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. While not every teen movie from this time period aged well, many of them remain watch-worthy for more than just nostalgia. Whether it is 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 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.

30 But I’m A Cheerleader (1999)

A Teen Finds Her Sexuality At A Conversion Therapy Camp

But I'm a Cheerleader - Poster - Natasha Lyonne

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But I'm A Cheerleader
Release Date
September 12, 1999
Runtime
85 Minutes
Director
Jamie Babbit
  • Headshot Of Natasha Lyonne
    Natasha Lyonne
    Megan
  • Headshot Of Clea DuVall
    Clea DuVall
    Graham

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But I'm a Cheerleader follows Megan, an all-American high school cheerleader, who is sent to a conversion therapy camp by her conservative parents after they suspect her of being a lesbian. The film explores her experiences at the camp as she navigates her identity and relationships.

While the 90s were starting to see a little more LGBTQ+ stories being represented in movies, it was still rare to have such relationships explored in a teen romance movie. However, But I’m a Cheerleader took a bold step in addressing these types of romances 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 that she is gay and send her to a camp that is designed to “convert” gay teens. The movie is a hilarious and elevated comedy that is poking fun at the idea that such a lifestyle can and needs to be “cured.”

It is especially funny as the camp gives Megan an opportunity 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

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American Pie
Release Date
July 9, 1999
Runtime
95 minutes
Director
Paul Weitz, Chris Weitz
  • Headshot Of Jason Biggs
    Jason Biggs
  • Headshot Of Chris Klein
    Chris Klein

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American Pie is a raucous teen comedy and the film that launched a revival of the genre. It follows a group of high school friends determined to lose their virginity before graduation and delves into the misadventures of the four boys as they navigate the complexities of relationships, peer pressure, and parental mishaps. You'll never look at warm apple pie the same again.

American Pie is often looked at as the beginning of the gross-out teen comedy phase. While that might be true, that doesn’t mean there is not also room for some romance amid all the dirty jokes. The movie follows four male friends who make a pact to have sex before the end of their high school senior year.

However, each of them encounters more than a few obstacles along the way. American Pie deals with several different romances over the course of the movie. Ox (Chris Klein), the popular jock, finds himself falling for studious Heather (Mena Suvari).

There have been nine American Pie movies to date.

Meanwhile, high school sweethearts Kevin (Thomas Ian Nicholas) and Vicky (Tara Reid) deal with the idea of their romance coming to an end as they go their separate ways after high school. While 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)

Cant Hardly Wait Movie Poster

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Can't Hardly Wait
Release Date
June 12, 1998
Runtime
101 Minutes
Director
Deborah Kaplan, Harry Elfont
  • Headshot of Ethan Embry
    Ethan Embry
  • Cast Placeholder Image
    Charlie Korsmo

WHERE TO WATCH

Streaming

School is finally over, and a diverse group of graduating seniors—from athletes and popular students to the academically inclined—converges at a rich classmate's house for a celebration. At the party, artistic Preston (Ethan Embry) aims to confess his long-held feelings to Amanda (Jennifer Love Hewitt), the school's most ired beauty. Meanwhile, geeky William (Charlie Korsmo) plots revenge against jock Mike (Peter Facinelli) for years of torment. In another twist, aspiring rapper Kenny (Seth Green) finds himself accidentally trapped in a room with the sarcastic Denise (Lauren Ambrose).

Can’t Hardly Wait is another teen comedy that features some memorable romances alongside juvenile humor. The movie centers around various characters coming together at 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 professing his love for the popular girl, Amanda (Jennifer Love Hewitt), who he’s long ired from afar.

Can't Hardly Wait is inspired by the movies of John Hughes and the teen romances of the 1980s, effectively recapturing that vibe. The central story of the unpopular kid trying to get his shot at a girl who is out of his league is a well-known one used in many rom-coms of the 80s and 90s, but Can’t Hardly Wait manages to make it charming, thanks largely to its likable cast.

27 Y Tu Mamá También (2001)

Two Best Friends And An Older Woman Set Out On A Road Trip

Y tu mamá también Film Poster

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Y Tu Mamá También
Not Rated
Drama
Release Date
June 8, 2001
Runtime
106 Minutes
Director
Alfonso Cuarón
  • Headshot of Maribel Verdú
    Maribel Verdú
  • Headshot Of Gael García Bernal
    Gael García Bernal

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Julio and Tenoch are two teenagers who, together with Luisa, an older woman, embark on a journey to a paradise beach. On a road trip through Mexico, the three end up getting involved and learning a lot about themselves and their relationships.

While fans might not expect the Oscar-winning filmmaker behind Children of Men and Gravity to have delivered one of the best teen romances of the 2000s, Alfonso Cuarón found his own beautiful way of elevating the genre.

Y tu mamá también is a Mexican coming-of-age story starring Gael García Bernal and Diego Luna as two best friends who set out on a road trip with a woman in her 20s, both of them developing 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 it taking some turns that audiences might not see coming. However, it is also a bittersweet story of young friendship with there being an inevitability of these two young men from different backgrounds drifting apart, which makes their time together and the changes their relationship takes all the more exciting.

Related
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There have been a plethora of successful female directors who have made a name for themselves with teen movies.

