30 Unforgettable Teen Romance Movies from the 90s and 2000s

Stories of young love have always captured the attention of moviegoers and the 1990s and 2000s saw a lot of teen romance movies add to the genre. Although not every teen movie of this era has aged well, Many of them remain watch-worthy for more than just nostalgia. Whether it’s the beautifully executed tropes of friends-to-lovers, enemies-to-lovers, miscommunications, nerds and jocks falling in love, or just some classic teen coming-of-age stories, these remain absolute classics.

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 gets embedded with the most popular kids at 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.

30

But I’m a Cheerleader (1999)

A teen finds her sexuality at a conversion therapy camp

While The 90s are starting to see a few more LGBTQ+ stories represented in moviesIt is still rare to have such relationships explored in a teen romance movie. however, But I’m a cheerleader Taking a bold step in addressing these types of romance while also being a funny satire of the anti-gay community.

Natasha Lyonne stars in the movie as Megan, A popular high school cheerleader whose parents suspect she is gay And send her to a camp designed to “convert” gay teens. The movie is a hilarious and elevated comedy that is Pointed to the idea that such a lifestyle can and should be “cured.”

This is especially funny because the camp gives Megan a chance to really explore her feelings with another camp member, Graham (Clea DuVall). Their defiant yet intimate romance that forms allows them both to be free in ways they never could and to discover themselves.

29

American Pie (1999)

Four friends try to lose their virginity before high school ends

American pie Is often Seen as the beginning of the rough-out teen comedy phase. While that may be true, that doesn’t mean there isn’t also room for some romance in between all the crude jokes. The movie follows four male friends who make a pact to have sex before the end of their senior year of high school.

However, each of them encounters more than a few obstacles on the way. American pie Deals with several different romances during the movie. Ox (Chris Klein), the popular jock, finds himself falling for student Heather (Mena Suvari).

Meanwhile, high school sweethearts Kevin (Thomas Ian Nicholas) and Vicky (Tara Reid) deal with the thought of their romance coming to an end as they go their separate ways after high school. Although not the deepest of romances, the movie deals with teen relationships in a relatable way. While the American pie Movies continued with several sequels and spinoffs, none of them topped the humor and heart of the original.

28

Can’t Hardly Wait (1998)

An outsider tries to woo a popular girl at a high school party

Can hardly wait is another teen comedy that features some memorable romance alongside juvenile humor. The movie centers around Various characters come together in an epic high school party. At the center of the story is Preston (Ethan Embry), an outsider in his school who decides to attend the party with the sole intention of declaring his love for the popular girl, Amanda (Jennifer Love Hewitt), whom he has long Admired from afar. .

Can hardly wait is inspired by the movies of John Hughes and the teen romance of the 1980s, Effectively recovered that vibe. The central story of ​​the unpopular kid trying to get his shot at a girl out of his league is a well-known one used in many 80s and 90s rom-coms, but Can hardly wait Manages to make it charming, thanks largely to its likable cast.

27

Y Tu Mama También (2001)

Two best friends and an elderly woman set out on a road trip

While fans could not expect these Oscar-winning filmmaker behind Children of men And Gravity To have delivered one of the best teenage romances of the 2000s, Alfonso Cuarón found his own beautiful way to elevate the genre.

You mother Tombie is a Mexican coming-of-age story starring Gael García Bernal and Diego Luna as Two best friends who go on a road trip with a woman in her 20s, both of them develop feelings for the older and charismatic woman. The movie is funny, sexy and insightful with Cuarón’s beautiful directing and writing only making the intimate story all the more compelling.

The romance at the center of the movie is surprising with some turns that the audience may not see coming. However, it is also a bittersweet story of young friendship with the inevitability of the two young people from different backgrounds, which make their time together and the changes their relationship makes more exciting.

26

The Girl Next Door (2004)

A student teen falls for a porn star

Another movie inspired by a classic 80s romance, The girl next door is a raunchy reimagining of the Tom Cruise breakout teen movie Risky business. In this version, Emile Hirsch stars Matthew, an ambitious high school senior, has a crush on his attractive next-door neighbor, Danielle (Elisha Cuthbert), only to find out she is a porn star.

This sends him on an adventure in which he breaks out of his shell and lives more rebelliously thanks to Danielle. The movie received mixed reviews and poor box office upon its release but became a cult favorite years later. There is a lot of charm to this movie thanks to The romance that blossoms between the two leads.

While Matthew is made to be more adventurous, He also helps Danielle feel accepted in a world that judges her for her work. The movie also features a strong supporting cast that includes Paul Dano, Olivia Wilde and Timothy Olyphant in a scene-stealing villain role.

