Top 20 Cute Movies: Teenage Romance

Choosing just a few of the teenage romance movies out there is a challenging task. There are so many available over the last few decades that narrowing down the list has been beyond difficult. If we missed one of your favorite teenage romance movies (and I am sure that we will—after all, 20 does not even cover all of my personal favorites), then leave a comment at the bottom of the article with your top choices.

20. Never Been Kissed

Starring the phenomenal Drew Barrymore and David Arquette, this movie also contains Molly Shannon and Michael Vartan. For those of you who grew up after the 1990s, David Arquette’s claim to fame (at least in my mind!) is that he was married to the lovely Courtney Cox of Friend’s fame. Basically, the story line from this 1999 film follows the tale of a journalist who is forced to enroll in high school for a story. After not having a terribly awesome time in high school the first time through, she is in for a very surprising experience this time. Romance, typical teen high school stories and a good performance by Drew Barrymore make this movie worth watching.

19. Romeo and Juliet

Whether you are a fan of Shakespeare or not, you need to see this movie. If you are a fan of Shakespeare, keep a very open mind because this is a completely remodeled, updated take on the classic story line. With Claire Danes and Leonardo DiCaprio, you have a sentimental love story set in modern day Florida (or at least, what looks like Florida). Instead of swords, this Baz Luhrman take on Shakespeare has machine guns and fast cars. It is essentially a wild party from start to finish as two gangster/mafia families go at each other’s throats. Produced in 1996, this is an excellent film to fill your afternoon or date night.

18. A Walk to Remember

The scene: North Carolina. The characters? Two juvenile teenagers from opposite sides of the popularity spectrum end up falling for each other. Directed by Adam Shankman, this movie stars Shane West, Mandy Moore, Daryl Hannah and Peter Coyote. After hitting theaters in 2002, it quickly became one of the most popular teenage love stories of all time. It follows the tale of Landon Carter and Jamie Sullivan. While Landon is a fairly typical teenager, Jamie is an unstylish girl with leukemia. Like most stories of its class, the two end up falling for each other. Landon quickly starts to help Jamie finish off her bucket list (before bucket lists were a thing, of course). The ending will remain in your mind for days afterward.

17. 10 Things I Hate About You

In this classic coming of age film, the main characters are Bianca, Cameron and Kat. The story starts with Cameron joining a new school. Before long, he falls for the immensely popular and unbelievably gorgeous Bianca. He wants to date the beautiful Bianca, but her father stands in the way. While neither girl was allowed to date, their father decides that Bianca can have a boyfriend if Kat is dating as well. With the lovely Bianca in mind, Cameron sets out to find out exactly what Kat wants in a guy so that he can find her a boyfriend and win the hand of the beautiful Bianca.

16. Almost Famous

Released in 2000, Almost famous stars Billy Crudup, Kate Hudson, Patrick Fugit and Frances McDormand. Directed by Cameron Crowe, it tells the story of a goal-oriented, super intelligent high school boy who wants to be a journalist. After being home schooled for his entire life, William is not accustomed to the ways of rock and roll. With the help of a mentor, he ends up getting the opportunity to write for Rolling Stone Magazine. He starts to follow the band on their concert tour and mingles with the groupies he meets along the way. William falls for the gorgeous Penny Lane, but a positive outcome for his crush seems impossible. This movie will keep you riveted to your seat until the very last moment.

15. Chasing Liberty

Try out a different take on the classic guy meets girl and falls in love. With this tale, the girl involved is the daughter of the president of the United States. Anna is stifled and overwhelmed by the Secret Service protection that she is assigned. After a great deal of protesting the situation, her father lowers her guard to just two people. Anna ends up going to a concert and sees multiple Secret Service agents, so she ends up getting upset and assuming that her father lied. Following this experience, she is overseen by an undercover Secret Service agent named Ben. She is not aware that he is a Secret Service Agent, and they quickly begin to fall in love. Only after he has left the Secret Service do they have a chance to really live out their relationship.

14. The Notebook

There are few tales as classic as the Notebook. Although it does not strictly focus on teenagers it is still a story that will have you in tears. In this 2004 film, Noah is just a poor mill worker who falls in love with Allie. Unfortunately, Allie is an heiress whose parents have the ability to keep her apart from Noah. Years later, she meets up with him and falls in love again. The film bounces back and forth between their love story and the present, where Allie is incapacitated by Alzheimer’s. Unable to remember their story, Allie is reminded of their love through a notebook that tracked the entire love story.

13. Juno

Released in 2007, Juno stars a 16-year-old girl. Experimenting with sex for the first time with a friend, she ends up becoming pregnant. Originally, she considered the possibility of just having an abortion. After thinking things through, she decides that she wants to give the child up for adoption. She finds the perfect family, but the perfect family is far less than perfect. The husband in the adoptive couple, Mark, ends up falling for Juno. This causes his marriage to fall apart, so the “perfect” adoptive couple is no longer able to adopt. Beyond the stress of the pregnancy and losing the perfect adoptive family, Juno is also left to figure out her feelings for the father of her child, Paulie. Are they friends or is there more? Watch the movie to find out.

12. Sixteen Candles

You may know Molly Ringwald as the mother in the Secret Life of the American Teenager. Before she was a mothering figure, she was one of the most popular teenage stars of her day. Released in 1984, Sixteen Candles stars Molly Ringwald, Justin Henry, Anthony Michael Hall and Michael Schoeffling. In the movie, Molly Ringwald has just turned 16 years old. Unfortunately, her sixteenth birthday is anything but sweet and she has to deal with one of the worst embarrassments possible. The main character, Samantha (Molly Ringwald), has a crush on a cute boy called Jake, but she is afraid that her decision to be chaste will turn him off. Meanwhile, she has to fend off the attention of nerdy Ted who has developed a crush on her.

