35 Movies Like 10 Things I Hate About You That Have All the Teen Movie Tropes You Love

For another ’90s teen classic where a guy is way too pressed to get a girl who quite frankly enjoys her own company, there’s She’s All That. Popular jock Zack Siler (Freddie Prinze Jr.) has to turn outcast artist Laney Boggs (Rachael Leigh Cook) into prom queen material to win a bet and protect his reputation. For the record, because apparently, it needs to be said: Laney was beautiful with her glasses! While we we don’t exactly buy into the makeover trope that riddles teen movies of yesteryear, there’s still a lot to enjoy in this classic, like the stunning Gabrielle Union, who steals every scene she’s in.

Did you know that Clueless is an adaptation of Jane Austen’s novel, Emma? We love a good ol’ literary-classic-turned-iconic-teen-flick. If you’re, like, “totally buggin'” and have yet to see the movie, Clueless is about a rich, popular, and shallow Beverly Hills high schooler, Cher, who takes newcomer and tomboy Tai under her wing. Give it a watch and you’ll be adding “as if!” into your everyday vocabulary in no time. Though Clueless certainly has its issues, it still has more than enough lovable aspects. Case in point, the nostalgic ’90s outfit inspiration!

If you’re looking for another Shakespeare adaptation, look no further than Romeo + Juliet, starring ’90s teen heartthrob Leonardo DiCaprio and Claire Danes as the star-crossed lovers. The film updates the tragedy’s setting to a modern Verona Beach while keeping the bard’s original dialogue. From director Baz Luhrmann, also known for his film adaptations of The Great Gatsby and Moulin Rouge!, you can expect a dynamic, dazzlingly colourful, energy-filled re-imagination of a timeless classic.

Like 10 Things I Hate About You, Deliver Us From Eva is an adaptation of Shakespeare’s The Taming of the Shrew. But this time, Gabrielle Union is front and centre as Eva, a Type-A health inspector who rides hard for her sisters. Unfortunately, Eva’s sisters’ boyfriends and husbands can’t get what they want in their relationships on account of Eva’s constant interference and the fact that her sisters defer to her advice. So, the men conspire to pay player Ray Adams (LL Cool J) to woo Eva and distract her from her sisters’ love lives. The talented cast also includes Meagan Good and Essence Atkins.

Ah, the movie that made the internet fantasize about Noah Centineo spinning us around by the back pocket of our jeans. Based on Jenny Han’s novel, the Netflix film is about Lara Jean Covey, a hopeless romantic who gets into a bind when her sister mails her secret love letters to all of Lara Jean’s past crushes, including Peter Kavinsky (Centineo). When Lara Jean and Peter enter an agreement to pretend to date, they start to catch real feelings. If there’s one thing to be learned from 10 Things I Hate About You and To All The Boys, it’s that little sisters can either wreak havoc or do wonders for a big sister’s love life.

If you love 10 Things I Hate About You because you’re a Julia Stiles stan, then you have to watch Save the Last Dance. In the movie, Stiles is ballet dancer Sara, who moves to the south side of Chicago with her father after her mother dies. At her new school, she meets Derek (Sean Patrick Thomas), a talented hip-hop dancer who teaches her new moves and inspires her to chase her dreams. As Derek and Sara get close, their connection goes beyond the dance floor, and romance brews between the two. Together, they navigate the challenges that arise from having an interracial relationship in their inner-city high school.

As far as dramatic movie makeovers go, Princess Diaries has got to have one of the most memorable. The story of how Mia Thermopolis (Anne Hathaway) went from being a socially awkward teenager trying to make it through the throes of high school to being the princess of Genovia, a fictional small European kingdom, was formative for so many young viewers. Royalty aside, Mia stays true to herself just like headstrong, whip-smart Kat. And Julie Andrews, the epitome of elegance, lights up the screen and warms hearts as Mia’s grandmother, Queen Clarisse Renaldi.

Patrick charmed Kat by serenading her during soccer practice with the song “Can’t Take My Eyes Off You,” and Joey Parker (Drew Seeley) in Another Cinderella Story took a similar route when he put the moves on Mary (Selena Gomez). Dance moves, that is. Though there are many, many modern renditions of Cinderella’s story, I’d go out on a limb to say the one starring Gomez as an aspiring dancer and Seeley as a famous pop star returning to high school is one of the best.

Based on Becky Albertalli’s novel, Simon vs. the Homo Sapiens Agenda, this flick is an uplifting, coming-of-age, coming-out story. When another student anonymously comes out online at his high-school, Simon (Nick Robinson) starts a lovey dovey email correspondence with him. The hidden identities are definitely giving Shakespeare-esque comedic and romantic entanglements. At the same time, Simon tries to find a way to come out to his family with the help of his supportive friends.