25

John Tucker Must Die (2006)

Four girls team up to bring down their ex

Teen romance movies that involve revenge plots usually use 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 who dated them all at the same time Without them knowing.

When they discover his deception, they decide to get back at him with the help of the new girl at school who will serve as his latest girlfriend. There aren’t too many rom-coms from that era that focus on female friendship Which is part of the reasons John Tucker must die stands out.

While the girls initially see each other as enemies, watching their bond gradually grow is entertaining and touching. Although the ending is predictable, there’s enough fun chemistry between the actors and a fun bit of dark humor to make it a solid coming-of-age movie aimed at millennials.

24

Angus (1995)

A bullied child gets a chance to impress his crush

Bullies are a common theme in teen movies of this era and the titular character in Angus Must contend with his share of cruel classmates. A freshman in high school, Angus (Charlie Talbert) has been bullied all his life. However, when his friend rigs the school votes for class president so Angus wins, He has the opportunity to dance with his crush and must learn how before the big dance.

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. Angus makes for an endearing hero worth cheering for. It also features the first movie role for James Van der Beek, who went from playing the bully in the movie to being a teen romance idol himself.

23

Bend It Like Beckham (2002)

Two young girls go for their dreams of playing soccer

Before Keira Knightley became a star in the Pirates of the Caribbean franchise and before Parminder Nagra became a television mainstay in He And DI RayThey are teenagers who just wanted to play their favorite sport in Bend it like Beckham.

The two play young women whose families didn’t want them to play football, but they found ways to be on the same team and follow their dreams of playing professionally while falling for their coach, played by Jonathan Rhys Meyers.

Along with being a rare and excellent soccer movie, Bend it like Beckham Stands apart from other teen romances of the era. Instead of the romance being the main focus, this is really a story about two young women pursuing a goal that everyone else is telling them is not realistic. It makes for A much-loved sports movie about determined young girls who can inspire many others.

22

Edge Of Seventeen (1998)

A young boy struggles with his sexuality in the 1980s

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

Although He gradually accepts 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 hard time admitting the truth to his best friend (who has horrible feelings for him and thinks he was playing with her feelings) and his mother.

The 90s proved that there was still a long way to go with gay representation on screen, however The Edge of Seventeen is a touching and thoughtful gay coming-of-age story That after resonances.

21

Step Up (2006)

A boy and girl from different backgrounds form a bond as dancing partners

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 star as teenagers from two very different backgrounds who share a love for dance. While she is a modern dance student at a prestigious academy, he works 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 determine both 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 it. Sequels, a spinoff in China, a live show in India and a streaming series on YouTube.

20

Clueless (1995)

A rich teen plays a match in her high school

Clueless is a loose adaptation of the Jane Austen classic Emma And the classic story sees a popular, shallow, yet kind-hearted protagonist, Cher (Alicia Silverstone), who means well but finds herself in a bit of trouble when she meddles in the love lives of her friends. However, while trying to find the perfect match for everyone else, Cher begins to think about her own romantic future.

Silverstone and Paul Rudd’s chemistry in this film is perfection among ’90s movies that include teenage romance.

Silverstone charmed audiences as Cher, being sweet and hilarious. Brittany Murphy also became iconic as Tye with her perfect line delivery. Although some of the fashion may be dated now and some of the slang may not be used today, This movie is a great snapshot of 90s cinema for teens. Silverstone and Paul Rudd’s chemistry in this film is perfection among ’90s movies that include teenage romance.

19

Get Over It (2001)

A young man tries to win back his girlfriend

Kirsten Dunst, like Reese Witherspoon and Mandy Moore, found a niche in late 90s and early 2000s teenage romance movies. She appeared in many of them, and though Get over it Made a smaller splash than other teen movies of the same era, It is truly unique among the teen romances of the time.

in this film, Berke (Ben Foster) is desperately trying to get his ex-girlfriend back By joining his high school’s production of A midnight dream Along with 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 almost all the teen rom-com tropes in one place, the movie is a fun ride. Ben Foster makes for a fun and unexpected rom-com lead with a nervous comedic energy that fits the role very well while Dunst is as charming as ever. It’s a reminder that sometimes teen romances from this era could work based on likable casting alone.

18

Drive Me Crazy (1999)

A girl and boy use each other to make their exes jealous

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 make 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, because she had already ridden the wave of Nickelodeon. Clarissa explains it all as a child and Sabrina the teenage witch like a teen

The title also got a tie-in music video courtesy of Britney SpearsMaking it even more memorable for pop music fans. The movie stuck with fans for being willing to be a little different and quirkier than the average rom-com of the time.

