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5 Films to Watch if You Liked 10 Things I Hate About You

Heath Ledger, left, and Julia Stiles in 10 Things I Hate About You

We’ve been there. You’ve just watched the masterpiece that was 10 Things I Hate About You and you’re looking for more films to watch that will fill that “Can’t Take My Eyes Off You”-shaped hole in your heart. But it’s hard to find great rom-coms, especially if you’re looking for great movies from the past. If you’ve already memorized every line of Clueless, Legally Blonde, Mean Girls, My Best Friend’s Wedding, Romeo + Juliet and the usual titles that show up when you’re looking for recommendations, it won’t be easy to find your next favorite watch. But we’d still like to help! We made a list of 5 films to watch if you liked 10 Things I Hate About You that also includes some new releases. You’ll find all the movies below in alphabetical order: enjoy!


1. Anyone But You (2024)

Will Gluck

Anyone But You (Sony Pictures Entertainment)

When it comes to new releases, it can’t get more recent than this. Anyone But You came out a few months ago, and it has already taken the world by storm thanks to the charm and charisma of its central leads, Glen Powell and Sydney Sweeney, and a script that channels the best rom-coms from the past. The first thing is has in common with 10 Things I Hate About You is Shakespeare: if your favorite Heath Ledger comedy was based on Shakespeare’s “The Taming of the Shrew,” Anyone But You takes inspiration from “Much Ado About Nothing” instead.

A young woman named Bea (Sweeney) runs into a stranger named Ben (Powell) at a cafe. The two are drawn to one another, spend a night together, and… Due to what happens the following morning, they immediately start hating each other. Little do they know that Bea’s sister Halle (Hadley Robinson), who’s about to get married in Australia, has invited them both to the wedding. Anyone But You doesn’t renew the rom-com genre, but it has plenty of personality and there’s even an irresistible musical number involving a very popular pop song, just like in 10 Things I Hate About You. Give it a try: you won’t be disappointed!


2. A Cinderella Story (2004)

Mark Rosman

A Cinderella Story
A Cinderella Story (Warner Bros. Pictures)

Here’s a film that came out many years ago but that a lot of people tend to overlook. A Cinderella Story, inspired not by Shakespeare but by the titular fairytale, is about a Californian high school student named Samantha Montgomery (Hilary Duff). Sam’s “wicked stepmother” Fiona (A pre-The White Lotus Jennifer Coolidge) forces her to wash dishes and mop floors at her diner whenever she’s not studying: any research paper service can tell you that it’s not an enjoyable way to spend your high school years.

One day, after an incident involving a phone, Sam starts anonymously texting a boy who turns out to be her Prince Charming. But things get complicated for Sam, who finds out that her date is Austin Ames (Chad Michael Murray), the most popular boy at school, right after they agree to meet for the first time, at the school dance. Will she be able to look the part, despite everyone working against her?

A Cinderella Story is a lighthearted watch that follows predictable beats, and yet it is guaranteed to put a smile on your face. Not only that, but if need of more “Cinderella stories” after the credits roll, you’ll find not one but five sequels to check out! Prepare to suddenly remember great 90s songs that you had completely forgotten about!


3. Easy A (2010)

Will Gluck

Easy A (Sony Pictures Entertainment)

This list features not one, but two films from director Will Gluck! More than ten years before he made Anyone But You, the filmmaker directed this all-time classic starring Emma Stone, also based on a book. That book is Nathaniel Hawthorne’s “The Scarlet Letter,” which the film’s protagonist, high school student Olive (Stone), is currently studying in her class. Olive is not as popular as her best friend Marianne (Amanda Bynes), and when the latter asks her for the juicy details of how she spent her weekend, Olive makes up a lie about losing her virginity. But her plan to look “cool” backfires when someone overhears her and she suddenly gains a reputation for something she didn’t even do.

If you liked 10 Things I Hate About You, you should definitely watch Easy A. Though it’s not packed with twists, it a very funny movie with a standout performance from a young Emma Stone. Penn Badgley, Lisa Kudrow, Cam Gigandet, and Malcolm McDowell are also in the cast.


4. Happiest Season (2020)

Clea DuVall

Happiest Season review: Queer Christmas classic – Loud And Clear
Film Review: Happiest Season (Hulu) is a riotous recontextualization of Christmas comedy clichés and conventions.
loudandclearreviews.com

Is it too soon to start feeling festive? Regardless of what time of the year it is, you’ll find plenty to love in recent gem Happiest Season. At the center of it all are couple Abby (Kristen Stewart) and Harper (Mackenzie Davis), who have been in a very happy relationship for a while. But Harper hasn’t come out to her parents yet – something that Abby only finds out right before the two leave for Harper’s parents’ house, where they’re going to spend the holidays. Harper asks her to pretend to be just friends, and initially, it all seems to work. Needless to say, things don’t go as planned.

We’ve seen plenty of films with similar premises, yet Happiest Season will speak to you on a whole different level. Its big, all-star cast – including, among others, Alison Brie, Aubrey Plaza, Mary Holland, and Dan Levy – is part of the reason why the film works as well as it does, but the real star, here, is the screenplay (Clea DuVall and Mary Holland). If you liked 10 Things I Hate About You, what you’ll enjoy, here, are the dynamics between the characters and the chaos that ensues once Harper’s lie spins out of proportion.


5. To All the Boys I’ve Loved Before (2018)

Susan Johnson

To All The Boys I've Loved Before
To All The Boys I’ve Loved Before (Netflix)

If 10 Things I Hate About You begins with someone who declares they’re not interested in love, Netflix’s To All The Boys I’ve Loved Before is the exact opposite. The film’s protagonist, teenager Lara Jean (Lana Condor), has had many, many crushes in her life, despite her being so young. What does she do to get over them? She writes them all letters, which she never posts. Except that, one day, her little sister finds all the letters in her closet and decides to deliver them all, which means that every single person Lara Jean has ever liked is now aware of it.

Despite them being two completely different kinds of stories, 10 Things I Hate About You and To All The Boys I’ve Loved Before have quite a lot in common. They both take place in high school, they both revolve around a love story, and they’re both incredibly cute movies that you could keep watching for hours. But what To All The Boys also has are two sequels, which gives you even more films to watch!



The 5 movies listed above are all great choices of films to watch if you liked 10 Things I Hate About You! And if you still need more recommendations, why not try to catch up with Heath Ledger and Julia Styles’ filmographies? A Knight’s Tale and Save the Last Dance will both make you nostalgic in the best possible way! Happy watching!

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