Best high school teen rom-coms of all time

By Mariel Turner 12:04pm PDT, Oct 9, 2022

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Get ready to feel old. "She's All That" star Rachael Leigh Cook's 43rd birthday is on Oct. 4, 2022, so to celebrate, Wonderwall.com is running down our all-time favorite high school rom-coms! The iconic 1999 teen movie "She's All That" starring Rachael Leigh Cook and Freddie Prinze Jr. had it all: a beautiful dorky girl, a sensitive popular guy, a stupid bet, prom and all the drama in between. Audiences loved it so much, it reached No. 1 at the box office in its first week of release. Given just how iconic it was, it's no surprise that a gender-swapped remake debuted in 2021.

Keep reading for more of the very best teen romance films…

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A reimagining of a classic fairytale set in the early aughts? Umm… count us in! 2004's "A Cinderella Story" stars Hilary Duff as Sam Montgomery, a teenage outcast who, under the screen name PrincetonGirl818, has a secret AIM-based relationship with a fellow teen who goes by Nomad. As their relationship deepens, they decide to meet in person at the Halloween Ball — where Sam realizes that her mystery man is none other than Austin Ames (Chad Michael Murray), the most popular guy in school. Throughout the course of the flick, we see Sam struggle with whether or not to reveal her true identity to Austin. Just as she decides to put her heart on the line, we come to realize that her evil stepsisters have a plan of their own in the works.

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Teen rom-coms might have briefly fallen out of style, but they're back and better than ever — as proven by "To All the Boys I've Loved Before." The movie based on the book of the same name immediately became a must-see hit when it dropped on Netflix in 2018 thanks to its witty dialogue, refreshing casting and charming plot. Lana Condor stars as Lara Jean Covey, a high school junior who's written love letters to all her crushes instead of telling them how she felt. When the letters are stolen and mailed out, Lara starts to pretend-date popular classmate Peter Kavinsky, played by Noah Centineo, as a distraction. Of course, their fake romance soon becomes the real thing. Can't get enough? It's spawned two sequels.

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What happens when you've freshly graduated from high school but you've yet to profess your love to the girl of your dreams? 1999's "Can't Hardly Wait" explores this dilemma. Ethan Embry stars as Preston Meyers, an unpopular nice kid who hopes to tell his longtime love, Amanda Beckett (Jennifer Love Hewitt), how he feels before he leaves for a writing fellowship in Boston. As luck would have it, though, Preston and Amanda keep missing each other — despite both being at the same party!

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Hilary Duff wasn't the only teen queen of the early aughts! In 2003's "Freaky Friday" — which is a reimagining of the 1976 film of the same name — Lindsay Lohan shines as rebellious teen rocker Anna Coleman, who wakes up one day in mom Tess Coleman's (Jamie Lee Curtis) body. The stakes are high for the Coleman women — not only does Anna have a pivotal audition coming up, but Tess is one day away from her wedding! Amidst their constant bickering and efforts to reverse the spell, Anna must also grapple with her growing crush on misunderstood heartthrob, Jake (Chad Michael Murray), while in her mother's body.

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Our hearts melted when Heath Ledger serenaded Julia Stiles on the soccer field in "10 Things I Hate About You." The 1999 flick is the perfect high school romance movie with its witty one-liners, heartfelt poems, fantastic source material (Shakespeare's "The Taming of the Shrew") and all-star cast (Heath, Julia, Joseph Gordon-Levitt, Gabrielle Union). In fact, "10 Things I Hate About You" was so great that it opened at No. 2 at the box office during its first weekend right behind "The Matrix."

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What better way to exact revenge on a serial cheater than by making him genuinely fall for a girl… before you rip them apart? 2006's "John Tucker Must Die" — which stars Jesse Metcalfe as the playboy in question — explores this unideal scenario. When three popular girls from disparate cliques (Sophia Bush, Arielle Kebbel, Ashanti) come to realize their supposedly doting boyfriend is actually dating all three of them, they recruit new girl Kate (Brittany Snow) to help them break his heart. By posing as the girl of his dreams, Kate gets John to begin to fall in love with her — but despite initially being on board with the plan, Kate begins to grow a conscience.

