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A lot of nostalgic things came out of the 90s and 2000s. From hit music, questionable fashion sense, and even movies and television shows that are still a treat to watch. Teen romance movies from the 90s and 2000s had a certain charm that isn’t seen today on the big screen. Teen romance movies were a way to escape into a love story that seemed too good to be true, usually following a popular boy and a quiet nerdy girl who fall in love after a makeover or two. In other cases, they featured characters who were polar opposites who found their way into each other’s hearts.
Teen romance movies can be comedic high school adventures or dramas that tug at the heartstrings, but they always seem to play out like a modern fairy tale. It’s not every day that a teenage outsider learns they’re actually royalty or becomes embedded with the most popular kids in school, but teen rom-coms find a way to make the audience believe it. The 1990s and 2000s are two decades notorious for producing some of the most iconic teen romance movies. Many became instant classics and still hold up today.
20 Clueless (1995)
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Available to stream on Pluto TV and Paramount+
Clueless is a loose remake of a Jane Austen classic Emma and the classic story sees a popular, if shallow, protagonist, Cher (Alicia Silverstone), who means well but finds herself in a little trouble when she meddles in the love lives of her friends. Silverstone charmed audiences as Cher, and Brittany Murphy became iconic as Tai with her perfect line delivery. While some of the fashion might be dated now and some of the slang might not be used today, the movie is a great snapshot of 90s cinema for teens. Silverstone and Paul Rudd’s chemistry in the film was perfection among 90s teen romance movies.
19 Get Over It (2001)
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Available to stream on Starz
Kirsten Dunst, like Reese Witherspoon and Mandy Moore, found a niche in late-90s and early-2000s teen romance movies. She appeared in many of them, and though Get Over It made a smaller splash than other teen movies in the same era, it’s truly unique among the teen romances of the time.
In the film, Berke (Ben Foster) is desperately trying to get his ex-girlfriend back by joining his high school’s production of A Midsummer’s Night Dream alongside her and her new boyfriend. As romantic comedy rules dictate, however, he ends up falling for someone else in the process. With musical numbers and nearly all the teen rom-com tropes in one place, the movie is a fun ride still today.
18 Drive Me Crazy (1999)
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Available to stream on Cinemax
Reminiscent of the ’80s rom-com Can’t Buy Me Love, Drive Me Crazy features a popular girl (Melissa Joan Hart) and an outsider boy (Adrian Grenier) who strike up a deal to make their exes jealous. A makeover and a few misunderstandings later, they get their happy ending, just not in the way they expect. The movie came at the height of Melissa Joan Hart’s popularity as she’d already ridden the wave of Nickelodeon’s Clarissa Explains It All as a kid and Sabrina The Teenage Witch as a teen. The title also got a tie-in music video courtesy of Britney Spears, making it even more memorable for pop music fans.
17 Save The Last Dance (2001)
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Available to stream on Paramount+
If there’s one glaring fault in late-90s and early-2000s teen romance movies, it’s that the leads were very rarely people of color, or portrayed in interracial relationships. Most often, the actors of color in a teen rom-com were the best friends or the sidekicks. That wasn’t so for Save The Last Dance, though the movie is more dramatic than most upbeat 2000s teen romance movies.
The movie follows Sara (Julia Stiles), who’s trained in ballet, and Derek (Sean Patrick Thomas), who teaches her to loosen up with a little hip-hop. The duo has enough chemistry to carry the film themselves, but the movie is stacked with even more talent in the form of Kerry Washington and Bianca Lawson in supporting roles.
16 Bring It On (2000)
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Available to rent or purchase on Amazon Prime Video
While Bring It On is more remembered as a sports comedy than a 2000s teen romance movie, the main character of Torrance (Kirsten Dunst) does have a romantic storyline throughout the movie. She breaks up with her cheating college boyfriend and falls for her new friend’s brother, all while trying to reform her cheer squad which has unknowingly been using stolen cheers.
What’s really great about Bring It On is that, though Torrance gets her happy romantic ending, the movie doesn’t stick to the tropes the audience knows. Torrance’s team doesn’t win the big championship as there is a more deserving team in the Clovers. The movie also spawned a whole slew of direct-to-video sequels making cheerleading practically its own genre of teen movies.
