Looking for a feel-good movie that perfectly captures the essence of young love? You're in the right place! Our curated list of the top 30 teen and tween romantic comedies from the past 25 years is here to sweep you off your feet. These films have delighted audiences with their charming stories, memorable performances, and timeless tales of high school romance. From classic 90s hits to modern Netflix favorites, each movie brings a unique blend of humor, heart, and the magic of first love.
Whether you're reminiscing about your own high school days or discovering these gems for the first time, these movies promise to entertain and warm your heart. They showcase the ups and downs of teenage romance, the awkwardness of first dates, and the joy of finding that special someone. So grab your popcorn, cozy up, and let these delightful films take you on a nostalgic journey through the trials and tribulations of young love. Dive into our list and find your next favorite Classic teen and Tween romantic comedy Movies!
Classic Teen and Tween Romantic Comedy Movies
1. 10 Things I Hate About You (1999)
Director: Gil Junger
Stars: Heath Ledger, Julia Stiles, Joseph Gordon-Levitt
Description: This modern adaptation of Shakespeare's "The Taming of the Shrew" is set in a high school and follows the tumultuous relationship between a rebellious girl and a charming bad boy. Their romance is complicated by a bet, family dynamics, and social expectations.
Plot: Kat Stratford is a strong-willed teenager who is resistant to romance, but she finds herself falling for Patrick Verona, the new guy in school, who has been paid to date her.
Why should I watch it: The film is a fun, witty, and modern take on a classic story, with memorable performances and sharp dialogue.
IMDb: 7.3
Rotten Tomatoes: 70%
Trailer: 10 Things I Hate About You Trailer
2. Clueless (1995)
Director: Amy Heckerling
Stars: Alicia Silverstone, Paul Rudd, Brittany Murphy
Description: Loosely based on Jane Austen's "Emma," this film follows the life of a wealthy and popular high school girl who takes on the challenge of making over a new student. Cher navigates the ups and downs of high school life while trying to set up her friends and find her own romantic match.
Plot: Cher Horowitz navigates the social scene of a Beverly Hills high school while learning about love and life.
Why should I watch it: "Clueless" is a clever and stylish comedy with a standout performance by Alicia Silverstone, capturing the essence of 90s teen culture.
IMDb: 6.9
Rotten Tomatoes: 81%
Trailer: Clueless Trailer
3. Mean Girls (2004)
Director: Mark Waters
Stars: Lindsay Lohan, Rachel McAdams, Tina Fey
Description: This teen comedy, written by Tina Fey, follows a girl who moves to a new high school and gets caught up in the popular clique. The film is known for its sharp wit and humorous take on high school politics.
Plot: Cady Heron navigates the social hierarchy of high school while dealing with the manipulative and glamorous Plastics.
Why should I watch it: The film is a hilarious and sharp satire of high school life, with memorable performances and quotable lines.
IMDb: 7.1
Rotten Tomatoes: 84%
Trailer: Mean Girls Trailer
4. To All the Boys I've Loved Before (2018)
Director: Susan Johnson
Stars: Lana Condor, Noah Centineo, Janel Parrish
Description: Based on Jenny Han's novel, this charming teen romance follows Lara Jean, whose secret love letters are accidentally sent to her crushes. It’s a delightful exploration of young love, with a modern twist.
Plot: Lara Jean’s secret love letters are accidentally mailed to her crushes, leading to unexpected romantic adventures.
Why should I watch it: The film is praised for its sweet story, engaging performances, and modern take on the classic teen romance.
IMDb: 7.1
Rotten Tomatoes: 96%
5. Easy A (2010)
Director: Will Gluck
Stars: Emma Stone, Penn Badgley, Amanda Bynes
Description: Inspired by "The Scarlet Letter," this comedy follows a high school student who uses the school’s rumor mill to advance her social standing. Olive Penderghast’s reputation is turned upside down when she pretends to have romantic encounters to help out her friends.
Plot: Olive Penderghast pretends to have romantic encounters to help her social standing, leading to unexpected consequences.
Why should I watch it: The film is sharp, witty, and features a breakout performance by Emma Stone.
