Summary

  • Teen romance movies from the ’90s and 2000s had a certain charm, often depicting love stories that seemed too good to be true, featuring popular boys and quiet nerdy girls or polar opposites finding their way into each other’s hearts.
  • These movies often played out like modern fairy tales, with comedic high school adventures or heartstring-tugging dramas, making the audience believe in unlikely scenarios like a teenage outsider discovering they’re royalty or becoming embedded with the popular kids in school.
  • The iconic teen romance movies from the ’90s and 2000s still hold up today, offering a mix of romance, comedy, and friendship. They provide an escape into a world of love and friendship while capturing the adolescent experience of being an outsider or pursuing dreams against all odds.

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A lot of nostalgic things came out of the 90s and 2000s including some great ’90s movies about teenage romance. There might be questionable fashion, but there is also great music and tropes that are still used in teen movies today. Teen romance movies from the 90s and 2000s had a certain charm. 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.

25 John Tucker Must Die (2006)

Brittany Snow faces off against Ashanti, Sophia Bush, and Arielle Kebbel in John Tucker Must Die

  • Available to stream on Prime Video

Teen romance movies that involve revenge plots usually employ the fake dating trope to make another character (or more than one) jealous. That’s not the case with John Tucker Must Die. Instead, a group of teenage girls team up to break the heart of a teenage boy.

Ashanti, Arielle Kebbel, and Sophia Bush play three very different high school teenagers who have all dated the same boy in the past. In fact, they all dated him at the same time without knowing. When they discover his deception, they turn on one another, but Brittany Snow is the new girl in school who convinces them that they should team up instead. The four new allies turn her into John Tucker’s (Jesse Metcalfe) perfect girl so that she can break his heart, but their scheme works a little too well. The movie is as much a romance as it is about the bonds of female friendship, and it’s definitely a fun ride to get to the predictable ending.

RELATED: Coming-Of-Age Movie That Define Millenials

24 Angus (1995)

Angus talking to his crush outside the school dance in the 1995 movie Angus

  • Available to rent on Apple TV, Vudu, and Google Play

A freshman in high school, Angus (Charlie Talbert) has been bullied all his life, usually about being overweight. When he decides he’s had enough, he applies to transfer to a better school where he thinks he can get away from his bullies and his problems. Before he transfers though, his friend rigs a school election that gets him the spot of King at a freshman dance, and his crush as the Queen, hoping to give him a nice send-off.

Rigging the votes causes more problems for Angus since he can’t dance and he and his friend are only targeted even more by the bullies. With some sage advice from his grandfather though, and a few touching moments with his crush, Angus learns to stand up to his bullies and be honest about his feelings. The ’90s teen romance movie features a lot of the teen movie tropes that are prevalent today, but it’s still a sweet story that captures the adolescent experience of being an outsider. It’s also James Van der Beek’s first film role – as the bully.

23 Bend It Like Beckham (2002)

Juliette, Jess, and their coach on the field in Bend It Like Beckham

  • Available to stream on Disney+

Before Keira Knightley became a star in the Pirates of the Caribbean franchise and before Parminder Nagra became a TV mainstay in ER and DI Ray, they were teenagers who just wanted to play their favorite sport in Bend It Like Beckham. The two played young women whose families didn’t want them to play football, but they found ways to be on the same team and pursue their dreams of playing professionally.

The characters fell for their coach, played by Jonathan Rhys Meyers, but a subplot in the movie featured one of their mothers believing the girls were hiding a lesbian relationship. Some viewers would have rather that been the romantic storyline of the movie. As it is, the two women have to reconcile the bumps in their friendship when they both want to pursue their dreams and support one another, but both have feelings for their coach. Bend It Like Beckham is even more about friendship than it is teen romance.

22 Edge Of Seventeen (1998)

A teenage boy in a record store in the 1998 movie Edge of Seventeen

  • Available to stream on Kanopy

Careful not to confuse this dramedy with the 2016 Hailee Steinfeld movie The Edge of Seventeen. Both movies feature teenagers coming of age as they pursue romantic relationships, but that is mostly where their similarities end. Edge of Seventeen is set in the 1980s and follows Eric Hunter (Chris Stafford) as he slowly comes to terms with his own sexuality.

