10 Unforgettable Teen Romance Movies From The 90s & 2000s

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 rewatch. Moves from the 90s and 2000s had a certain charm that isn’t seen today on the big screen. This is especially true when regarding teen romance movies.

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Teen romance movies were a way to escape into a love story that seemed too good to be true. There was a popular boy and a quiet nerdy girl who somehow fall in love. In other cases, they were characters who were polar opposites who found their way into each other’s hearts. These types of movies have a way of sticking around for a long time.

10 Angus, Thongs And Perfect Snogging (2008)

Aaron Taylor-Johnson and Georgia Groome in Angus, Thongs And Perfect Snogging

For viewers who were still young teens during the 2000s, Angus, Thongs and Perfect Snogging was a hit movie. The movie had a bit of everything from embarrassing comedy, a quirky teen romance and the qualms of trying to get through adolescence. Based on a popular book series, the movie starred Aron Taylor-Johnson in the lead male role and Georgia Groome in the female role.

This movie helped put Taylor-Johnson on the map as a heartthrob before he hit it big in Hollywood. Georgia (Groome) gets a major crush on a new student 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 moments of being a teen.

9 Cruel Intentions (1999)

Ryan Phillippe and

Cruel Intentions became a cult classic from the late 90s when it came to a more twisted version of romance and drama. This movie isn’t the heart-stopping and blushing teen romance many would expect. Its storyline was based on a novel titled Les Liaisons dangereuses by Pierre Choderlos de Laclos in 1782.

The story is a bit dark, more mature in its theme but still became a favorite. It followed a privileged, upscale teen named Sebastian (Ryan Phillippe). He 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. Pulling out all his tricks, Sebastian never expected his cold heart to feel love.

8 The Prince & Me (2004)

Luke Mably and Julia Stile in The Prince & Me movie

The Prince & Me became a well-known romance movie from 2008 because it brought to life a storyline that only existed in fairytales. A normal country girl who gets a royal prince to fall in love. This isn’t necessarily a teen romance. Prince Edvard (Luke Mably) lives his life as a playboy and refuses to accept the responsibilities of his title.

He ventures to America to experience the fun college life. But he makes a bad impression with his lab partner, Paige (Julia Stiles). Despite trying to evade emotions, they fall in love. There’s one problem, she doesn’t know who he really is. A simple country girl might not fit into a posh and royal family.

7 Romeo + Juliet (1996)

Leonardo DiCaprio as Romeo and Claire Danes as Juliet

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 but with a modern twist. The movie became one of Leonardo DiCaprio’s recognized roles as a teen. The movie follows the same basic storyline of two teens who fall in love despite being part of rival families.

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In this version, the rival families are rival gangs. The movie adds more violence, drama and even drug use. When gate-crashing the famed Capulet party, Romeo takes ecstasy. The ending is kept relatively the same with the vials of poison and fated death, but instead of a dagger its a gun.

6 A Cinderella Story (2004)

Hilary Duff as Sam and Chad Michael Murray as Austin

Many who grew up in the 90s and 2000s have a fond memory 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 tagged as a teen heartthrob during the time thanks to One Tree Hill.

As the story goes, Sam (Duff) is a waitress in her father’s diner run by her cruel stepmother after his passing. There’re also mean stepsisters. 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 popular football player at school. Unable to reveal her identity, she flees at midnight leaving behind her cell phone. Now her Prince is on the hunt to uncover who she is.

5 Never Been Kissed (1999)

Drew Barrymore as Josie in Never Been Kissed

Never Been Kissed is that Drew Barrymore movie that many have a guilty pleasure for. The 1999 romantic comedy isn’t necessarily about teenage love, but 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. She didn’t expect to fall in love with her handsome English teacher. Her investigation comes to a halt when they want to use his story for the front page.

4 Twilight (2008)

Edward and Bella meadow scene in Twilight

Believe it or not, Twilight gets a spot on the list as being one of the most popular teen romances from the 2000s. The supernatural movie defined a time in the early 2000s where 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 like any other supernatural teen romance seen before. A seemingly ordinary girl named Bella (Kristen Stewart) has her life changed when she meets Edward Cullen (Robert Pattinson). She’s whisked into a dangerous love as Edward and his family are vampires. Not to mention her closest friend is part of a werewolf tribe.

3 She’s All That (1999)

Freddie Pricne Jr. as Zack and Rachael Leigh Cook Laney

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 bigshot on campus with friends, the popular girlfriend and golden opportunities. That’s until his girlfriend dumps him after meeting a celebrity during spring break.

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Now having his reputation and ego deflated, he makes a bet with his friend. He can turn any girl into prom queen material in six weeks. The target? Laney Boggs (Rachael Leigh Cook). The dorky, unpopular art girl.

2 A Walk To Remember (2002)

Mandy Moore as Jamie and Shane West as Landon

Based on Nicholas Spark’s book, A Walk To Remember became a coming-of-age teen one that had fans falling in love and bawling their eyes out. Landon Carter (Shane West) has no direction for his future and is rebellious. After falling into some trouble, he’s forced to take part in service duties.

One of them is taking part in the school play. Having difficulties, he seeks the help of the minister’s daughter who’s a nobody. She has one condition, he can’t fall in love with her. After treating her unfairly, he comes to realize that he broke his promise. There was a reason for her wish and they start a powerful romance that teaches them both life lessons.

1 10 Things I Hate About You (1999)

Julia Stiles as Kat and Heath Ledger as Patrick

The 1999 romantic comedy became a teen classic that was a box office hit and became the breakthrough roles for Julia Stiles, Heath Ledger, and Joseph Gordon-Levitt. 10 Things I Hate About You was also adapted from the Shakespeare play, The Taming of the Shrew but in a modern setting.

A new student named Cameron (Gordon-Levitt) becomes smitten with a girl. The problem is she’s not allowed to date until her ill-tempered older sister does so first. 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. They both end up falling in love. This movie has one of the most well-known love confessions in movies. 

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Updated: December 3, 2020 — 3:00 am

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