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A high school rom-com list without "Clueless"? As if! "Clueless" truly defined a generation. We lived for the sweet romance between Cher, played by the perfect Alicia Silverstone, and her ex-stepbrother Josh, played by an adorable Paul Rudd. Add the amazing wardrobes, fabulous teen life and iconic '90s language and "Clueless" is the perfect teen film.

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We might have come to know and love Shane West for his brooding portrayal of bad boy-turned-good guy Landon Carter in "A Walk to Remember," but two years earlier, he took on a much more lighthearted role! 2000's "Whatever It Takes" — a modern retelling of Edmond Rostand's "Cyrano de Bergerac" — stars Shane as geeky teen Ryan Woodman and James Franco as dimwitted jock Chris Campbell. Recognizing that they occupy two disparate social circles, the boys agree to help each other win the affections of their crushes — Ryan's into ultra popular Ashley Grant (Jodi Lyn O'Keefe) while Chris has the hots for endearingly bookish Maggie Carter (Marla Sokoloff). Their plan, however, begins to go awry when they realize they might be in pursuit of the wrong girls.

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You're a part-time lover and a full-time friend! 2007's "Juno" is a heartwarming coming-of-age flick about a teenager who must decide what to do after finding out she's pregnant. Elliot Page stars as Juno MacGuff, who, despite initially contemplating getting an abortion, ultimately agrees to a closed adoption with a seemingly happy couple (Jennifer Garner and Jason Bateman). In addition to feeling the pressure of having to care for another life, Juno also comes to realize her own growing feelings for Paulie Bleeker (Michael Cera), her boyfriend and the father of her baby.

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Oh, the aughts — a truly magical time for the good ol' high school romantic comedy! Based loosely on William Shakespeare's "A Midsummer Night's Dream," 2001's "Get Over It" stars Ben Foster as Berke Landers, a heartbroken high school student who wants nothing more than to win back his ex-girlfriend (Melissa Sagemiller). Thanks to the help of Kelly Woods (Kirsten Dunst), his best friend's younger sister, Berke joins the school musical in an effort to be closer to his ex. What Berke doesn't account for, however, is that the increased time he's been spending with Kelly makes him see her in a new light.

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Aw, "Sixteen Candles" — what many (including us) would consider to be the quintessential teen romance film. After a run of bad luck, nerdy sophomore Samantha, played by '80s teen queen Molly Ringwald, ultimately gets the perfect 16th birthday gift when she shares a kiss over a cake with her senior knight in shining armor, played by Michael Schoeffling. The 1984 movie, directed by John Hughes and co-starring Anthony Michael Hall, is a must-see for any rom-com fan.

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Quincy McCall and Monica Wright might end up married by the end of "Love and Basketball," but their romance started years before while they were in high school. The 2000 movie about high school sweethearts has it all: the signature prom scene, funny '90s lingo and a "first time" moment that may be the sweetest in Hollywood. Starring a young Sanaa Lathan and Omar Epps, "Love & Basketball' is not to be missed.

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Amanda Bynes is charismatic in this romantic comedy inspired by William Shakespeare's "Twelfth Night." 2006's "She's the Man" — which also stars Channing Tatum, Laura Ramsey and Alex Breckenridge — follows teenager Viola Hastings, who devises a plan to pose as her twin brother, Sebastian (who's off pursuing a music career in London), after the all-girls soccer team at her high school gets cut. Viola strikes a deal with her roommate, Duke Orsino: If he helps her make the boys team, she'll help him get the girl he's long been crushing on. Of course, things go awry when Viola begins to develop feelings for Duke herself!

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A high school romantic comedy that's equally, if not more focused on the experiences of the parents than the teenagers? That's a film we'd love to see! 2018's "Blockers" stars Leslie Mann, John Cena and Ike Barinholtz as Lisa, Mitchell and Hunter, three parents who, after finding out their daughters — who are best friends — made a pact to lose their virginity on prom night, make it their mission to intercept it. But as the night progresses, Lisa, Mitchell and Hunter come to question the intentions behind their mission.

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We love "Love, Simon" for taking the teen rom-com story and reviving it in the best way possible. The heartfelt films centers on a cute, popular guy (played by Nick Robinson) who comes to terms with his sexuality and finds love with a fellow male classmate. "Love, Simon" — the first film by a major Hollywood studio to focus on a gay teenage romance — grossed $66 million worldwide. It's funny, sweet and wonderfully acted — all the ingredients for a flawless rom-com.

