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Top 5 Best Rom-Coms of All Time

Updated: Nov 16, 2023

By: Brooklynn Doren

Even though clichés are tired and overused everyone still loves them. I’ll admit I have dreamt of falling in love in a foreign country or having someone romantically chase me through the airport only to confess their undying love.

I love sunsets, long walks on the beach, handwritten letters, and kissing in the rain.

Romantic comedies are filled with all these classic cliches and endings. They are perfect to binge-watch on a Sunday afternoon or when you want to curl up in a ball on a sad lonely night.

The genre’s purpose is to bring joy to its viewers and rightfully so. However, this makes rating rom-coms extremely difficult. Take it from Vogue, “there is no ‘best’ romantic comedy. Something is funny when someone laughs or romantic when their heart swells, for better or for worse, and we have no right to say why one of these should top another.”

With that being said, I had a very hard time narrowing down this list, but regardless here are my top five favorite romantic comedies.

1. How to Lose a Guy in 10 Days

How To Lose a Guy in 10 Days is a cynical masterpiece and some may even call it an “anti-rom-com.” It uses every trope from each iconic rom-com.

The characters’ meeting is forced and both are looking for complete opposite things.

Benjamin Berry (Matthew McConaughey), a giant hotshot and advertising executive, places a bet to win a big campaign to prove he can make a women fall in love with him in 10 days. While Andie Anderson (Kate Hudson) the “How To” girl for Composure magazine is hoping to write an article about “How to Lose a Guy in 10 Days.”

The two meet at a bar and start to pursue one another. The problem they run into is out of the ordinary and craziness ensures. After a long 10 days and a surprising love story, the two feel as if they have a genuine connection. Andie tells her boss she cannot publish the article but that is until she becomes aware of the bet.

Ben, on the other hand, figures out Andie’s intentions and the two split ways. Yet, the journey doesn’t end there. Andie ultimately publishes the article and states “she lost the one person she ever fell for.” Ben reads the article and does the famous “running after her” move.

In the end, they live happily ever after.

2. 10 Things I Hate About You

When you think of rom-coms, you think of 10 Things I Hate About You. It’s a new take on an old story, the Shaksperian comedy “Taming of the Shrew.”

Yet, everything about the movie is so ‘90s, and what millennial doesn’t want to live in the ’90s?

Not only that, but the movie contains the most iconic scene of all time — the bleacher serenade! Patrick Verona (Heath Ledger) charms the audience as he breaks out in song and dance to “Can’t Take My Eyes Off You.”

Luckily Patrick doesn’t just win the hearts of the audience but he gets his girl, Kat Stratford (Julia Stiles) who’s cold, intelligent and always unapologetically herself. Teenage girls everywhere are in dire need of a role model like Kat and 10 Things I Hate About You gives us that.

3. To All The Boys I’ve Loved Before

Every teenage girl has been in Lara Jean’s position. We fantasize more about falling in love than actually being in it.

Lara Jean (Lana Condor) feels like she plays sidekick for most of her life, but everything changes with a series of letters. When the letters she wrote to all the boys she has ever “fallen in love” with suddenly go missing, everything becomes chaotic.

When Peter Kavinsky (Noah Centineo), the hottest boy in school, gets Lara’s letter, he proposes they fake date in order to make his ex-girlfriend jealous and make the other letter recipients believe she’s moved on. The two quickly realize that their fake relationship is heading in a different direction than they originally intended.

While both succeeded with their plans, they ultimately don’t care in the end. They fell in love with each other, but for real this time.

4. Clueless

Have you ever been “butt crazy” in love with someone? Do you know someone who’s a “snob and a half?” Are you “totally buggin?”

If you’ve used any of these slang terms, you are quoting Clueless and you probably don’t even know it.

While the world still pulls inspiration from the classic movie, most people long for a love story like Josh and Cher’s.

Josh (Paul Rudd) is a major “loser” in the eyes of Cher (Alicia Silverstone), a “superficial space cadet.” In the beginning, she never had the intention of falling in love or even being friends with him.

They fight with each other, knit-pick everything the others does, and even wrestles. While the audience sees this romance bud before they even do, Cher and Josh eventually pick up on it.

When they finally end up together, they learn what loving someone really means; it helps you learn about your individuality and it saves you from yourself.

5. 27 Dresses

Jane Nichols (Katherine Heigl) believed she was a “born to be a bridesmaid.” Her role is that of a self-sacrificing protagonist whose kindness is hardly appreciated and most of the time is betrayed.

Jane spent most of her life pining over her unappreciative boss George (Edward Burns), who instead falls in love with Jane’s sister, Tess (Malin Akerman). Despite this, she still agrees to plan their wedding.

During the process, she is constantly bugged by journalist Kevin Doyle (James Marsden), who slowly peaks Jane’s interest. Little does Jane know, she’s just Kevin’s ticket to a better job. This doesn’t stop Jane from fighting for Kevin though as she makes one insanely bold move along the way. And this is when their love story truly begins again.

27 Dresses received a lot of negative feedback though it did not deserve it. The movie gave the audience a coming-of-age love story with excellent character development.

So whether you’re craving your own “happily ever after” or just a movie to fill the void, the list above is a great way to get started.


What’s your favorite rom-com? Let us know on Instagram and Twitter!

Reach the writer on Instagram


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