IMDb: 7.0
Rotten Tomatoes: 85%
Trailer: Easy A Trailer
6. The Princess Diaries (2001)
Director: Garry Marshall
Stars: Anne Hathaway, Julie Andrews, Hector Elizondo
Description: This film follows a shy teenager who discovers she is the heir to the throne of a European kingdom. Mia Thermopolis must learn how to be a princess under the guidance of her grandmother while dealing with high school life.
Plot: Mia Thermopolis discovers she is a princess and must navigate the challenges of royalty and high school life.
Why should I watch it: The film is a delightful and heartwarming story with a breakout performance by Anne Hathaway.
IMDb: 6.4
Rotten Tomatoes: 48%
Trailer: The Princess Diaries Trailer
7. She's the Man (2006)
Director: Andy Fickman
Stars: Amanda Bynes, Channing Tatum, Laura Ramsey
Description: This modern adaptation of Shakespeare's "Twelfth Night" sees a teenage girl disguise herself as her brother to join a boys' soccer team. Viola Hastings pretends to be her twin brother, Sebastian, to prove she can play soccer just as well as the boys.
Plot: Viola disguises herself as her twin brother to join a boys' soccer team, leading to romantic and comedic complications.
Why should I watch it: The film is a hilarious and clever take on gender roles, with a standout comedic performance by Amanda Bynes.
IMDb: 6.3
Rotten Tomatoes: 43%
Trailer: She's the Man Trailer
8. A Cinderella Story (2004)
Director: Mark Rosman
Stars: Hilary Duff, Chad Michael Murray, Jennifer Coolidge
Description: A modern retelling of the Cinderella story set in a high school, where a shy teen's secret online relationship with a popular boy leads to real-life complications. Sam Montgomery must overcome her evil stepmother and stepsisters to attend the school dance and meet her online crush.
Plot: Sam Montgomery navigates high school and her evil stepmother while trying to meet her secret online crush at the school dance.
Why should I watch it: The film is a sweet and entertaining update of a classic fairy tale, with charming performances by the leads.
IMDb: 5.9
Rotten Tomatoes: 12%
Trailer: A Cinderella Story Trailer
9. The DUFF (2015)
Director: Ari Sandel
Stars: Mae Whitman, Robbie Amell, Bella Thorne
Description: This high school comedy follows a teenage girl who discovers she is the "Designated Ugly Fat Friend" and sets out to reinvent herself. Bianca enlists the help of a popular jock to transform her image and take down the school’s queen bee.
Plot: Bianca transforms her image with the help of a popular jock to confront the school's queen bee.
Why should I watch it: The film is funny, relatable, and features a standout performance by Mae Whitman.
IMDb: 6.4
Rotten Tomatoes: 73%
Trailer: The DUFF Trailer
10. The Spectacular Now (2013)
Director: James Ponsoldt
Stars: Miles Teller, Shailene Woodley, Brie Larson
Description: This coming-of-age romantic drama follows the relationship between a charming high school senior and an introverted girl. Sutter Keely, a popular party boy, forms an unexpected bond with the shy and diligent Aimee Finecky.
Plot: Sutter Keely and Aimee Finecky navigate their relationship amidst the challenges of teenage life.
Why should I watch it: The film is a poignant and realistic portrayal of teenage life and romance, with strong performances.
IMDb: 7.1
Rotten Tomatoes: 91%
Trailer: The Spectacular Now Trailer
11. Paper Towns (2015)
Director: Jake Schreier
Stars: Nat Wolff, Cara Delevingne, Austin Abrams
Description: Based on John Green's novel, this film follows a high school boy who embarks on a road trip to find his missing crush. Quentin Jacobsen and his friends go on a quest to find Margo Roth Spiegelman after she disappears, leaving behind clues.
Plot: Quentin and his friends embark on a road trip to find Margo, following the clues she left behind.
Why should I watch it: The film is a touching and thought-provoking coming-of-age story with a sense of adventure.
IMDb: 6.3
Rotten Tomatoes: 58%
Trailer: Paper Towns Trailer
12. Angus, Thongs and Perfect Snogging (2008)
Director: Gurinder Chadha
Stars: Georgia Groome, Aaron Taylor-Johnson, Karen Taylor
Description: Based on the novels by Louise Rennison, this British teen comedy follows the life of a 14-year-old girl as she navigates the ups and downs of teenage life. Georgia Nicholson deals with typical teenage dilemmas, including boys, friendships, and self-image.