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The 1978 high school-set musical "Grease" is legendary for its fabulous songs, perfect choreography and iconic love story. The movie follows T-Bird Danny Zuko, played by a young and super-attractive John Travolta, and Australian transfer student Sandy Olsson, played by a gorgeous Olivia Newton-John, as they navigate love and friendship. "Grease" might be more than 40 years old, but it's just as amazing today as it was back then. Fun fact: The "Grease" soundtrack was the second bestselling album of the year in 1978.

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An early aughts movie starring Christina Milian? We should consider ourselves blessed. 2003's "Love Don't Cost A Thing" revolves around Alvin Johnson (Nick Cannon), a geeky and gifted high school student with a vast knowledge of engineering who strikes up a deal with popular girl Paris Morgan (Christina): He'll fix her mom's damaged car so long as they date for two weeks. After Paris agrees, Alvin is quickly thrust to the top of the social ladder, but he soon realizes that maintaining that status may come at a cost.

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Each "High School Musical" movie is perfection in its own right, but there's something particularly captivating about the second installment. "High School Musical 2," which debuted in 2007, sees the gang working at a New Mexico country club for the duration of summer. However, while the experience was meant to bring them all closer, Troy Bolton (Zac Efron) becomes wrapped up in the superficiality of it all — from hanging around Sharpay Evans (Ashley Tisdale) to neglecting his friends in an effort to network with basketball bigwigs. A particular relationship that suffers as a result? Troy's romance with Gabriella (Vanessa Hudgens), who doesn't like the person he's become.

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"Never Been Kissed" is a unique high school rom-com considering neither of its main characters are actually students. In the 1999 flick, 25-year-old reporter Josie, played by the lovable Drew Barrymore, returns to high school as an undercover student for a story. There, she meets and falls for her teacher, who's played by Michael Vartan. "Never Been Kissed" has an all-star cast (Drew, Michael, Molly Shannon, John C. Reilly, James Franco, Jessica Alba) and a super-cute story, all contributing to its $84 million in earnings.

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In addition to spawning several noteworthy quotes and catchphrases, 2004's "Mean Girls" gave us an adorable teen romance. Lindsay Lohan stars as transfer student Cady, who finds herself embroiled with the meanest girls in school: the Plastics (Rachel McAdams, Amanda Seyfried, Lacey Chabert), spearheaded by queen bee Regina George. As Cady copes with her flawed moral compass, she develops feelings for high school cutie Aaron Samuels (Jonathan Bennett), who, unfortunately, happens to be Regina's ex.

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The film that started it all! 1999's "American Pie" stars Jason Biggs, Eddie Kaye Thomas, Thomas Ian Nicholas and Chris Klein as a group of friends who make a pact to lose their virginity before graduating high school. While there's no shortage of raunchy scenes in the coming-of-age sex comedy, it's surprisingly filled with a ton of heart. (Jim and Michelle forever.)

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We loved the sweet romance between cheerleader Megan Bloomfield (played by Natasha Lyonne) and her fellow conversion therapy attendee Graham Eaton (played by Clea DuVall) in 2000's "But I'm a Cheerleader." The teen satire follows Megan after her family sends her away to "cure" her lesbianism. There, she finds love with the charismatic Graham. "But I'm a Cheerleader" is unique, hilarious and endearing, all qualities that make it one of the best.

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Sure, we all love Duchess Kate and Duchess Meghan, but Princess Mia Thermopolis is our hands-down favorite royal. In 2001's "The Princess Diaries," American high school student Mia not only finds out she's actually a European royal but finds love with her best friend's brother, fellow classmate Michael Moscovitz. The Disney teen movie, which grossed over $165 million, starred future A-listers Anne Hathaway and Mandy Moore and the legendary Julie Andrews. 10/10!