15 How To Deal (2003)
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Available to rent or purchase on Amazon Prime Video
Mandy Moore was a teen romance movie icon during the 2000s. After the immense success of A Walk to Remember, she starred a year later in a movie titled How to Deal in 2003. The film follows Halley Martin (Moore), who no longer believes in a perfect love story. She becomes disillusioned after her parent’s divorce, her mother’s loneliness, her sister’s engagement, and the shallow lives of her teenage peers, but things take a turn when her best friend’s boyfriend suddenly dies of a heart attack while she’s pregnant. In the midst of it all, Halley starts to fall for the cool and edgy Macon Forrester (Trent Ford).
14 Keith (2008)
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Available to stream on Tubi, Amazon Prime Video, and The Roku Channel
Many teens who grew up during the 2000s had a crush on the pop sensation Jesse McCartney. In 2008, fans got to see the singer-songwriter in the lead role in Keith. The independent drama is a hidden gem when it comes to 2000s teen romance movies and follows Natalie (Elisabeth Harnois), who is academically perfect and has her future mapped out before becoming lab partners with Keith (McCartney) and getting whisked into a life of carefree decisions. However, while Keith and Natalie’s relationship starts to blossom, Keith is hiding a secret that could change everything, so it’s not as straightforward as a lot of other 2000s teen romance movies.
13 The Princess Diaries (2001)
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Available to stream on Disney+
The Princess Diaries is inarguably one of the most well-known teen movies created by Disney in the 2000s, and it skyrocketed Anne Hathaway to stardom. The movie brought to life every young kid’s dream of living a fairytale as main character Mia Thermopolis (Hathaway) isn’t the most popular girl in school but one day, she learns she is of royal lineage and must train to become a princess of Genovia. Her famous makeover catches the attention of her crush and everyone else, but with her new fame, she starts losing the people she cares for most.
12 First Daughter (2004)
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Available to stream on Hulu
First Daughter is all about Samantha MacKenzie (Katie Holmes) being fed up with her sheltered life as the president’s daughter. She finally gets a break when she’s allowed to attend college in California but under Secret Service protection. Her protective detail causes her trouble on many occasions, but Samantha soon meets James Lansome (Marc Blucas) and develops a close bond. James is the only one who helps Samantha feel normal for a change, but James isn’t just a simple resident advisor like Samantha thought, so there are some extra twists to the tale.
11 What A Girl Wants (2003)
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Available to rent or purchase on Amazon Prime Video
In the 2000s, Amanda Bynes had more than a handful of well-recognized guilty pleasure movies from Sydney White to She’s the Man. In 2003, she starred as Daphne in What a Girl Wants, and the movie’s storyline was a new type of princess story. Daphne grew up not knowing her father and on her sixteenth birthday makes the journey to England to find him. She learns her father is a top politician who left his carefree life behind and as Daphne tries to assimilate into her father’s life, she also falls in love with a musician.
10 Angus, Thongs And Perfect Snogging (2008)
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Available to stream on Pluto TV
Angus, Thongs and Perfect Snogging has a bit of everything for fans of 2000s teen romance movies from embarrassing comedy, and a quirky teen romance, to the qualms of trying to get through adolescence. The movie also helped to put Aaron Taylor-Johnson on the map as a heartthrob before he hit it big in Hollywood. Georgia (Georgia Groome) gets a major crush on a new student (Taylor-Johnson) and does everything possible to try and woo him. Georgia isn’t the most put-together teen and often embarrasses herself, all while worrying about her parent’s relationship and the not-so-great aspects of being a teen, so it’s packed with relatable moments.
9 Cruel Intentions (1999)
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Available to rent or purchase on Amazon Prime Video
Cruel Intentions is a cult classic teen romance movie from the 90s for those looking for a more twisted take on the tropes of the genre. It’s based on the novel Les Liaisons Dangereuses by Pierre Choderlos de Laclos and the story is much darker and more mature in its themes than most teen romance movies. It follows a privileged teen named Sebastian (Ryan Phillippe), who thinks he has it all and is untouchable, especially when it comes to his various escapades. His stepsister Kathryn (Sarah Michelle Gellar) agrees to a wager on seducing Annette Hargrove (Reese Witherspoon), the virgin daughter of the new headmaster, but his feelings get complicated.
8 The Prince & Me (2004)
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Available to stream on Pluto TV and Paramount+
The Prince & Me became a well-known romance movie in 2008 because it brought to life a classic fairytale story when a normal country girl finds a royal prince to fall in love with. Prince Edvard (Luke Mably) lives his life as a playboy and refuses to accept the responsibilities of his title, and he ventures to America to experience the fun college life. He makes an impression on his lab partner, Paige (Julia Stiles) and despite trying to evade emotions, they fall in love. There’s one problem, she doesn’t know who he really is.
