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10 Romantic comedies about love/hate relationships

BY Anna Walker

2nd Jan 2023 Film & TV

10 Romantic comedies about love/hate relationships

Nothing keeps romcom enthusiasts glued to their seats more than a will they/won't they love/hate relationship. Here are 10 of the best. 

10. Cher and Josh - Clueless

Image via Clueless

The world of Jane Austen’s Emma is transported from Highbury to Beverly Hills in this unusually self-aware teen adaptation.

Mall sprees, lavish pool parties and hot new cars; ditzy teen Cher Horowitz has a “way normal life for a teenage girl”. Normally such unreliable narration would turn the audience against a character—especially one so concerned with the material things in life. But this high-schooler is different.

Cher wants nothing more than to build up her peers and care for her father, and nothing annoys her more than her do-gooder former step-brother Josh.

As they bond over Cher’s father’s lawsuit, Josh begins to see her softer side, and by the end of the film the pair can’t help but fall in love. Bless.

Our angsty teenage years are a crucial part of growing up, and Josh and Cher learn from their differences to help each other become better people. What better outcome for a love/hate relationship than that?


9. Tom and Summer - 500 Days of Summer

From a love/hate relationship that helps a couple grow to one that pulls them apart.

“This is a story of boy meets girl. But you should know up front. This is not a love story.”

So begins the tale of 500 days in the love life of greeting-card-writer Tom Hansen who meets, loves and grows to hate Summer Finn.

The indie film cleverly uses a central couple who seem perfectly matched to unravel the clichés of the romcom genre. Despite being soul-mates on the surface, along with Tom we’re soon taught that;

“Just because someone loves the same bizarro crap as you, doesn’t make them your soulmate.”


8.  Phil and Rita - Groundhog Day

Groundhog Day
Image via Groundhog Day

Anti-social weatherman Phil Collins (Bill Murray) is narcissistic, pessimistic, chauvinistic and a nightmare to work with. 

He makes no secret of his apathy when he is sent with his exasperated producer Rita (Andie MacDowell) to cover the annual Pittsburgh Groundhog Day.

When he awakes the morning after, he quickly discovers that he has been confined to a loop where he seems doomed to relive February 2nd for eternity—even suicide won’t free him.

Eventually, Phil learns to use the loop to become a better man—becoming proficient at piano and ice sculpture and even saving the lives of the townspeople—and so wins the affections of Rita.

This surprisingly high concept romantic comedy is estimated to span 33 years and 350 days in total; that’s one seriously long-term relationship.


7. Kat and Patrick - 10 Things I Hate About You

This feisty adaptation of Shakespeare’s The Taming of the Shrew isn’t your average teen rom-com fare.

The bard’s play is given an assuredly modern update. Film critic Guy Lodge called the picture notable for “tempering the misogyny of the source by giving its haughty adolescent Kat (Julia Stiles) more psychologically nuanced reasons for her romantic reticence.”

Ill-tempered Kat has truly met her match in bad-boy Patrick (Heath Ledger), who soon finds himself at the mercy of her sharp tongue.

The two bite each other’s heads of for most of the film until the final emotional scene where Kat lists all the reasons she hates Patrick only to admit, of course, that she doesn’t hate him at all.

Relationships don’t come much more love/hate than this.


6. Bridget and Mark - Bridget Jones’s Diary

Bridget Jones

Based on Jane Austen’s ultimate story of hate turned to love, Pride and Prejudice, Bridget Jones’s Diary stars Colin Firth and Renee Zellweger as two thoroughly modern singletons, bound together by a mutual distaste.

When Firth’s Mark Darcy first sees Bridget at a Christmas party, he bemoans; “I do not need a blind date. Particularly not with some verbally incontinent spinster who drinks like a fish, smokes like a chimney and dresses like her mother.” Ouch.

Eventually, after one seriously misinformed bunny costume, several awkward dinner parties and an unfortunate incident with a fireman’s pole, the pair finally begin to see each other’s good side as Mark declares; “I like you very much. Just as you are.”


5. Jan and Brad - Pillow Talk

Pillow Talk
Image via Pillow Talk

The first of three films to showcase the sizzling screen chemistry of Doris Day and Rock Hudson, Pillow Talk is jam-packed with sexual tension and flirtatious bickering.  

Confident interior designer Jan and playboy composer Brad have never met but are constantly at loggerheads over their shared party line.

After spying Jan dancing and feeling instantly attracted to her, Brad soon woos her with an alter ego, Texan Rex. Despite his hijinks, he can’t help but fall in love with her.

The original trailer for Pillow Talk dubbed it “the most sparkling sexcapade that ever winked at convection”.

Talking about the film in his autobiography, Hudson recalled the sparky chemistry he shared with Day. “Doris and I couldn’t look at each other. You know that sweet agony of laughing when you’re not supposed to? That’s what we had.”


4. Walter and Hildy - His Girl Friday

When hotshot newspaper editor Walter Burns learns that his ex-wife, and star reporter, is set to marry a dull insurance salesman, he decides to do everything in his power to win her back.

This screwball comedy is full of quick-fire insults and features some force-of-nature squabbling from romantic leads Cary Grant and Rosalind Russell.


3. Kathleen and Joe - You’ve Got Mail

You Got Mail
Image via You've Got Mail

The plot’s reliance on AOL, chat rooms and screen names (shopgirl You’ve Got Mail stands the test of time.

Kathleen Kelly (Meg Ryan) runs quaint independent bookstore The Shop Around the Corner. Unbeknownst to her, her online love NY152—aka Joe Fox (Tom Hanks)—is heir to Fox Books, the giant corporate book chain opening its latest store just a few doors down.

As their online relationship intensifies, Kathleen and Joe become real life enemies, then real life friends, and finally real life lovers. The moment when Joe reveals himself as NY152 in a New York park is as iconic as Meg Ryan’s final words; “I wanted it to be you, so badly.”


2. Joel and Clementine - Eternal Sunshine of the Spotless Mind

Polar opposites Joel Barish (Jim Carrey) and Clementine Kruczynski (Kate Winslet) meet on a train ride and immediately feel a spark. Little do they know that they have met before.

In fact, they were lovers for over two years before a bitter break up saw them decide to erase each other from their memories.

As the recollections start to slip away, so does the hatred, until they’re locked in a desperate bid to escape the erasers and save their memories.

This love/hate relationship is surreal, fragmented and intensely romantic.


1. Harry and Sally - When Harry Met Sally

“Men and women can’t be friends because the sex part always gets in the way.”

From the second they first lay eyes on one another, Harry and Sally couldn’t be more different. Sally Allbright is buttoned-up, proper and very polite. Harry Burns is liberal, cheeky and always quick to poke fun.

The pair meet in 1977, when they carpool from Chicago to New York. They spend the journey shocked by their differences, and in total disagreement about the philosophies of sex and relationships. Their stubbornness might just be the one thing they have in common.

Harry and Sally start out as enemies, but as the years roll by—along with break ups, make ups, and several arguments—they become best friends, and eventually fall in love.

It would take a heart of stone to feel nothing when Harry confesses:

“I came here tonight because when you realise you want to spend the rest of your life with somebody, you want the rest of your life to start as soon as possible.”

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