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Who didn't have a crush on Michael Cera back in the day?! In 2008, the Canadian cutie starred in "Nick and Norah's Infinite Playlist" alongside Kat Dennings. The romantic comedy, which is based on Rachel Cohn's novel of the same name, revolves around Nick, a heartbroken bass player who can't stop thinking about his ex-girlfriend, and Norah, the daughter of a respected record producer who's equally as passionate as Nick about music. One fateful night, Nick and Norah find themselves traversing around the city together looking for Norah's drunk friend (Ari Graynor). Of course, sparks begin to fly between the two unsuspecting teens.

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Get the tissues ready! "A Walk to Remember" might be the sweetest, saddest teen romance movie we've ever seen. The 2002 film follows Landon Carter and Jamie Sullivan as they fall in love and confront her battle with leukemia. We nearly ran out of tissues watching Landon kiss Jamie after her breathtaking performance in the high school play. Starring Mandy Moore in her breakout role and Shane West, "A Walk to Remember" is a true classic.

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Falling in love with a guy a year older than you who's about to go off to college is complicated enough. Throw in the added drama that he's the older brother of your best friend, and you've got a total disaster on your hands. In 2018's "The Kissing Booth" — the first of three installments in the franchise — Joey King stars as Elle Evans, a teen who unexpectedly finds herself in a secret romance with her lifelong best friend Lee Flynn's (Joel Courtney) older brother, Noah (Jacob Elordi). To Elle's dismay, Lee is less than willing to accept his bestie's blooming relationship because it violates the rules of their friendship. Yikes.

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Our list wouldn't be complete without this John Hughes film! "Pretty in Pink" is the ultimate teen rom-com thanks to Brat Pack members Molly Ringwald and Andrew McCarthy and scene-stealer Jon Cryer. Molly stars as Andie, an artsy outcast who falls for Blane, her popular and rich classmate. Their relationship faces an uphill battle thanks to their different social statuses. Meanwhile, Andie's dorky best friend, Duckie, is secretly in love with her. Released in 1986, "Pretty in Pink" is a cult classic that everyone should check out.

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"Easy A" has to be one of the most creative teen films we've ever seen. Loosely inspired by "The Scarlet Letter," "Easy A" follows Olive, a clean-cut student who decides to spice things up and lie about losing her virginity. Her little white lie soon turns her life upside down, but Olive finds happiness (and love) with the school mascot, Todd. "Easy A" is the film that helped propel Emma Stone to super-stardom and solidified Penn Badgley as a total heartthrob.

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What happens when you mix a classically trained ballet dancer and a med school-bound hip-hop kid from opposite worlds? True love, of course! Sara Johnson and Derek Reynolds' love takes center stage in 2001's "Save the Last Dance," in which they overcome different backgrounds, the death of a loved one, gang associations and teen angst. Julia Stiles and Sean Patrick Thomas shine in this teen-focused rom-com.

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So what if "Spider-Man: Far From Home" is a superhero flick?! The Marvel movie, which was released in 2019, stars Tom Holland as high schooler Peter Parker/Spider-Man, who goes on a class trip to Europe in hopes of growing closer to his longtime crush, MJ (Zendaya). Of course, as soon as they touch down in Italy, Peter is recruited by Nick Fury (Samuel L. Jackson) to put a stop to some of the diabolical villains threatening the continent. The film follows Peter as he struggles with juggling his duties as Spider-Man with his hopes to get the girl of his dreams.

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2019's "The Perfect Date" stars Noah Centineo as Brooks Rattigan, a technology-savvy teen who creates an app that allows him to pose as a fake date, which he uses to earn money for college. His seemingly foolproof plan, however, begins to unravel when he falls for a girl he was paid to take out.

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From its super-cute story to its legendary theme song, "Drive Me Crazy" is a blast across the board. The 1999 movie stars Melissa Joan Hart (a '90s icon) and Adrian Grenier (our childhood crush) as next-door neighbors who decide to fake-date each other to make their real crushes jealous. The twosome soon realize that they already have true love — with each other. "Drive Me Crazy" was a major hit, grossing over $22 million — plus it gave us one of Britney Spears' best songs!

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"Say Anything" has a ton of moments that make it one of our favorite teen rom-coms of all time, but the most iconic has to be the boombox scene. The grand gesture we've all been waiting for IRL! After losing his girlfriend Diane, Lloyd Dobler plays "In Your Eyes" by Peter Gabriel outside of her window to show his love. Starring John Cusack and Ione Skye, "Say Anything" received rave reviews from critics and audiences when it opened in 1989.

