25+ High School Romantic Comedy Movies Like She's the Man

Movies like She’s the Man

If you’re into hilarious, feel-good stories with mistaken identities, outrageous schemes, and plenty of unexpected romance, then you’re definitely looking for movies like “She’s the Man”.

These are the kinds of films where the main character dives headfirst into a crazy plan, often pretending to be someone else, all in the name of ambition, love, or just sheer chaos.

Add in witty comebacks, awkward encounters, and a touch of heart, and you’ve got a recipe for a total rom-com win.

Mean Girls

Cady Heron, fresh from the savannas of Africa (and homeschooled life), lands in the wild jungle that is high school. Enter the Plastics: a glittery, drama-fueled trio led by Regina George, the queen bee of all things pink and passive-aggressive. Cady gets roped into their world of secrets, burn books, and mean-girl politics, while secretly plotting with her artsy new friends to dethrone Regina. It’s like a reality TV show but with cafeteria battles and questionable fashion choices.

As Cady gets sucked deeper into the Plastics’ glamorous chaos, she starts to blur the line between taking Regina down and becoming her. Along the way, there are cringy crushes, hilarious one-liners, and a Halloween party that goes completely off the rails. High school has never been this fierce—or this fetch.

Easy A

Olive Penderghast is just your average high schooler navigating the weird world of teenage drama—until one tiny white lie flips her world upside down. In an attempt to jazz up a boring weekend story, she claims she had an exciting rendezvous, and suddenly, she’s the talk of the school. News travels faster than a viral TikTok, and Olive finds herself with a scandalous new reputation that she didn’t exactly ask for. Instead of clearing things up, she leans into it, rocking a confidence she never knew she had, complete with a wardrobe makeover.

As her faux reputation spirals into hilariously chaotic territory, Olive becomes the go-to girl for helping socially awkward classmates. Her witty comebacks and clever scheming turn her into an unexpected icon, but it’s not all fun and games. The mounting lies start to take a toll on her personal life, friendships, and even her crush-worthy love life. Amidst the comedy and chaos, Olive has to figure out how to set things right without totally losing herself—or her sense of humor.

10 Things I Hate About You

Meet Kat Stratford, a whip-smart, no-nonsense high schooler who has zero time for romance—or anyone, really. Meanwhile, her younger sister Bianca is the total opposite: bubbly, popular, and itching to date. The catch? Their dad has a strict rule—Bianca can only date if Kat does. Enter Cameron, a sweet, lovestruck newbie who’s got his eye on Bianca. To make his dream come true, Cameron and his scheming buddy hatch a wild plan: get the mysterious bad boy, Patrick Verona, to woo Kat.

Patrick’s got charm to spare, but Kat’s not exactly an easy sell. What follows is a rollercoaster of snarky banter, unexpected chemistry, and a whole lot of high school chaos. Between extravagant displays of affection, cringe-worthy misunderstandings, and a few heartfelt moments that sneak in when you least expect them, Kat and Patrick’s story is anything but ordinary. And while everyone’s busy plotting, romancing, and being dramatic, love starts showing up in the most surprising places.

The DUFF

Bianca Piper is your average, no-nonsense high schooler who’s perfectly fine flying under the radar—until her charming, smug neighbor Wesley drops a truth bomb: she’s the “DUFF” (Designated Ugly Fat Friend) of her squad. Basically, the approachable one who makes her prettier friends seem even prettier. Ouch. Determined to shake the label, Bianca ropes Wes into helping her transform her image, despite the fact that they constantly bicker like an old married couple.

Cue a whirlwind of awkward attempts at makeovers, hilarious school drama, and Bianca’s mission to prove she’s more than some lame acronym. While Wes helps Bianca step out of her comfort zone, sparks start to fly—because obviously, that’s what happens when frenemies spend way too much time together. Meanwhile, Bianca has to dodge the school queen bee and her snarky antics while figuring out how to be true to herself in a world obsessed with labels.

Clueless

Cher Horowitz is the queen bee of Beverly Hills High—super stylish, a total social butterfly, and more than a little clueless about real-world problems. She’s living her best life matchmaking teachers, throwing epic parties, and delivering epic one-liners, all while navigating high school with her bestie, Dionne. But when she decides to take Tai, the awkward new girl, under her wing, Cher’s flawless social life takes a chaotic turn. Suddenly, her well-intentioned plans to transform Tai into a mini-me spark unexpected drama.

Meanwhile, Cher’s ex-stepbrother Josh—who’s way too smart and way too opinionated for her taste—keeps showing up to challenge her perspective on, well, everything. Between makeover mishaps, high school crushes, and her realization that maybe her perfectly curated world isn’t as perfect as she thought, Cher starts to see things in a new light. Of course, she does it all while rocking iconic outfits and delivering some of the sassiest comebacks ever.

And there you have them, folks, the 25+ best hilarious over-the-top high school romantic comedy movies like She’s the Man you should watch today.

25+ High School Romantic Comedy Movies Like She’s the Man