26 The Girl Next Door (2004)

A Studious Teen Falls For A Porn Star

The Girl Next Door

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The Girl Next Door
R
Release Date
April 9, 2004
Runtime
1h 49m
  • Headshot Of Elisha Cuthbert
    Elisha Cuthbert
  • Headshot Of Emile Hirsch
    Emile Hirsch

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Streaming
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The Girl Next Door (2004) is a coming-of-age romantic comedy directed by Luke Greenfield. The film stars Emile Hirsch as Matthew Kidman, a high school senior who falls for his new neighbor Danielle, played by Elisha Cuthbert. Their budding relationship takes a turn when Matthew discovers Danielle's past as a porn star, leading to a series of comical and poignant events that challenge his understanding of love and life.

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 who forms a crush on his attractive next-door neighbor, Danielle (Elisha Cuthbert), only to find out that 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 the 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 ing cast that includes Paul Dano, Olivia Wilde, and Timothy Olyphant in a scene-stealing villainous role.

25 John Tucker Must Die (2006)

Four Girls Team Up To Bring Down Their Ex

John Tucker Must Die (2006)

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John Tucker Must Die
Release Date
July 28, 2006
Runtime
89 minutes
Director
Betty Thomas
  • Headshot Of Jesse Metcalfe
    Jesse Metcalfe
  • Headshot Of Brittany Snow
    Brittany Snow

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John Tucker Must Die is a teen comedy film directed by Betty Thomas. The story follows three high school girls who learn they have been dating the same guy, John Tucker, and team up with a new girl to exact revenge. Their elaborate plan to bring him down takes unexpected turns, leading to humorous and insightful moments about relationships, popularity, and self-identity. The film stars Jesse Metcalfe, Brittany Snow, and Ashanti.

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 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 in school who will serve as his latest girlfriend. There are not too many rom-coms of the 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. While the ending is predictable, there is enough fun chemistry among the actors and a fun bit of dark humor to make it a solid coming-of-age movie aimed at millennials.

Related
13 Coming-Of-Age Movies That Define Millennials

The 90s and 00s were the best eras for coming-of-age movies, and there are plenty of iconic movies that really captured growing up as a millennial.

24 Angus (1995)

A Bullied Kid Gets A Chance To Impress His Crush

Angus (1995) - Poster

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Angus
Release Date
September 15, 1995
Runtime
90 Minutes
Director
Patrick Read Johnson
  • Cast Placeholder Image
    Charlie Talbert
    Angus Bethune
  • Cast Placeholder Image
    George C. Scott
    Grandpa Ivan
  • Headshot Of Kathy Bates In The CBS Fall Schedule Celebration At Paramount Studios
    Meg Bethune
  • Cast Placeholder Image
    Perry Anzilotti
    Tuxedo Salesman

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Angus is a 1995 coming-of-age film directed by Patrick Read Johnson. The story follows Angus Bethune, a socially awkward teenage boy, who navigates the challenges of high school life and bullying while discovering his self-worth and courage. The film features performances from Charlie Talbert as Angus and Chris Owen as his best friend, Troy, against the backdrop of a school dance that could change everything for Angus.

Bullies are a common theme in teen movies from 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 this movie to being a teen romance idol himself.

23 Bend It Like Beckham (2002)

Two Young Girls Go For Their Dreams Of Playing Soccer

Bend It Like Beckham

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Bend It Like Beckham
Release Date
April 12, 2002
Runtime
112 min
Director
Gurinder Chadha

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Jess is an Indian teenager who lives in England and dreams of following in the footsteps of her idol, British footballer David Beckham. But her family has more traditional plans for her.

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 play 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 while falling for their coach, played by Jonathan Rhys Meyers.

DID YOU KNOW: Despite their characters being the same age, Parminder Nagra is 10 years older than Keira Knightley.

Along with being a rare and excellent soccer movie, Bend It Like Beckham sets itself 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 feel-good sports movie about determined young girls that can inspire many others.

22 Edge Of Seventeen (1998)

A Young Boy Struggles With His Sexuality In The 1980s

Edge of Seventeen (1998) - Poster

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Edge of Seventeen
Release Date
June 14, 1998
Runtime
99 Minutes
Director
David Moreton
  • Cast Placeholder Image
    Chris Stafford
    Eric
  • Headshot Of Tina Holmes
    Tina Holmes
    Maggie
  • Cast Placeholder Image
    Andersen Gabrych
    Rod
  • Cast Placeholder Image
    Stephanie McVay
    Mom

WHERE TO WATCH

Streaming

Edge of Seventeen is a coming-of-age drama directed by David Moreton. Set in 1984, the film follows Eric Hunter, portrayed by Chris Stafford, as he navigates the complexities of adolescence, identity, and sexual orientation. With ing performances from Tina Holmes and Andersen Gabrych, Edge of Seventeen explores the challenges and triumphs of growing up and coming out in a small Midwestern town.

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 grips 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 itting 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.

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

21 Step Up (2006)

A Boy And Girl From Different Backgrounds Form A Bond As Dancing Partners

step up

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Step Up
Release Date
August 11, 2006
Runtime
98 minutes
Director
Anne Fletcher

WHERE TO WATCH

Streaming

Tyler gets the opportunity of a lifetime after vandalizing a performing arts school, earning him the chance to win a scholarship and dance with a promising dancer, Nora.

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 teens from two very different backgrounds who share 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.

DID YOU KNOW: Channing Tatum and Jenna Dewan were married in real life.

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.