The best teen high school romantic comedies of all time (2023)

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Prepare to feel old. "She's All That" star Rachael Leigh Cook's 43rd birthday is October 4, 2022, so to celebrate,Wonderwall.comis running out of our all-time favorite romantic comedies. The iconic 1999 teen movie "She's All That," starring Rachael Leigh Cook and Freddie Prinze Jr., had it all: a beautiful stupid girl, a sensitive popular guy, a stupid bet, prom, and everything in between. drama in between. Audiences loved it so much that it reached No. 1 at the box office in its first week of release. Given how iconic it was, it's no surprise that a gender-swap remake debuted in 2021.

Read more about the best romantic movies for teens...

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A reimagining of a classic fairy tale set in the early years? Hmm... Count on us! Stars of 2004's "A Cinderella Story"Hilary Duffas Sam Montgomery, a teenage outcast who, under the screen name PrincetonGirl818, has a secret AIM-based relationship with a fellow teenager calling himself Nomad. As their relationship deepens, they decide to meet in person at the Halloween dance, where Sam realizes that her mystery man is none other than Austin Ames (Chad Michael Murray), the most popular guy in school. Throughout the film, we see Sam struggling with whether or not to reveal his true identity to Austin. Just when she decides to put her heart on the line, we discover that her wicked stepsisters have their own plan in motion.

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Teen romantic comedies may have briefly gone out of style, but they're back and better than ever, as "To All The Boys I've Loved Before" proves. The film based on the book of the same name immediately became an unmissable hit when it was released on Netflix in 2018, thanks to its witty dialogue, refreshing cast and enchanting storyline. Lana Condor stars as Lara Jean Covey, a high school student who writes love letters to all her crushes instead of telling them how she feels. When the letters are stolen and sent, Lara begins pretending to date her popular classmate Peter Kavinsky, played by Noah Centineo, as a distraction. Of course, her fake romance soon turns into the real thing. Can't get enough? It spawned two sequels.

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What happens when you've just graduated high school but still haven't declared your love for the girl of your dreams? 1999's Can't Hardly Wait explores this dilemma. Ethan Embry stars as Preston Meyers, a nice but unpopular kid hoping to tell his longtime love, Amanda Beckett (Jennifer wants a Hewitt), how you feel before leaving for a scholarship in Boston. Thankfully though, Preston and Amanda still miss each other even though they're both at the same party!

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Hilary DuffShe wasn't the only teen queen of the early years! In 2003's "Freaky Friday", which is a retelling of the 1976 film of the same name,Lindsay Lohanshines as rebellious teen rocker Anna Coleman, who one day wakes up in the body of her mother Tess Coleman (Jamie Lee Curtis). The stakes are high for the Coleman women: not only does Anna have a crucial audition coming up, but Tess is a day away from her wedding! Amidst their constant bickering and efforts to reverse the spell, Anna must also deal 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 football field in "10 Things I Hate About You." The 1999 film is the perfect school romance with its smart lines, heartfelt poems, fantastic material (Shakespeare's The Taming of the Shrew) and an all-star cast (Heath, Julia, Joseph Gordon-Levitt, Gabrielle Union). 🇧🇷 In fact, "10 Things I Hate About You" was so good that it debuted at No. 2 at the box office during its opening weekend, behind only "The Matrix."

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What better way to get revenge on a serial cheater than to make him genuinely fall in love with a girl... before breaking them up? 2006's "John Tucker Must Die," starring Jesse Metcalfe as the playboy in question, explores this less-than-ideal scenario. When three popular girls from different groups (Sophia Bush, Arielle Kebbel, Ashanti) realize that their supposedly smitten boyfriend is actually dating all three of them, they enlist new girl Kate (Brittany Snow) to help them break her heart. By impersonating the girl of her dreams, Kate manages to make John start to fall in love with her, but despite initially agreeing to the plan, Kate starts to come to her senses.

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A list of high school rom-coms without "Clueless"? As if! "Clueless" truly defined a generation. We live for the sweet romance between Cher, played by the perfectAlicia Silverstone, and his former half-brother Josh, played by an adorable Paul Rudd. Add in the awesome clothes, fabulous teen life and iconic 90s lingo and "Clueless" is the perfect teen movie.

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We may have known and loved Shane West for his haunting 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! A modern take on Edmond Rostand's "Cyrano de Bergerac", 2000's "Whatever It Takes" stars Shane as nerdy teen Ryan Woodman andJames Francoas goofy jock Chris Campbell. Recognizing that they occupy two disparate social circles, the guys agree to help each other win the affections of their crushes: Ryan likes the ultra-popular Ashley Grant (Jodi Lyn O'Keefe), while Chris likes the lovely Maggie Carter (Marla Sokoloff). 🇧🇷 🇧🇷 However, their plan starts to go awry when they realize they might be chasing the wrong girls.