The Love, Simon cast is stacked, featuring Jennifer Garner and Josh Duhamel as Simon’s parents, Natasha Rothwell as a scene-stealing drama teacher, and Alexandra Shipp as one of Simon’s friends. Oh, and did I mention Love, Simon made history as the first film by a major Hollywood studio to focus on a gay teenage love story? More of this, please!

Will Smith has made movies in every genre under the sun – action, sci-fi, biopics, and tearjerker dramas. But as dating coach Alex Hitchens, aka Hitch, he brings his charisma and talent to the forefront. With its well-intentioned, though sketchy, undercover wingman-ship, Hitch‘s plot will definitely remind viewers of 10 Things I Hate About You. Hitch’s goal is to get his insecure client, Albert (Kevin James), the woman of his dreams, who just so happens to be majorly out of his league. At the same time, cynical tabloid reporter Sara Melas (Eva Mendes) starts to fall for Hitch’s charms. Unbeknownst to her, he’s the “date doctor” she’s been trying to expose.

Believe it or not, this teen comedy masterpiece is multihypenate Olivia Wilde’s first feature film as a director. In Booksmart, Kaitlyn Dever and Beanie Feldstein star as Amy and Molly, two overachievers who have spent their time in high school entirely focused on getting into their dream colleges. When they find out the classmates they look down on for spending their time partying also got into their dream schools, they embark on a wild night, one last stand, to make up for lost time.

Just like 10 Things I Hate About You delights viewers with its sprawling cast of soon-to-be stars, you’ll be pleasantly surprised with Booksmart‘s cast of familiar faces (including Wilde’s ex-boo Jason Sudeikis as school principal by day, Uber driver by night).

In the Netflix romantic comedy Set It Up, two overworked assistants, Harper Moore (Zoey Deutch) and Charlie Young (Glen Powell), come up with a plan to get their two bosses, Kirsten (Lucy Liu) and Rick (Taye Diggs), together in the hopes some love will soften them up. Because nothing gets your boss to be less demanding or more pleasant than some romance, right? Though Harper and Charlie try their best to keep their bosses together, things don’t go exactly according to plan.

For another women-led film (Karen McCullah and Kirsten Smith wrote 10 Things I Hate About You), watch Greta Gerwig’s Academy Award-winning coming of age drama Lady Bird. The film stars Saoirse Ronan as strong-willed and deeply opinionated teenager Christine in her senior year of high school. Over the course of the movie, Christine butts heads with her hardworking mother (Laurie Metcalf), joins the theatre program with her bestie (Beanie Feldstein), and learns tough lessons about love and sex. Beyond its sincere, authentic storytelling, Lady Bird is also one of the films that put wunderkind pretty-boy Timothée Chalamet on our radars. But we’ll definitely take Heath Ledger’s Patrick Verona over Chalamet’s Kyle any day.

If you’re unfamiliar with Cruel Intentions, it puts quite the twist on the teen movie genre. Cruel Intentions is similar to the story of 10 Things I Hate About You – someone deceptively tries to get someone else romantically involved and they catch real feelings – but very different in tone. Set in the world of New York City’s wealthy teenagers, diabolical Kathryn (Sarah Michelle Gellar) makes a bet with her stepbrother Sebastian, who treats women as conquests (big yikes!), so she can get revenge on an ex. He has to seduce Annette (Reese Witherspoon), a pawn in their twisted game and the headmaster’s daughter, determined to remain abstinent until marriage. If he fails, Kathryn gets his vintage Jag, but if he succeeds, Kathryn has to have sex with him. What follows is a spicy series of lies, deception, betrayal, and filthy rich prep-school teenagers with way too much time on their hands.

Fair warning: this movie is not to be taken seriously, at all. Not Another Teen Movie is a raunchy spoof of a composite of your favourite classic teen movies like She’s All That, Pretty in Pink, Bring It On, Cruel Intentions, and, yes, 10 Things I Hate About You. There’s even a parody of the iconic scene of Patrick serenading Kat on the bleachers. Chris Evan’s character, Jack Wyler, completely and hilariously botches a serenade to Janey Briggs (Chyler Leigh). Prepare yourself because this movie is coming for all the teen rom-com tropes and stereotypes.

Bend and snap, folks! In this cult classic, Elle Woods (Reese Witherspoon), decked out in her signature pink, goes to Harvard Law School, at first to win back her boyfriend, who has made the critical mistake of underestimating Elle’s intelligence and determination. Soon enough, Elle wises up, realises her boyfriend is a major jerk, and proves to everyone that they should stop judging a book by its cover, or a girl by her blonde hair. Similarly to how Kat is constantly misunderstood by her classmates, so is Elle Woods the moment she steps onto Harvard’s campus.