Plot: Georgia Nicholson navigates the challenges of teenage life, including romance, friendships, and self-image.
Why should I watch it: The film is relatable and funny, capturing the awkwardness and excitement of being a teenager.
IMDb: 6.3
Rotten Tomatoes: 72%
13. Flipped (2010)
Director: Rob Reiner
Stars: Madeline Carroll, Callan McAuliffe, Rebecca De Mornay
Description: Based on the novel by Wendelin Van Draanen, this film follows two eighth-graders who have different feelings about each other over the years. Juli Baker has a crush on her neighbor Bryce Loski, who initially does not feel the same way, but their feelings flip as they grow up.
Plot: Juli and Bryce's feelings for each other evolve over the years as they navigate the complexities of young love.
Why should I watch it: The film is a charming and nostalgic look at young love, with a heartwarming story and strong performances.
IMDb: 7.7
Rotten Tomatoes: 54%
Trailer: Flipped Trailer
14. The Edge of Seventeen (2016)
Director: Kelly Fremon Craig
Stars: Hailee Steinfeld, Woody Harrelson, Kyra Sedgwick
Description: This coming-of-age comedy-drama follows a high school junior who struggles with the typical ups and downs of adolescence. Nadine Franklin navigates high school life, friendships, and family issues, finding solace in her unlikely friendship with her teacher.
Plot: Nadine Franklin deals with the challenges of high school, friendships, and family dynamics.
Why should I watch it: The film is a heartfelt and relatable portrayal of teenage life, with a standout performance by Hailee Steinfeld.
IMDb: 7.3
Rotten Tomatoes: 94%
Trailer: The Edge of Seventeen Trailer
15. The Sisterhood of the Traveling Pants (2005)
Director: Ken Kwapis
Stars: Amber Tamblyn, Alexis Bledel, America Ferrera
Description: Based on Ann Brashares' novel, this film follows four best friends who share a pair of jeans that fits each of them perfectly, despite their different body types. The girls embark on separate summer adventures, staying connected through letters and the magical pair of pants.
Plot: Four friends navigate separate summer adventures, connected by a pair of magical jeans.
Why should I watch it: The film is a touching and uplifting story about friendship and young love, with strong performances by the ensemble cast.
IMDb: 6.5
Rotten Tomatoes: 77%
16. The Perfect Date (2019)
Director: Chris Nelson
Stars: Noah Centineo, Laura Marano, Camila Mendes
Description: This Netflix original follows a high school student who creates an app to offer himself as a fake date to earn money for college. Brooks Rattigan pretends to be a variety of different boyfriends for different girls, but finds himself falling for the real girl next door.
Plot: Brooks Rattigan offers himself as a fake date through an app, but finds himself falling for a real girl.
Why should I watch it: The film is fun and charming with a charismatic performance by Noah Centineo.
IMDb: 5.8
Rotten Tomatoes: 65%
Trailer: The Perfect Date Trailer
17. The First Time (2012)
Director: Jonathan Kasdan
Stars: Dylan O'Brien, Britt Robertson, Victoria Justice
Description: This coming-of-age romantic comedy follows two high school students who meet at a party and develop a connection over one weekend. Dave and Aubrey's budding romance faces typical teenage challenges as they navigate their feelings for each other.
Plot: Dave and Aubrey navigate the complexities of young love over the course of a weekend.
Why should I watch it: The film is a sweet and genuine portrayal of young love, with strong chemistry between the leads.
IMDb: 6.8
Rotten Tomatoes: 47%
Trailer: The First Time Trailer
18. Starstruck (2010)
Director: Michael Grossman
Stars: Sterling Knight, Danielle Campbell, Maggie Castle
Description: This Disney Channel original movie follows a Midwestern girl who falls for a famous pop star while visiting Los Angeles. Jessica Olson and pop star Christopher Wilde navigate their budding romance amidst media frenzy and personal challenges.