Though he gradually comes to accept that he is gay after discovering a local club and working for a lesbian who encourages him to be true to himself, Eric has a harder time admitting the truth to his best friend (who has been harboring feelings for him and thinks he’s been playing with her feelings) and his mother. A string of hookups with other men leaves Eric looking for a substantial relationship and a place where he can really be himself.

21 Step Up (2006)

Jenna Dewan and Channing Tatum dancing together in the cropped poster for Step Up

  • Available to rent on Apple TV, Vudu, and Google Play

Dance movies became very popular in the early 2000s, and part of that was a result of the popularity of Step Up. Jenna Dewan and Channing Tatum starred as teens from two very different backgrounds who shared a love for dance. While she’s a modern dance student at a prestigious academy, he’s working as a janitor to fulfill community service hours after getting into trouble.

The two have different styles that they have to blend for a showcase that helps to determine both of their dancing futures and of course, they fall in love along the way. The soundtrack is great and the Step Up dance routines are beautiful to watch. Step Up spawned its own franchise, which is rare in the world of teen romance movies. It has four US sequels, a spinoff in China, a live show in India, and a streaming series on YouTube.

20 Clueless (1995)

Stacey Dash, Alicia Silverstone and Brittany Murphy in Clueless poster

  • 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 movies that include teenage romance.

RELATED: Best Makeover Movies Like Clueless

19 Get Over It (2001)

Berke and Kelly on stage in Get Over It

  • Available to stream on DirecTV

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)

Nicole lays on her bed with her head propped up by one hand in Drive Me Crazy

  • Available to stream on MAX

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 ’90s teen romance movie made great use of teen comedy tropes.

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)

A couple stand on a dance floor from Save the Last Dance

  • 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)

A split image depicts Cliff, Torrance, and Isis in Bring It On

  • Available to rent on Amazon Prime Video and AppleTV

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.

RELATED: 10 Ways That Bring It On Holds Up Today

15 How To Deal (2003)

Mandy Moore and Trent Ford in How To Deal

  • Available to rent on Amazon Prime Video and AppleTV

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 movie is a blend of the stories of two Sarah Dessen novels: That Summer and Someone Like You.

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)

Keith and Natalie as school lab partners in Keith

  • Available to stream on Tubi 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)

Anne Hathaway in The Princess Diaries

  • 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 the royal 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)

Katie Holmes and Michael Keaton in First Daughter.

  • Available to stream on Plex

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)

Amanda Bynes in What a Girl Wants

  • 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. The movie got a lot of comparisons to The Princess Diaries when it was released, but both can be enjoyed on the merits of their differences as much as their similarities.

10 Angus, Thongs And Perfect Snogging (2008)

The main characters from Angus, Things and Perfect Snogging embrace

  • Available to stream on Hoopla

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)

Sebastian kissing Annette's cheek in Cruel Intentions

  • Available to rent or purchase on Amazon Prime Video

Cruel Intentions is a cult classic teen romance movie from the ’90s, but definitely not the typical ’90s movie featuring teenage romance. It’s 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.

RELATED: 10 Most Shocking Scenes In Cruel Intentions, Ranked

8 The Prince & Me (2004)

Luke Mably and Julia Stiles in The Prince & Me movie

  • Available to stream on MAX

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. It’s the kind of story that has inspired many modern Hallmark movies.

7 Romeo + Juliet (1996)

Leonardo Dicaprio and Claire Danes in Romeo and Juliet

  • Available to stream on Fubo

The famed love story of Romeo and Juliet has been retold and adapted many times on screen. The Shakespeare play got a revamp with a modern twist as a ’90s movie of teenage romance. 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, and the performances of the cast are outstanding.

6 A Cinderella Story (2004)

Sam and Austin dancing together in A Cinderella Story

  • Available to rent on Amazon Prime Video and AppleTV

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.

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