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You are a part-time lover and a full-time friend! 2007's "Juno" is an emotional coming-of-age film about a teenager who must decide what to do after discovering she is pregnant. Elliot Page stars as Juno MacGuff, who, despite initially contemplating an abortion, eventually agrees to a gated adoption with a seemingly happy couple (Jennifer Garner and Jason Bateman). In addition to feeling the pressure of having to take care of another life, Juno also realizes her growing feelings for Paulie Bleeker (Michael Cera), her boyfriend and the father of her baby.

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Oh, the stuff: a truly magical moment for a good ol' high school rom-com! Loosely based 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). With the help of Kelly Woods (Kirsten Dunst), his best friend's younger sister, Berke joins the school musical in an attempt to get closer to his ex. What Berke doesn't take into account, however, is that the increased time he spends with Kelly makes him see her in a new light.

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Wow, "Sixteen Candles" - what many (us included) would consider the quintessential teen romance movie. After a streak of bad luck, nerdy sophomore Samantha, played by '80s teen queen Molly Ringwald, finally lands the perfect 16th birthday present when she kisses the cake with her knight in shining armor, played by Michael Schoeffling. The 1984 film, directed by John Hughes and co-starring Anthony Michael Hall, is a must-see for any fan of romantic comedies.

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Quincy McCall and Monica Wright may end up getting married at the end of "Love and Basketball," but their romance began years earlier when they were in high school. The 2000 movie about high school sweethearts has it all: the prom scene, funny '90s slang, and a "first time" moment that might just be Hollywood's sweetest. 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". Also starring Channing Tatum, Laura Ramsey and Alex Breckenridge, 2006's "She's the Man" follows teenager Viola Hastings, who devises a plan to impersonate her twin brother, Sebastian (who is pursuing a music career in London). women's soccer team is eliminated. Viola makes a deal with her roommate, Duke Orsino: if he helps her make the men's team, she'll help him get the girl he's had a crush on for a long time. Of course, things go awry when Viola starts to develop feelings for Duke herself!

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A high school rom-com that focuses as much, if not more, on the experiences of parents as it does teenagers? This is a movie we would love to see! 2018's "Blockers" stars Leslie Mann,John Cenaand Ike Barinholtz as Lisa, Mitchell and Hunter, three fathers who, after discovering that their daughters, who are best friends, have made a pact to lose their virginity on prom night, are tasked with intercepting it. But as the night progresses, Lisa, Mitchell and Hunter question the intentions behind their mission.

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We love "Love, Simon" for taking the teen romantic comedy story and bringing it to life in the best possible way. The heartwarming films center on a handsome and popular boy (played by Nick Robinson) who comes to terms with his sexuality and finds love with a classmate. "Love, Simon," the first major Hollywood studio film to focus on gay teen 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 musical "Grease" is legendary for its fabulous songs, impeccable choreography and iconic love story. The film follows T-Bird Danny Zuko, played by a young and super attractiveJohn Travolta, and Australian transfer student Sandy Olsson, played by the beautiful Olivia Newton-John, as they navigate love and friendship. "Grease" may be over 40 years old, but it's just as amazing today as it was back then. Fun fact: The soundtrack to "Grease" was the second best-selling album of the year in 1978.

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One of the first starring filmscristina milian🇧🇷 We should consider ourselves blessed. 2003's "Love Don't Cost A Thing" revolves around Alvin Johnson (nick cannon), a nerdy and talented high school student with a vast knowledge of engineering who makes a deal with popular girl Paris Morgan (Christina): he will fix her mother's damaged car, as 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 can come at a cost.

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Every "High School Musical" movie is perfect on its own, but there's something particularly captivating about the second part. "High School Musical 2", released in 2007, sees the gang working at a New Mexico country club during the summer. However, although the experience was intended to bring them closer, Troy Bolton (Zac Efron) gets caught up in the superficiality of everything from hanging out with Sharpay Evans (Ashley Tisdale) to neglecting his friends in an effort to hook up with basketball bigwigs. A specific relationship that suffers as a result? Troy's romance with Gabriella (Vanessa Hudgens), who does not like the person he has become.