Plot: Jessica Olson falls for pop star Christopher Wilde while visiting Los Angeles, leading to a whirlwind romance.
Why should I watch it: The film is a charming and sweet teen romance with catchy music and likable leads.
IMDb: 6.1
Rotten Tomatoes: N/A
Trailer: Starstruck Trailer
19. The Last Song (2010)
Director: Julie Anne Robinson
Stars: Miley Cyrus, Liam Hemsworth, Greg Kinnear
Description: Based on Nicholas Sparks' novel, this film follows a rebellious teenager who reconnects with her estranged father during a summer at the beach. Ronnie Miller finds love and family bonds while spending the summer with her father, dealing with her past and her feelings for a local boy.
Plot: Ronnie Miller reconnects with her estranged father during a summer at the beach, finding love and family bonds.
Why should I watch it: The film is a touching and emotional story about love, family, and forgiveness, with strong performances by the leads.
IMDb: 6.0
Rotten Tomatoes: 21%
Trailer: The Last Song Trailer
20. John Tucker Must Die (2006)
Director: Betty Thomas
Stars: Brittany Snow, Jesse Metcalfe, Ashanti
Description: This teen comedy follows three girls who team up to take revenge on the school’s biggest player, John Tucker. The girls enlist the help of a new student to break John Tucker’s heart by making him fall in love with her.
Plot: Three girls team up to break the heart of the school's biggest player, John Tucker, by making him fall for a new student.
Why should I watch it: The film is a fun and entertaining story about friendship and revenge, with a humorous and engaging plot.
IMDb: 5.7
Rotten Tomatoes: 27%
Trailer: John Tucker Must Die Trailer
21. Sierra Burgess Is a Loser (2018)
Director: Ian Samuels
Stars: Shannon Purser, Kristine Froseth, RJ Cyler
Description: A modern retelling of "Cyrano de Bergerac," this film follows a high school girl who teams up with a popular cheerleader to win the heart of her crush. Sierra Burgess catfishes her crush, Jamey, with the help of the school's queen bee, Veronica.
Plot: Sierra Burgess catfishes her crush, Jamey, with the help of the school's queen bee, Veronica, leading to unexpected consequences.
Why should I watch it: The film is a fresh and entertaining take on a classic story, with a strong performance by Shannon Purser.
IMDb: 5.8
Rotten Tomatoes: 61%
Trailer: Sierra Burgess Is a Loser Trailer
22. Ella Enchanted (2004)
Director: Tommy O'Haver
Stars: Anne Hathaway, Hugh Dancy, Cary Elwes
Description: This fantasy romantic comedy follows a young woman who is under a spell to obey every command she is given. Ella of Frell sets out on a quest to break her curse and discovers love and adventure along the way.
Plot: Ella of Frell embarks on a quest to break a spell that forces her to obey every command, finding love and adventure along the way.
Why should I watch it: The film is a fun and whimsical fairy tale with a charming performance by Anne Hathaway.
IMDb: 6.3
Rotten Tomatoes: 50%
Trailer: Ella Enchanted Trailer
23. The Lizzie McGuire Movie (2003)
Director: Jim Fall
Stars: Hilary Duff, Adam Lamberg, Yani Gellman
Description: This film follows the beloved Disney Channel character Lizzie McGuire as she travels to Rome and gets mistaken for a pop star. Lizzie McGuire embarks on a European adventure, discovering romance and her own potential along the way.
Plot: Lizzie McGuire travels to Rome and is mistaken for a pop star, leading to a European adventure filled with romance and self-discovery.
Why should I watch it: The film is a fun and nostalgic continuation of the popular TV series, with a delightful performance by Hilary Duff.
IMDb: 5.5
Rotten Tomatoes: 40%
Trailer: The Lizzie McGuire Movie Trailer
24. What a Girl Wants (2003)
Director: Dennie Gordon
Stars: Amanda Bynes, Colin Firth, Kelly Preston
Description: This comedy follows an American teenager who travels to London to find her aristocratic father and discover her roots. Daphne Reynolds meets her father, Lord Henry Dashwood, and tries to fit into his high society life while maintaining her unique personality.
Plot: Daphne Reynolds travels to London to meet her aristocratic father and navigate his high society life while staying true to herself.