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If you had the chance to go back in time and redo it all, would you? "17 Again" considers this wild possibility. The romantic comedy follows 37-year-old Mike O'Donnell (Matthew Perry), a washed up high school basketball star who gave up a promising career to marry his pregnant girlfriend and raise their child. Now, nearly 20 years and another kid later, Mike's grown to resent his wife (Leslie Mann) and the life they've created. When Mike is inexplicably transformed back into his 17-year-old self (Zac Efron), he gets the chance to right his wrongs and fix his past — which, we come to realize, may jeopardize his present.

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"Dope" is definitely one of the dopest movies we've seen so far. The 2015 indie flick has a hilarious and heartfelt story, phenomenal acting and the perfect soundtrack, making it one of the best. "Dope" follows Malcolm Adekanbi, a geeky teen from Inglewood, California, who falls for Nakia, a cool and classy girl who's struggling to get her GED. Their sweet romance is complicated when Malcolm is forced to help out a drug dealer acquaintance. Shameik Moore and Zoe Kravitz excel in this feel-good film, which was produced by Forest Whitaker.

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2011's "Prom" explores several intersecting stories about teenagers as they prepare for what's supposed to be the most magical night of their young lives. "Friday Night Lights" alum Aimee Teegarden stars in one storyline as Nova Prescott, an innocent, rule-abiding senior who begins to fall for Jesse Richter (Thomas McDonell), a misunderstood guy at school. Nicholas Braun, Danielle Campbell, DeVaughn Nixon, Cameron Monaghan and Nolan Sotillo also appear in this high school rom-com.

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Despite having aspects of a romantic comedy, this film also marks one of Hilary Duff's more dramatic roles. 2004's "Raise Your Voice" stars the teen queen as Terri Fletcher, a young girl from Flagstaff, Arizona, who dreams of being a singer-songwriter. Following the tragic death of her older brother, Paul, who was also her biggest supporter, Terri decides to attend a prestigious summer music program in Los Angeles, despite her overbearing father's wishes. There, Terri hones her craft and falls in love with a fellow musician named Jay (Oliver James).

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The 1982 coming-of-age comedy-drama "Fast Times at Ridgemont High" follows Stacy Hamilton (Jennifer Jason Leigh), a beautiful teen who majorly lacks experience in all things dating. After taking advice from pal Linda Barrett (Phoebe Cates), Stacy finds herself in a complex love triangle with boy-next-door Mark Ratner (Brian Backer) and his more confident companion Mike Damone (Robert Romanus). Simultaneously, the lauded high school romantic comedy follows Sean Penn's Jeff Spicoli, Stacy's surfer classmate who butts heads with their principal, Mr. Hand (Ray Walston).

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After meeting by happenstance at a high school party, teens Dave Hodgman (Dylan O'Brien) and Aubrey Miller (Britt Robertson) strike up a conversation that leads to so much more. While Dave is initially hung up on Jane (Victoria Justice), the girl in his friend group who's long been the object of his affection, he begins to develop feelings for Aubrey. Soon, Dave and Aubrey find themselves agreeing to lose their virginity to one another… a decision that seems simple, in theory. 2012's "The First Time" explores first loves, first heartbreaks and the power of first experiences.

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No high school rom-com list would be complete without this classic! 1963's "Bye Bye Birdie" is one of the first teen romance movies to come out of Hollywood. The legendary musical stars Ann-Margret as Kim MacAfee, a lucky high school girl who's selected to kiss young rock 'n' roll star Conrad Birdie before he heads off to war. The kiss causes problems for her high school sweetheart Hugo Peabody, played by Bobby Rydell, but the couple reunites in the end. "Bye Bye Birdie" delighted audiences back in the '60s and continues to do so today.

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It's no fun being the girl in the friend group that no one wants to date — and it's especially no fun when you're given a totally demeaning nickname. 2015's "The Duff" stars Mae Whitman as Bianca, the designated uglier, less attractive friend of her pretty girlfriends who enlists help from the hottest guy in school, Wesley (Robbie Amell), to become more confident. A seemingly simple plan grows increasingly complex when Bianca and Wesley realize they might have feelings for each other.