10 Rom Coms That Will Take You Back To High School

High school — where first crushes, awkward moments, and new experiences shaped our teenage years. It’s no wonder romantic comedies often set their stories during this time, capturing the highs and lows with both humor and heart. Whether you want to revisit your own high school days or just enjoy a good love story, these 10 rom-coms will take you right back.

Clueless (1995)

Clueless — often considered the blueprint for the modern high school rom-com — takes Jane Austen’s Emma and gives it a Beverly Hills twist. Cher Horowitz, played by Alicia Silverstone, is a stylish, well-meaning rich girl who’s a bit clueless (pun intended) as she navigates love, friendship, and way harsh teachers. The 1995 classic perfectly captures the high school experience including crushes, cliques, makeovers, and all the drama. And it delivers a sharp, quotable script that had us all saying “As if!” for years.

She’s All That (1999)

She’s All That is the ultimate 90s high school movie cliché fest but in the best way possible. You’ve got your popular jock Zack (Freddie Prinze Jr.) making a bet that he can turn any girl into prom queen material, and of course, he picks the “nerdy” art girl Laney (Rachael Leigh Cook) – because apparently, all it takes to be unpopular is glasses and paint-splattered overalls. The whole makeover trope is cranked up to eleven, complete with that classic “she was beautiful all along” reveal that had every awkward teen dreaming of their glow-up moment.

10 Things I Hate About You (1999)

10 Things I Hate About You is the teenage rom-com that made Shakespeare cool again (as if he wasn’t already). The movie drops The Taming of the Shrew smack in the middle of a 90s high school with paintball dates, prom drama, awkward parent moments, and the most swoon-worthy rooftop serenade in cinema history. You’ve got Heath Ledger stealing hearts as the bad boy with a secret soft side, and Julia Stiles nailing it as the sharp-tongued, combat-boot-wearing Kat who’s too smart for your average teen movie heroine. It’s got all the high school rom-com staples, including the classic “enemies to lovers” vibe, but with whip-smart dialogue and characters.

Pretty In Pink (1986)

Pretty in Pink is the 1986 John Hughes classic that wrote the blueprint for every high school rom-com that came after. The iconic movie nails that whole “wrong side of the tracks” vibe with Molly Ringwald’s Andie — a working-class girl with killer style — crushing on Andrew McCarthy’s rich-boy Blane. It’s got all the good stuff: best friend drama, mean popular kids, and that gut-wrenching “will they or won’t they?” tension leading up to prom night. But what makes this movie special is how it tackles class differences and authenticity, all while serving up some seriously iconic 80s fashion moments.

The Duff (2015)

When it was released in 2015, The Duff felt like a fresh take on the typical high school rom-com. It follows Bianca, played by Mae Whitman, a teen who realizes she’s been named the “Designated Ugly Fat Friend” of her friend group. She teams up with her jock neighbor Wesley (Robbie Amell) to shake off that nasty label. The movie nails how brutal high school can be, but also has an awesome message about loving yourself and telling those toxic stereotypes to take a hike.

She’s the Man (2006)

She’s the Man brings Shakespeare’s “Twelfth Night” to high school. Amanda Bynes plays a teen girl who pretends to be her twin brother to join an all-boys soccer team because, in typical movie logic, that’s somehow easier than fighting for a spot on the girls’ team. Naturally, she falls for her roommate, who likes another girl, and then develops a crush on Amanda’s male persona. It’s a hilarious mix of secret identities and awkward locker room scenes. The whole premise is delightfully ridiculous, with Bynes nailing the role as she struggles to “be a dude,” and Channing Tatum delivering peak early 2000s heartthrob vibes.

The Kissing Booth (2018)

The Kissing Booth is one of Netflix’s most successful rom-coms. The movie follows Joey King’s Elle, a teen who’s head over heels for her best friend’s older brother, Noah (played by Jacob Elordi), even though their BFF code makes him off-limits. Packed with all the classic teen rom-com elements — secret makeout sessions, pool parties, and plenty of teenage angst — it’s the kind of story that makes you want to curl up with some popcorn and revisit those electric high school days.

Easy A (2010)

Easy A takes on The Scarlet Letter and brilliantly captures the hypocrisy of high school life. Emma Stone shines as Olive, a teen who embraces a fake bad reputation and turns the rumor mill to her advantage. The movie is packed with witty one-liners, hilarious misunderstandings, and Penn Badgley being adorably supportive.

Can’t Hardly Wait (1998)

Can’t Hardly Wait is the quintessential 90s high school party film. It follows a massive graduation party where everyone is eager to close their high school chapters in one unforgettable night. The film features the classic mix of characters: the nerdy guy secretly in love with the popular girl, the jock reeling from a breakup, and a host of side characters getting into all sorts of mischief. Plus, the soundtrack is so good, it’ll have you reaching for your old CDs.

Never Been Kissed (1999)

Never Been Kissed is a delightfully absurd yet incredibly fun twist on the high school rom-com. Drew Barrymore stars as Josie, a 25-year-old reporter who goes undercover as a high school student (because that’s totally plausible, right?). The movie hits all the classic high school movie beats—cool kids, outcasts, and plenty of awkward moments—but adds a hilarious twist with an adult pretending to be a teenager. The real charm lies in watching Josie get a second chance to redo her disastrous first high school experience, complete with a surprisingly sweet romance with her English teacher (which somehow manages to be way less creepy than it sounds).