Why should I watch it: The film is a lighthearted and charming story with a delightful performance by Amanda Bynes.
IMDb: 5.8
Rotten Tomatoes: 35%
Trailer: What a Girl Wants Trailer
25. Nick and Norah's Infinite Playlist (2008)
Director: Peter Sollett
Stars: Michael Cera, Kat Dennings, Aaron Yoo
Description: This romantic comedy follows two teenagers who spend an adventurous night in New York City searching for a secret concert. Nick and Norah, both nursing broken hearts, meet by chance and embark on a night of music and unexpected romance.
Plot: Nick and Norah meet by chance and spend an adventurous night in New York City searching for a secret concert.
Why should I watch it: The film is a charming and quirky romantic comedy with great chemistry between the leads and a fantastic soundtrack.
IMDb: 6.6
Rotten Tomatoes: 74%
26. Love, Rosie (2014)
Director: Christian Ditter
Stars: Lily Collins, Sam Claflin, Christian Cooke
Description: This romantic comedy follows the ups and downs of a lifelong friendship between Rosie and Alex, who have feelings for each other but keep missing their chances to be together. The film explores their complicated relationship over the years.
Plot: Rosie and Alex navigate their complicated friendship and romantic feelings over the years, often missing their chances to be together.
Why should I watch it: The film is a touching and relatable story about timing and the challenges of finding true love.
IMDb: 7.2
Rotten Tomatoes: 31%
Trailer: Love, Rosie Trailer
27. Letters to Juliet (2010)
Director: Gary Winick
Stars: Amanda Seyfried, Gael García Bernal, Vanessa Redgrave
Description: This romantic comedy follows an aspiring writer who finds an unanswered love letter in Verona and sets out to reunite the lovers. Sophie discovers romance and adventure in the process.
Plot: Sophie sets out to reunite a couple after finding an unanswered love letter in Verona, discovering romance and adventure along the way.
Why should I watch it: The film is a charming and heartwarming story about love and second chances, with beautiful Italian scenery.
IMDb: 6.5
Rotten Tomatoes: 41%
Trailer: Letters to Juliet Trailer
28. She's All That (1999)
Director: Robert Iscove
Stars: Freddie Prinze Jr., Rachael Leigh Cook, Matthew Lillard
Description: This teen romance follows a high school jock who makes a bet that he can turn an unattractive girl into the school's prom queen. Zack Siler transforms Laney Boggs into a prom queen contender, only to fall for her in the process.
Plot: Zack Siler transforms Laney Boggs into a prom queen contender as part of a bet, only to fall for her in the process.
Why should I watch it: The film is a quintessential 90s teen movie with a charming story and memorable moments.
IMDb: 5.9
Rotten Tomatoes: 41%
Trailer: She's All That Trailer
29. The Kissing Booth (2018)
Director: Vince Marcello
Stars: Joey King, Jacob Elordi, Joel Courtney
Description: This Netflix original follows a high school girl who falls for her best friend's older brother, breaking an important friendship rule. Elle Evans finds herself in a complicated situation when she starts a secret romance with her best friend's brother, Noah.
Plot: Elle Evans starts a secret romance with her best friend's brother, Noah, leading to complications.
Why should I watch it: The film is a fun and light-hearted teen romance with charming leads.
IMDb: 6.0
Rotten Tomatoes: 17%
Trailer: The Kissing Booth Trailer
30. The Fault in Our Stars (2014)
Director: Josh Boone
Stars: Shailene Woodley, Ansel Elgort, Nat Wolff
Description: Based on John Green's novel, this film tells the heart-wrenching love story of two teenagers with cancer. It explores themes of love, loss, and the fleeting nature of life.
Plot: Hazel and Gus, two teenagers with terminal illnesses, fall in love and embark on a journey to meet a reclusive author.
Why should I watch it: The film's emotional depth and strong performances have made it a favorite among audiences.
IMDb: 7.7
Rotten Tomatoes: 81%
Trailer: The Fault in Our Stars Trailer
These films have captivated audiences with their heartfelt stories, humor, and memorable moments, making them standout teen or tween comedic love stories from the past 25 years.
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