal zombie rom-com, love flips the script.

Julie (Teresa Palmer) recognizes that R (Nicholas Hoult) isn’t like other zombies pretty quickly. As love quietly brings him back to life, their forbidden bond keeps growing. Together, nothing is impossible. They soon change the fate of the lifeless world.

One Fine Day

Michelle Pfieffer looking at George Clooney in One Fine Day
20th Century Studios/Fox 2000 Pictures/Lynda Obst Productions

Starring Michelle Pfieffer and George Clooney, One Fine Day is another underrated classic about enemies becoming lovers. Late for big days at work, these single, working parents both miss the bus for their children’s field trip. Annoyed with the predicament, they have no choice but to put aside their differences for the day and help each other out.

Being forced to spend time together proves to be one of the best things that has ever happened to either of them. Per Rotten Tomatoes, “The formula remains evergreen — two attractive leads are thrown together by quirk; develop antipathies, even loathing; then, ultimately decide they have overreacted and are hopelessly in love.”

Bridget Jone’s Diary

Miramax/Universal Pictures/StudioCanal

The first time Bridget Jones (Renee Zelwegger) meets Mark Darcy (Colin Firth), it doesn’t go well at all. After overhearing his not-so-flattering first impression of her, she deems him her mortal enemy and loathes the very sight of him from that day forward. Naturally, it turns out to be a case of bad timing and misunderstandings.

Once again, the lead also has her eye on the wrong guy (Hugh Grant) for a little too long, creating a series of blind spots about what’s right in front of her. But when Mark Darcy finally works up the nerve to tell her he likes her “just the way she is,” a stunned Bridget soon sees that he’s the one she’s been looking for all along.

Dirty Dancing

the iconic dance lift at the end of Dirty Dancing
Vestron Pictures/Great American Films Limited Partnership

Johnny (Patrick Swayze) and Baby (Jennifer Grey) are a classic movie example of an enemies-to-lovers dynamic. At the start of Dirty Dancing, they hate each other as they don’t understand, or they don’t want to understand, their very different lives. Baby’s a wealthy daddy’s girl who’s had an easy-ish life and Johnny’s an employee known for his smooth moves and hangs with a tougher crowd.

When they’re forced to train together for a dance competition, their partnership quickly goes from bad to worse. Over time, as they truly learn to work together, care for each other, and develop something real, they start sweeping each other off their perfectly choreographed feet and have each others’ backs. Nobody puts Baby in the corner!

Mr. and Mrs. Smith

Brad Pitt and Angelina Jolie doing the tango
Regency Enterprises/20th Century Studios/Summit Entertainment/Regency Entertainment

John (Brad Pitt) and Jane (Angelina Jolie) are secret assassins working for adversarial agencies. When they fell in love and got married, they mutually “forgot” to disclose that detail. Like so many couples, their marriage stagnates, mostly because of all the things they aren’t saying to each other. But when they’re assigned to kill the same target, the truth comes out. They begin to wonder if they were both just each other’s cover all along.

Just when it seems their marriage couldn’t get any more complicated, they’re assigned to kill each other. But a very heated battle turns into a passionate rekindling of their very real love. While critics didn’t love the most modern version of Mr. and Mrs. Smith, most of them still agree that the chemistry between its leads was electric enough to carry it through.

Something’s Gotta Give

Diane Keaton and Jack Nicholson making pancakes in their pajamas at night in beach house
Warner Bros. Pictures/Columbia Pictures/Waverly Films

Harry Sanborn (Jack Nicholson) is an aging womanizer dating a much younger woman, Marin (Amanda Peet). When they take a trip to her family’s beach house, they find that her mother, dramatist Erica Barry (Diane Keaton), is already there. Making the best of the situation, nobody leaves right away, but they have a hard time hiding their general dislike of each other.

Erica doesn’t approve of the relationship and tells Harry she’s revolted by his sexist ways. But when Harry has a heart attack, a doctor (Keanu Reeves) prescribes bed rest and Erica is there for him. After she starts seeing the hot doc, Harry finds himself falling for her. Soon enough, they’re making pancakes in their PJ’s, opening up, and realizing they read each other all wrong. Now they just have to break up with everyone else.

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