Amanda Bynes was ubiquitous in early 2000s teen comedies. What a Girl Wants takes her across the pond as American teenager Daphne who goes to England to meet her estranged father. Turns out, he’s an English lord who’s running for political office! As you can imagine, Daphne is in for a bit of culture shock, clashes with her father’s English family, and pressures to fit into the English aristocratic crowd. Along the way, she finds herself a cute British boy, too.

Who said you need a bae for romance? Sometimes your friends are all the love you need when a relationship has made a turn for the worst. Netflix comedy Someone Great flips the rom-com on its head as a breakup comedy instead. After Jenny’s (Gina Rodriguez) boyfriend of nine years dumps her, her girlfriends Blair (Brittany Snow) and Erin (Dewanda Wise) come to the rescue to take her out for their last big hurrah in New York City before she moves for her dream job. Get together with your besties to watch this heartwarming and hilarious flick.

It’s no secret that a little white lie can blow way out of proportion. In this adaption of the classic novel The Scarlet Letter, Emma Stone is a teenager who flips a scandalous rumour about her first time having sex into a financial and social opportunity – and it’s not what you think. Teen comedies are notorious for perpetuating sexist beliefs and ideas about women and virginity, but Easy A is an unexpectedly funny, empowering critique of society that reclaims women’s sexuality. In addition to Stone, the movie also has performances from Penn Badgley, Amanda Bynes, Stanley Tucci, and Lisa Kudrow.

Adapted from the classic Jane Austen novel, Pride and Prejudice is a romantic period drama about the Bennett family, their life of manners and customs in the English countryside, and their mother’s efforts to marry off all of her daughters. Keira Knightley is the leading lady as outspoken Elizabeth Bennett, who has a love-hate relationship with Mr. Darcy, a handsome upper-class gentleman who seems reserved and cold at first. Like Kat, Elizabeth is witty and won’t settle for less than she deserves in love and life. Full of romance, intrigue, and tension, Pride and Prejudice is a gorgeous movie to watch cosied up on a rainy day.

If the title didn’t give it all away, this movie tells the story of a socially awkward 13-year-old girl, Jenna, who magically skips 17 years into the future and turns into her 30-year-old self overnight when she wishes she was a grownup. The adultified Jenna is played by none other than Jennifer Garner, who perfectly embodies the role. Unsurprisingly, Jenna learns real quick that adulting is not worth the hype. On the bright side, she finds her childhood best friend, Matty (Mark Ruffalo), as an adult, and what they find together is a little more than their childhood friendship.

This Netflix coming-of-age dramedy is one of many modern stories that riffs on the play Cyrano de Bergerac. To put it simply, it’s essentially a story where one person speaks through another person to woo a love interest. In The Half of It, football player Paul Musky pays Ellie Chu to write love letters to his crush, Aster Flores. Ellie can help her father pay the bills and Paul gets the girl, or so you think. In the process, Ellie actually befriends Paul and falls for Aster. Meanwhile, thinking Paul’s words are his own, Aster’s actually catching feelings for Ellie. Now, that’s a love triangle!

In 2022, this is no longer a hot take, but can we all agree the East Compton Clovers are way better than the Toros? They deserved their win in the final competition. Bring It On is a teen cheerleading competition film, starring Kirsten Dunst and the incomparable Gabrielle Union. Though it may seem somewhat superficial on the surface, this iconic comedy flick with its flips, cheers, and choreo is actually pretty deep in hindsight. It’s not just about overcoming adversity and winning competitions. Whether intended or not, it’s also a commentary on racial disparities, stereotypes, and cultural appropriation.

Another coming-of-age film, The Edge of Seventeen is about how school junior Nadine’s (Hailee Steinfeld) world gets turned upside down when her all-star brother starts dating her best friend. All of a sudden, Nadine feels alone in the world, with a mother who doesn’t understand her, her seemingly perfect brother, and a bestie who’s making new friends. With the guidance of her teacher Mr. Bruner (Woody Harrelson), who delivers his advice with a side of sarcasm and dark humour to match Nadine’s drama and angst, Nadine gets through the ups and downs of an awkward adolescence and the challenges of high school.

Written by John Hughes, known for his ’80s teen classics,Pretty in Pink focuses on an outcast, Andie (Molly Ringwald), a suburban Chicago teen who just doesn’t seem to fit in. In a cliquey school where everyone is obsessed with popularity and status, Andie isn’t one of the cool kids, much like Kat in 10 Things I Hate About You. Things seem too good to be true when rich, preppy kid Blane asks Andie out, but it’s not all sunshine and rainbows. Bonus: Andie and her best friend Duckie’s ’80s fits – the layering, the shoulder pads, the long pearl necklaces, the hats – are simply iconic.