17

Save the Last Dance (2001)

A ballet dancer bonds with a hip-hop dancer

If there’s one glaring fault in late ’90s and early 2000s teen romance movies, it’s that The leads are very rarely people of color, or portrayed in interracial relationships. Most often, the actors of color in a teen rom-com are the best friends or the psychics.

This is not the case Save the last danceAlthough the movie is more dramatic than most upcoming 2000s teen romance movies. Another dance-centric movie, The Teen Romance follows Sara (Julia Stiles), who is 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 itself, but the movie is stacked with even more talent In the form of Kerry Washington and Bianca Lawson in supporting roles. The movie has a lasting legacy as Julia Stiles recently appeared on Saturday Night Live To spoof a scene from the movie.

16

Bring It On (2000)

The head of a cheer squad competes in the Championship

Bring it on Can be remembered as a sports comedy as much as a 2000s teen romance movie, but the main character of Torrance (Kirsten Dunst) has a romantic storyline throughout the movie. She breaks up with her cheating college boyfriend and falls for her new friend’s brotherAll while trying to reform her cheer squad that has unknowingly used stolen cheers.

What’s really great about it 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 because there is a more deserving team in the Clovers. The cheerleader culture also makes for a fun and unique world to explore. The movie also spawned a whole slew of direct-to-video sequels that make cheerleading practically its own genre of teen movies.

15

How to Deal (2003)

A young woman is disillusioned about love until she meets an intriguing new love interest

Mandy Moore was a teen romance movie icon in the 2000s. After the tremendous success of A walk to rememberShe starred a year later in a lesser known but still popular movie with the title How to act in 2003. The movie is a combination of the stories of two Sarah Dessen novels: That summer And Someone like you.

The film follows Holly Martin (Moore), who no longer believes in a perfect love story. She becomes disillusioned after her father’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 is pregnant.

In the midst of it all, Holly starts to fall for the cool and edgy Macon Forrester (Trent Ford). The movie is able to Balance its comedy and dramatic aspects with more confidence than many movies in the genreGive it a more unique vibe.

14

Keith (2008)

A gifted student falls for a carefree classmate

The pop sensation Jesse McCartney was a young star of the era Who is mostly known for his popular singing career but also made the transition to acting at the height of his popularity. In 2008, fans got to see the singer-songwriter in the main role in Keith.

A hidden gem when it comes to 2000s teen romance movies, this independent drama follows Natalie (Elisabeth Harnois), who excels academically and has her future mapped out before becoming lab partners with Keith (McCartney) and getting whisked. In a life of carelessness. Decisions.

However, while Keith and Natalie’s relationship starts to blossom, Keith is hiding a secret that could change everything. Not a straightforward romance movie, Keith likes to challenge some of the genre’s conventions in a look at how the importance of school work and life after high school can be measured against a teen romantic fling.

13

The Princess Diaries (2001)

Anne Hathaway stars as a teammate who discovers she is royalty

The movie brings to life the childhood dream of living a fairy tale.

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 brings to life the childhood dream of living a fairy tale.

Mia Thermopolis (Hathaway) is not the most popular girl at school, but one day, she learns that 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 to lose the people she cares about the most.

Mia’s story is based on Meg Cabot’s books.

The fairy tale element of this movie makes it a magical yet grounded movie. Anne Hathaway’s performance in this movie is a big reason the movie works so well How she makes the audience believe in this grounded and charming young woman’s transformation into graceful royalty while also maintaining her down-to-earth personality.

12

First Daughter (2004)

The daughter of the American president tries to find love

First daughter is all about Samantha MacKenzie (Katie Holmes) is fed up with her sheltered life as the president’s daughter. She finally gets a break when she is allowed to attend college in California but under Secret Service protection.

Her protective detail gets her into 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 is not just a simple resident advisor as Samantha thought, so there are some extra twists to the tale.

It’s a fun setting for the teen rom-com, take a look at The stressful life of growing up in the public eye and under extraordinary circumstances. Although the movie wasn’t a critical hit by any means, it had some great talent involved, including Michael Keaton as the president and Oscar winner Forest Whittaker as the movie’s director.

11

What a Girl Wants (2003)

A girl travels to England to meet the father she never knew

In the 2000s, Amanda Bynes had more than a handful of well-recognized guilty pleasure movies from Sidney White to She is the man. In 2003, she starred as Daphne in what a girl wants And the storyline of this movie was a new type of princess story.

Daphne grew up not knowing her father and on her sixteenth birthday made the trip to England to find him. She learns that her father is a top politician who has 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 is released, however, both can be enjoyed on the merits of their differences as much as their similarities. Bynes is a natural comedic talent and she puts those skills to good use In this delightful mix of teen romance and fish-out-of-water comedy.