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

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

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)

An Outsider Tries To Woo A Popular Girl At A High School Party

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

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.

26 The Girl Next Door (2004)

A Studious 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 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

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.

24 Angus (1995)

A Bullied Kid Gets A Chance To Impress His Crush

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

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

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

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.