The Perfect Date is about a high schooler who works at a sandwich shop who has the (maybe not so bright) idea to loan himself out to girls as the perfect date in the hopes that he can save up some money to finance his college dreams. In this Netflix comedy, after Brooks (Noah Centineo) pretends to be his classmate’s wealthy cousin’s boyfriend, he realises he has a knack for such deception and launches an app selling himself as the perfect plus-one. With all that lying and pretending to be someone he’s not, Brooks learns a much-needed lesson.

Based on the novel of the same name by Nicholas Sparks, Mandy Moore and Shane West are two North Carolina teenagers who seem like the last possible people who could fall in love. Bad boy Landon Carter gets to know the minister’s daughter Jamie after he’s forced to help with the school play as a punishment for one of his pranks gone wrong. No spoilers, but this romantic drama will bring you to tears with the insurmountable obstacles it throws as the young couple. Be warned: this movie might make you want to say to everyone, “You have to promise not to fall in love with me.”

Shout-out to Ryan Gosling’s abs, and Ryan Gosling’s abs only. If there’s one thing to be said about The Notebook, it’s that it’s quite steamy. Spanning across a few decades, The Notebook is an epic love story about Noah (Gosling), a boy from the wrong side of the tracks who falls in love with rich girl Allie (Rachel McAdams). Though they are desperately in love, a war, disapproving parents, and an engagement keep them apart. But, Noah and Allie find their way back to each other somehow and rekindle their love affair.

If 10 Things I Hate About You left you wanting to see more Heath Ledger, watch A Knight’s Tale next. In it, Ledger plays a dashing knight trying to win the affections of a fair maiden in medieval Europe. And the jousting tournament is the way to do it. This movie is definitely giving medieval fairy tale vibes with its court dancing, knight’s tournaments, castles, and candlelit kisses. Plus, Ledger’s wink and smirk are enough to make us swoon any day.

Way before Patrick Dempsey was known affectionately as McDreamy, he was nerdy high schooler Ronald Miller in teen classic Can’t Buy Me Love. In the movie, he comes to cheerleader Cindy Mancini’s rescue when she accidentally destroys her mother’s designer clothes. In exchange, Cindy pretends to be his girlfriend for a whole month to increase his popularity index on campus. As time passes, though, Cindy’s affection for Ronald grows to be genuine, while Ronald soon realises popularity might not be worth the hype.

Starring Nick Cannon and Christina Milian, Love Don’t Cost a Thing is a 21st-century remake of Can’t Buy Me Love. And, yes, it is named after a JLo song. The movie is about science nerd Alvin, who excels at engineering but leaves much to be desired in the dating department. When popular-girl Paris Morgan walks into the auto shop Alvin works at to get her mom’s car fixed, he does so on one condition: he’ll do it in exchange for two weeks of dating. Alvin finally has an in with the cool kids on campus, but at what cost?

Even though most boomboxes have been replaced by tiny bluetooth speakers, there are few ’80s movie images more iconic than John Cusack holding his boombox overhead. In this charming, critically acclaimed romantic drama about first love, Cusack plays optimist Lloyd who’s determined to win over his seemingly unattainable crush, Diane. Surprisingly, she’s just as into him, but it’ll take Diane and Lloyd a whole lot of effort to keep their love strong with Diane’s disapproving father in the picture.

Never Been Kissed came out the same year as 10 Things I Hate About You – 1999 was a solid year for the romantic comedy. But this one’s got a bit of twist. Drew Barrymore is a baby-faced reporter for the Chicago Sun Times newspaper who goes undercover as a high school junior to research teenage culture. She infiltrates a circle of the most popular kids on campus with the help of her brother. But she also falls for her attractive English teacher. As you can imagine, there is some major confusion ahead. Just see for yourself!

You may know Melissa Joan Hart from the OG Sabrina the Teenage Witch, but there’s no spells being cast in this rom-com staple. In the movie, Nicole (Hart) and Chase (Adrian Grenier) live right next door to each other, but they might as well live on different planets. In the interest of making their own love interests jealous, they pretend to date each other. We know how this tune goes. Turns out, Nicole and Chase might be more into each other than they previously could’ve imagined.

In 10 Things I Hate About You, one of the things that makes Kat such a cool, contemporary, feminist character is her unwillingness to compromise on her dream of going to college, boyfriend or not. If you ever wondered what it might be like to see her out of Padua and past high school, watch Down to You. It’s love at first sight for college students Imogen (Julia Stiles) and Al (Freddie Prinze Jr.). But outside forces threaten to get in the way of their love reaching its full potential.