7 Romeo + Juliet (1996)
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Available to stream on HBO Max
The famed love story of Romeo and Juliet has been retold and adapted many times on screen. The Shakespeare play got a revamp in 1996 with a modern twist. The movie follows the same basic storyline of two teens who fall in love despite being part of rival families. In this version, however, the rival families are rival gangs in the modern world. The film also adds more violence, drama, and even drug use. The ending is kept relatively the same with the vials of poison and fated death, but instead of a dagger, it’s a gun. The classic story loses none of its power in the adaptation though.
6 A Cinderella Story (2004)
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Available to rent or purchase on Amazon Prime Video
Many who grew up in the 90s and 2000s have fond memories of the movie A Cinderella Story starring Hilary Duff and Chad Michael Murray. It was a teen romance staple that modernized the popular Cinderella story. Not to mention, Chad Michael Murray was established as a teen heartthrob during the time thanks to One Tree Hill.
The story follows Sam (Duff), who’s a waitress in her father’s diner run by her cruel stepmother after his passing. After developing a friendship with a pen pal named “Nomad,” they decide to meet at the Halloween dance. Dressed in a white ball gown and mask, Sam discovers her “Nomad” to be the school’s popular football player. Unable to reveal her identity, she flees at midnight leaving behind her cell phone and leaving her Prince to go on the hunt to uncover who she is.
5 Never Been Kissed (1999)
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Available to stream on Hulu, Amazon Prime Video, and Disney+
Never Been Kissed is a 1999 romantic comedy that isn’t necessarily a film about teenage love, but it is disguised as one. Josie Geller (Drew Barrymore), a copywriter, is tasked with posing as a high school student to research teen culture. She manages to fool everyone and gets her shot at redemption for her failed teenage years, but she doesn’t expect to fall in love with her handsome English teacher. It all leads to a crowd-pleasing finish, cementing it as one of the top 90s movies about teenage romance, even if the characters in love are a little older when they find it.
4 Twilight (2008)
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Available to stream on Showtime and Paramount+
Twilight defined a time in the early 2000s when all everyone could think about was vampires, werewolves, and romance. It was the gateway for following popular book series, television shows, and movies around the genre. Twilight wasn’t quite like any other supernatural teen romance seen before, following a seemingly ordinary girl named Bella (Kristen Stewart) who has her life changed when she meets Edward Cullen (Robert Pattinson). She’s whisked into a dangerous and epic love story as Edward and his family are vampires, and her closest friend is part of a werewolf tribe. It’s relatively action-packed for a 2000s teen romance movie, but still all about the character’s tangled affections.
3 She’s All That (1999)
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Available to stream on HBO Max
She’s All That is a teen romance movie that some might not have realized is a modern adaptation of My Fair Lady. It became one of the most popular teen films of the late 90s and still holds up today. Zackary (Freddie Pricne Jr.) is the big shot on campus with friends, a popular girlfriend, and golden opportunities until his girlfriend dumps him after meeting a celebrity during spring break. Now having his reputation and ego deflated, he makes a bet with his friend that he can turn any girl into prom queen material in six weeks. The target? The dorky, unpopular art girl, Laney Boggs (Rachael Leigh Cook).
2 A Walk To Remember (2002)
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Available to stream on Tubi
Based on Nicholas Spark’s book, A Walk To Remember became a coming-of-age teen movie with long-lasting appeal. The film follows Landon Carter (Shane West), who has no direction for his future after falling into some trouble. He’s forced to take part in service duties and one of them is taking part in the school play. Having difficulties, he seeks the help of the minister’s daughter, and an improbable romance blossoms.
1 10 Things I Hate About You (1999)
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Available to stream on Disney+
10 Things I Hate About You was adapted from the Shakespeare play The Taming of the Shrew but placed in a modern setting and became a teen classic. It was a box office hit and which gave breakthrough movie roles to Julia Stiles, Heath Ledger, and Joseph Gordon-Levitt.
The movie follows a new student named Cameron (Gordon-Levitt), who becomes smitten with a girl. The problem is she’s not allowed to date until her ill-tempered older sister does so first s he gets an affluent senior to convince bad boy Patrick Verona (Ledger) to get Kat (Stiles) on a date. Originally doing so for money, Patrick realizes that Kat is so much more than he thought, all leading to one teen romance movie history’s most famous confessions of love.
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