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Tom Hanks and Meg Ryan in You've Got Mail
Photo via Warner Bros. Pictures

The 10 best enemies to lovers movies, ranked

The '90s and aughts were a golden time for romantic comedies.

If there’s one thing we love in movies, it’s when two distinctly different and adversarial people end up falling each other. This is what’s colloquially known as an “enemies-to-lovers” story. Typically, an enemies-to-lovers, which is usually a romantic comedy, features two people who don’t like each other, are forced to spend time together and eventually fall in love.

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The characters often grow emotionally and discover things about themselves they didn’t know over the course of the movie. The movies work because we get complete arcs as the main characters go from “I can’t stand you” to “I can’t stand to be without you.”

The premises are wildly different but they all pretty much have the same thing in common: hoo boy, do these two hate each other. In fact, the more they hate each other the better it feels when they finally do get together. Movies like this are a form of escapism, and what better way to escape than watch two people hilariously hate only to soften up eventually. Of course, a lot of this depends on the skill of the actor, although you could arguably say that about any movie, or shoot, any story regardless of drama.

The best enemies-to-lovers movies have two leads who have incredible chemistry, a lot of flirty banter and at the end everything gets wrapped up in a climactic moment where they finally get to be together. Some can be unbearable cheesy and dumb; others are practically classics. Let’s take a look at the 10 best enemies-to-lovers movies.

Pride and Prejudice

Based on the classic novel of the same name from legendary writer Jane Austen, Pride and Prejudice is the eventual love story of Elizabeth Bennet and the proud but emotional Mr. Darcy. Despite him being filthy rich, Elizabeth reads Darcy’s reserved demeanor as arrogance and forms a negative opinion of him. After a while of hating each other they soften up, but Darcy’s pride and Elizabeth’s prejudices get in the way.

How to Lose a Guy in 10 Days

This delightful Kate Hudson and Matthew McConaughey movie was released in 2003 and hangs on a fairly simple premise: Hudson plays journalist Andie Anderson, who has a wacky idea for an article — write about how to turn a man off by making classic dating mistakes. Unbeknownst to her, Benjamin Barry (McConaughey) made a different bet with his friends: that he could make a woman fall in love with him in 10 days. Once they find out the truth, they both have to decide if the other one is worth it. It’s actually great.

Sweet Home Alabama

Named after a Nickelback song of the same name (just kidding, it’s Lynyrd Skynyrd — just seeing if you’re paying attention), Sweet Home Alabama came out in 2002. Were the aughts the golden age of enemies-to-lover movies? Indeed they were. This one stars Reese Witherspoon, Josh Lucas, and Patrick Dempsey. Witherspoon plays successful New York fashion designer Melanie Carmichael who never got divorced from childhood sweetheart Jake (Josh Lucas). She thinks she wants to marry rich guy Patrick Dempsey but Jake won’t sign the divorce papers and that makes her really mad. Eventually they reconcile but it’s a tough road to get there.

The Proposal

This 2009 film starring Sandra Bullock and Ryan Reynolds tells the story if Margaret Tate, a wealthy book editor who’s about to get deported to Canada. In a panic, she decides on a plan. She’ll marry her assistant Andrew (Reynolds) by blackmailing him. Andrew goes along with the plan on one condition: he gets a promotion and his book gets published. The two are constantly at each other’s throats but the more time they spend together, the more they grow to like each other. Eventually, they have to decide whether to go through with the marriage or not.

Clueless

https://www.youtube.com/watch?v=9Um1SvJvDLY&pp=ygUQY2x1ZWxlc3MgdHJhaWxlcg%3D%3D

Clueless is a 1995 classic starring Alicia Silverstone as Cher, a popular high school girl. Cher is a wealthy girl who loves to help out her friends and crushes on Christian Stovitz. Unfortunately, he doesn’t return her affection and she gets crushed herself. However, her antagonistic relationship with her former stepbrother Josh Lucas (Paul Rudd, not the actor Josh Lucas from Sweet Home Alabama) becomes an unexpected romance. It’s a classic for a reason!

27 Dresses

This 2008 comedy starred Katherine Heigl as Jane Nichols and James Marsden as Kevin Doyle. Jane has been a bridesmaid 27 times and is basically known as a selfless person. However, she has a secret crush on her boss. This one has a bit of a twist on the enemies-to-friends plot device because Kevin and Jane just end up being friends, but things end up working out fine for her in the end.

Beauty and the Beast

Who doesn’t get along less than Belle and the Beast? In the beginning, anyway. This 2017 remake starred Emma Watson as Belle, a bookworm who loves adventure and hates her suitor Gaston. After her father Maurice gets imprisoned by the Beast, Belle makes a deal with the Beast to trade places with her father. Belle eventually goes from hating the Beast to falling in love with him, and once she professes her love for him he returns to his human form.

You’ve Got Mail

It’s weird to think of a time when email was just a new thing, but the You’ve Got Mail voice snippet was so ubiquitous in 1998 that you had to be a hermit not to know what it was in reference to. This is one of the quintessential enemies-to-lovers movies, as Joe Fox and Kathleen Kelly are two hated business rivals who fall in love anonymously through email.

One Fine Day

This 1996 film starring George Clooney and Michelle Pfeiffer in their primes tells the tale of two single parents named Jack and Melanie, who are thrust together by fate in New York City. They initially can’t stand each other but as they keep bumping into each other throughout the day their feelings change. At the end of the day, they decide to go for it and the script does a great job (not to mention the actors) to make it all seem believable.

A Walk to Remember

This heartbreaking 2002 film is based on a Nicholas Sparks novel of the same name. It’s the unlikely love story between popular high school jock Jamie Sullivan (Shane West) and Jamie Sullivan (Mandy Moore). They initially do not like each other (a classic enemies-to-lovers plot device) but over time they become friends and after that even more. However, Jamie has a terminal disease so that complicates everything, but at least they get to be in love for a while.


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Jon Silman
Jon Silman was hard-nosed newspaper reporter and now he is a soft-nosed freelance writer for WGTC.