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"Never Been Kissed" is a unique high school romantic comedy that doesn't consider any of its main characters students. In the 1999 film, 25-year-old reporter Josie, played by the lovelyDrew Barrymore, he returns to high school as an undercover student for a story. There, she meets and falls in love with her teacher, played by Michael Vartan. "I've Never Been Kissed" has an all-star cast (Drew, Michael, Molly Shannon, John C. Reilly,James Franco, Jessica Alba) and a super cute story, which contribute to its $84 million in earnings.

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In addition to generating several notable quotes and catchphrases, 2004's "Mean Girls" provided us with a lovely teen romance.Lindsay LohanShe plays transfer student Cady, who becomes involved with the school's meanest girls: the Plastics (Rachel McAdams, Amanda Seyfried, Lacey Chabert), led by Queen Bee Regina George. As Cady struggles with her faulty moral compass, she develops feelings for handsome high school student Aaron Samuels (Jonathan Bennett), who unfortunately turns out to be Regina's ex.

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The movie that started it all! Stars of 1999 "American Pie"jason biggs, Eddie Kaye Thomas, Thomas Ian Nicholas and Chris Klein as a group of friends who make a pact to lose their virginities before finishing high school. While the coming-of-age sex comedy doesn't lack for raunchy scenes, it's surprisingly full of emotion. (Jim and Michelle forever.)

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We love the sweet romance between cheerleader Megan Bloomfield (played by Natasha Lyonne) and her conversion therapy partner Graham Eaton (played by Clea DuVall) in 2000's "But I'm a Cheerleader." that 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 catchy, 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 favorite royal. In 2001's "The Princess Diaries," American high school student Mia not only discovers that she is actually European royalty, but also finds love with her best friend's brother, her classmate Michael Moscovitz. Disney teen movie, which grossed over $165 million, starred future starsAnne Hathawayymandy mooreand the legendary Julie Andrews. 10/10!

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WhonoWere you in love with Michael Cera in the past? In 2008, the Canadian cutie starred in "Nick and Norah's Infinite Playlist" alongside Kat Dennings. The romantic comedy, based on the novel of the same name by Rachel Cohn, revolves around Nick, a heartbroken bassist who can't stop thinking about his ex-girlfriend, and Norah, the daughter of a respected music producer who is equally passionate. like Nick in the song. One fateful night, Nick and Norah find themselves scouring the city together in search of Norah's drunk friend (Ari Graynor). Of course, sparks start to fly between the two unsuspecting teenagers.

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Prepare the tissues! "A Walk to Remember" may 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 face their battle with leukemia. We almost ran out of tissues watching Landon kiss Jamie after his stunning performance in the high school play. Protagonistmandy moorein its breakout role and Shane West, "A Walk to Remember" is a true classic.

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Falling in love with a guy who's a year older than you and about to start college is hard enough. Add in the added drama of him being your best friend's older brother, and you have 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 teenager who unexpectedly finds herself in a secret affair with her best friend's older brother, Lee Flynn (Joel Courtney). . , Noah (Jacob Elordi). Much to Elle's dismay, Lee is unwilling to accept her best friend's burgeoning relationship because it violates the rules of their friendship. Oh!

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Our list wouldn't be complete without this John Hughes movie! "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 plays Andie, an artistic outcast who falls in love with Blane, her popular and wealthy classmate. Their relationship is facing an uphill battle thanks to their different social statuses. Meanwhile, Andie's goofy best friend Duckie has a secret crush on her. Released in 1986, "Pretty in Pink" is a cult classic that everyone should see.

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"Easy A" has to be one of the most creative teen movies we've ever seen. Loosely inspired by "The Scarlet Letter", "Easy A" follows Olive, an impeccable student who decides to spice things up and lie about losing her virginity. Her little lie soon turns her life upside down, but Olive finds happiness (and love) with the school mascot, Todd. "Easy A" is the movie that helped boostEmma Stoneto stardom and solidifiedPenn Badgleyas a total piece.

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

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So what if "Spider-Man: Far From Home" is a superhero movie? The Marvel film, released in 2019, stars Tom Holland as high school student Peter Parker/Spider-Man, who takes a field trip to Europe in hopes of getting closer to his longtime crush, MJ. 🇧🇷Zendaya🇧🇷 Of course, once they land in Italy, Peter is recruited by Nick Fury (Samuel L. Jackson) to take down some of the diabolical villains threatening the continent. The film follows Peter as he struggles to juggle his duties as Spider-Man with his hopes of landing the girl of his dreams.

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2019's "The Perfect Date" stars Noah Centineo as Brooks Rattigan, a tech-savvy teen who creates an app that allows him to impersonate a fake date, which he uses to earn money for college. However, his seemingly foolproof plan starts to fall apart when he falls in love with a girl he was paid to have.

