Romantic comedies are the emotional mixtapes of our lives. They're funny, messy, sometimes cringe, but always a little magical. 10 Things I Hate About You didn't just give us Heath Ledger's iconic bleacher serenade. It rewrote the rom-com playbook with sass, heart, and a killer '90s soundtrack that still holds up.
If you're craving movies that get how confusing and wild love really is but with a little humor, this list is your vibe. Capturing all the chaotic, sweet, and sometimes painfully awkward moments that make love stories totally binge-worthy, here are the 10 best rom-coms like 10 Things I Hate About You.
She's All That (1999)
She's All That is a classic makeover story that somehow never gets old because it's really more than a glow-up. Zack Siler is your typical high school golden boy who, after getting dumped for a reality TV star, bets he can turn any girl into a prom queen. Enter Laney Boggs, an artsy, introverted outsider who's basically allergic to high school popularity contests. What starts as a shallow bet turns into something way more real when Zack starts seeing Laney for who she really is. What makes this film special is its critique of high school superficiality and emphasis on the importance of actually getting to know someone. Like 10 Things I Hate About You, it blends sharp high school satire with romance, all while challenging social cliques and expectations.
The DUFF (2015)
The DUFF is basically a modern teenage battle cry for anyone who's ever felt like the "Designated Ugly Fat Friend," which, honestly, sounds way worse than it is. But it still stings because how can it not? The story follows Bianca, who loves her life with her two besties until she finds out she's been saddled with that awful label. Cue her mission to rewrite the social rules with a little help from Wesley, her charming neighbor and reluctant life coach. The cool part is how the movie tells us it's okay to reject labels and own your weirdness. Bianca's journey is funny, real, and gives major props to self-acceptance. This one echoes 10 Things I Hate About You in its message that being yourself (flaws and all) is way more powerful than fitting in.
Can't Hardly Wait (1998)
If you want a rom-com that's basically a high school party in movie form, Can't Hardly Wait is for you. The story is set during graduation night, and everyone's juggling crushes, secrets, and what-ifs. Preston Meyers has been crushing on Amanda Beckett forever and is finally ready to confess his true feelings to her. But as the night unfolds with wild twists and turns, you get this sprawling, chaotic snapshot of teenage life at its most awkward and hopeful. It perfectly nails that bittersweet feeling of endings and new beginnings and feels like the emotional hangover after your last high school party. Like 10 Things I Hate About You, it taps into the teenage whirlwind of big feelings, big risks, and that final push toward growing up.
Never Been Kissed (1999)
Never Been Kissed is a classic story of a good girl who secretly just wants someone to love her. While the concept might seem a little dated, it's still a cute story. Josie Geller is a 25-year-old copy editor who goes undercover as a high schooler for a story, which sounds way easier than it actually is. While she navigates mean girls, first crushes, and cafeteria politics all over again, Josie faces her own insecurities and gets a second shot at growing up. Barrymore's goofy charm makes this a heartfelt romp about learning to love yourself, even if it means reliving your most awkward years. It shares 10 Things I Hate About You's championing of misfits, and its message that love can show up when you least expect it
Drive Me Crazy (1999)
Drive Me Crazy follows Nicole Maris and Chase Hammond. Although they have been neighbors since they were kids, the pair couldn't be more different. They eventually pretend to date just to make their respective crushes jealous. But here's the twist: Spending all that time pretending eventually makes them realize they're actually into each other. The movie's got that mall-culture energy with boy-band tunes and messy hair, but underneath all that is a surprisingly sweet story about breaking down walls and learning to trust the unexpected. It also captures the same fake-dating-turned-real-love dynamic that 10 Things I Hate About You nailed so well.
He's Just Not That Into You (2009)
He's Just Not That Into You is the rom-com equivalent of relationship group therapy. Although the story follows several interconnected couples, the main protagonist is Gigi. Desperate to find love, she spends all her energy decoding mixed signals like they're ancient hieroglyphs with the help of a bar owner named Alex, which, if we're being totally honest, is a skill all of us need at some point. This film doesn't sugarcoat the messy, frustrating, and sometimes downright confusing world of modern dating. Instead, it's the perfect reminder that sometimes rejection doesn't make sense and that self-respect is the hottest thing you can wear. Though more adult in tone, it still reflects 10 Things I Hate About You's brutally honest take on love, especially when it's not going according to plan.
27 Dresses (2008)
27 Dresses follows Jane Nichols, who has been the ultimate bridesmaid for everyone she has ever known. But when her younger sister gets engaged to the guy she secretly loves, everything gets complicated, especially when Commitments columnist Kevin "Malcolm" Doyle is added to the mix. This movie dives deep into what it means to always put others first while forgetting to ask yourself what you want. Jane's bittersweet struggle with unrequited love mixed with the chaos of wedding planning reminds us that sometimes you've got to stop playing the supporting role in your own life. Its mix of self-discovery and snark will totally speak to fans of 10 Things I Hate About You's edgy vibe.
Clueless (1995)
Cher Horowitz (Alicia Silverstone) is the OG queen of teen rom-coms. She's rich, stylish, and totally clueless about her own heart while expertly meddling in everyone else's. If that sounds slightly familiar, it's because Clueless is a clever, hilarious modern-day spin on Jane Austen's Emma. This movie is equal parts fashion fantasy and surprisingly sharp social commentary. It's bubbly and fun, but underneath the iconic catchphrases and plaid skirts is a story about figuring out who you really are when the lip gloss fades. Much like 10 Things I Hate About You, Clueless is a smart literary update dressed in teen glam, with a heroine who learns that love and life aren't always what you expect.
How to Lose a Guy in 10 Days (2003)
Imagine two people pretending to be in love for totally opposite reasons. That is basically the core of How to Lose a Guy in 10 Days. Andie Anderson is trying to drive a man away for an article, and Benjamin Barry bets his co-workers that he can make any woman of their choosing fall in love with him. The result is a wild ride through the ridiculous, often cringey dance of dating, with enough laughs and swoons to keep you hooked. And even though it's slightly predictable, you still want to make sure everyone gets the ending they deserve. It's a slightly older cousin to 10 Things I Hate About You, playing with deception, attraction, and emotional payoff in all the right ways.
Whatever It Takes (2000)
Remember when teen rom-coms were all about wild schemes and questionable advice from your best friend? Whatever It Takes is peak early 2000s teen melodrama. Ryan is the nerdy guy crushing on the most popular girl in school, and Chris is the hot jock who wants the artsy girl next door, who just so happens to be Ryan’s best friend, Maggie. So, they team up and coach each other on how to win their respective crushes. Obviously, things don’t go as planned. It hits that same sweet spot as 10 Things I Hate About You, flipping classic literature (Cyrano de Bergerac by Edmond Rostand) into a high school drama that makes you root for the underdog.
Where To Watch The 10 Best Rom-Coms Like '10 Things I Hate About You'
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