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From its super cute story to its legendary theme song, "Drive Me Crazy" is a blast in every way. The 1999 film stars Melissa Joan Hart (a '90s icon) andAdrian Grenier(our childhood crush) like neighbors who decide to go on fake dates to make their real crushes jealous. The couple soon realizes that they already have true love, for each other. "Drive Me Crazy" was a huge hit, grossing over $22 million, as well as giving us one of the best Britney Spears songs ever!

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"Say Anything" has many moments that make it one of our favorite romantic comedies of all time, but the most iconic has to be the boombox scene. The grand gesture we've all been waiting for in real life! After losing his girlfriend Diane, Lloyd Dobler plays Peter Gabriel's "In Your Eyes" outside his window to show his love. ProtagonistJuan Cusackand Ione Skye, "Say Anything" received rave reviews from critics and audiences alike when it was released in 1989.

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If you had the opportunity to go back in time and do it all over again, would you do it? "17 Again" considers that wild possibility. The romantic comedy follows 37-year-old Mike O'Donnell (Matthew Perry), a high school basketball star who has given up a promising career to marry his pregnant girlfriend and raise their child. Now, nearly 20 years and another child later, Mike has come to resent his wife (Leslie Mann) and the life they created. When Mike inexplicably transforms into his 17-year-old self (Zac Efron), you have the opportunity to correct your mistakes and fix your past, which, we realized, can compromise your present.

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"Dope" is definitely one of the best movies we've seen so far. The 2015 indie film has a hilarious and heartwarming story, phenomenal acting, and perfect soundtrack, making it one of the best. "Dope" follows Malcolm Adekanbi, a nerdy teenager from Inglewood, California, who falls in love with Nakia, a cool, classy girl struggling to earn her GED. Their sweet romance is complicated when Malcolm is forced to help a notorious drug dealer. Shameik Moore and Zoe Kravitz stand out in this light-hearted film, produced by Forest Whitaker.

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2011's "Prom" explores various crossover stories about teenagers as they prepare for what should be the most magical night of their young lives. "Friday Night Lights" alum Aimee Teegarden stars in a story as Nova Prescott, an innocent, rule-abiding girl who begins to fall in love with Jesse Richter (Thomas McDonell), a misunderstood boy at school. Nicholas Braun, Danielle Campbell, DeVaughn Nixon, Cameron Monaghan and Nolan Sotillo also appear in this high school romantic comedy.

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Despite having aspects of a romantic comedy, this film also marks one of theHilary Duffmore dramatic roles of. 2004's "Raise Your Voice" stars the teen queen as Terri Fletcher, a young woman from Flagstaff, Arizona who dreams of being a singer-songwriter. After 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 father's overbearing 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 dramedy "Fast Times at Ridgemont High" follows Stacy Hamilton (Jennifer Jason Leigh), a beautiful teenager who lacks experience in all things dating. After following the advice of her friend Linda Barrett (Phoebe Cates), Stacy finds herself in a complex love triangle with neighbor Mark Ratner (Brian Backer) and his trusted partner, Mike Damone (Robert Romanus). Simultaneously, the lauded high school romantic comedy follows Sean Penn's Jeff Spicoli, Stacy's surfing classmate who clashes with her principal, Mr. Hand (Ray Walston).

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After meeting by chance at a high school party, teenagers Dave Hodgman (Dylan O'Brien) and Aubrey Miller (Britt Robertson) strike up a conversation that leads to much more. Although Dave is initially obsessed with Jane (Victoria Justice), the girl in his group of friends who has long been the object of his affection, he begins to develop feelings for Aubrey. Soon, Dave and Aubrey agree to lose their virginity to each other... a decision that seems simple on paper. 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! "Bye Bye Birdie", from 1963, is one of the first romantic teen movies to come out of Hollywood. The legendary musical stars Ann-Margret as Kim MacAfee, a lucky high school girl who is selected to kiss young rock 'n' roll star Conrad Birdie before he leaves for war. The kiss causes problems for her high school sweetheart, Hugo Peabody, played by Bobby Rydell, but the two end up reuniting. "Bye Bye Birdie" wowed crowds in the '60s and continues to do so today.

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It's not fun being the girl in your friend group that no one wants to date, and it's especially not fun when you're given a totally demeaning nickname. 2015's "The Duff" stars Mae Whitman as Bianca, the designated ugliest, least attractive friend of their pretty girlfriends who enlists the help of the hottest guy in school, Wesley (Robbie Amell), to boost her confidence.A seemingly simple plan becomes increasingly complex when Bianca and Wesley realize they might have feelings for each other.