11. 17 Again

Released in 2009, 17 Again was a part of the trend surrounding teenage pregnancy. With multiple teenage pregnancy shows on the airwaves, it only made sense that the movie industry would copy the trend. Mike finds out in this movie that he is going to be a father. Instead of going to college like he expected to, he runs after his girlfriend, Scarlett. A decade passes and the couple ends up separating, although they now have two children again. Mike returns to his old school, and a magical janitor returns him to the age of 17. He goes to the modern-day school as a 17 year old version of himself with a friend’s son. While at the school, he meets his children and learns about what they want from a different perspective. Meanwhile, he also meets Scarlett again and learns the real reason why they broke up. Realizing his selfishness caused everything, he tells Scarlett the truth and is returned to his previous form.

10. When in Rome

Released in 2010, When in Rome stars Kristen Bell, Danny DeVito, Josh Duhamel and Angelica Huston. It follows the tale of a New Yorker named Beth. Goal driven and ambitious, Beth has never had a successful love life. Instead of trying to work things out, she plans out a whirlwind trip through historic, romantic Rome. While at the fountain of love, she steals a few of the coins. What happens next leaves her in shock: an entire group of suitors starts to pursue her. Directed by Mark Steven Johnson, this is a cute romance with a twist.

9. The Last Song

At the age of just 17 years old, Ronnie is something of a piano prodigy. When her parents decide to get divorced, she becomes rebellious and stops playing piano completely. After not seeing her father for a number of years, she moves to spend the summer with him, and her brother goes along. While there, she ends up getting to know her father better and starts to fall in love with a bot she meets named Will. This tale is part journey of self-discovery and part love story. Overall, it is entirely worth the few hours it takes to watch it.

8. Flipped

Released in 2010, Flipped follows the story of Juli and Bryce. These two first met when they were in just second grade. At the time, Juli is convinced that she has found true love. Bryce is not so certain—he spends most of the first six years of their relationship trying to avoid her as much as possible. Bryce’s grandfather changes this entire situation. His grandfather, Chet, moves in with Bryce’s family and grows attached to the young Juli. With the grandfather playing matchmaker, Bryce soon begins to learn that Juli is the incredible, rare person that he has been looking for.

7. Beastly

Released in 2011, this is a modern remix of the classic fairy tale, “Beauty and the Beast”. In the tale, a New York City teenager is transformed into a hideous beast so that they can find someone who loves them for who they really are. A bit of a cheesy story line, but it offers a fresh take on the classic tale and has the strange ability of drawing you into the story despite your realization that it is a bit on the cheesy side. Directed by Daniel Barnz, this story stars Mary-Kate Olsen, Alex Pettyfer, Justin Bradley and Vanessa Hudgens.

6. Moonrise Kingdom

Released in 2012, this film is actually set in the 1960s. It stars Sam and Suzy, two affable teenage runaways. Only 12 years old, they have decided to escape from normalcy and enter into a new adventure. While Suzy is an intelligent, precocious girl, Sam is more grave and nerdy. With many amusing, humorous moments, the story follows them to their first kiss on a beach as they experience the world first hand.

5. A Cinderella Story

Released in 2004, this is another movie that puts a modern spin on a classic fairy tale. Unsurprisingly, the story tells of the lovely Sam Montgomery who is kept down and exploited by her evil step-mother. Despite her problems, she is excited about meeting her Internet boyfriend at her high school’s upcoming Halloween dance. Directed by Mark Rosman, this tale stars Hilary Dugg, Dany Byrd, Chad Michael Murray and Jennifer Coolidge. For a cute way to pass the time, A Cinderella Story is worth the 95 minutes that it takes to watch it.

4. Clueless

Clueless is a a modern remake of Jane Austen’s Emma (surprise!). It follows the tale of the super rich, popular and exceptionally shallow Cher. She is at the top of the Beverly Hills High School food pyramid and is involved in everyone’s social life. Played by Alicia Silverstone, Cher is a matchmaker who convinces two of her teachers to date each other. After this initial encouragement, she decided to turn to hooking up other people. Enter Tai (Brittany Murphy). Tai is a klutzy, awkward student who is hopelessly in need of a makeover. Tai eventually goes for Cher’s former step-brother, Josh (played by Paul Rudd), and Cher realizes too late that she likes her former step-brother as well. Released in 1995 and directed by Amy Heckerling, this is a classic teenage romance with all of the matchmaking of the original Emma.

3. Titanic

Titanic is one of the most popular romances of all time. Epic—literally, it is hours long—and unfortunately tragic, it stars Kate Winslet and Leonardo DiCaprio. In the film, these two teenage/young adults are both setting out for an adventure in America. The lovely Rose (Kate Winslet) is a society girl who is from an old aristocratic family. Unfortunately, her family has lost most of their wealth, so she and her mother are hopping the infamous Titanic for a new life in America. She is engaged to a wealthy aristocrat at the beginning of the movie, but he is a bit of a jerk. Meanwhile, Leonardo DiCaprio plays the charming Jack. Growing up in poverty, Jack has lucked into a steerage ticket on the Titanic. Before long, he meets with Rose and begins to fall in love with her. Their story is one of the most romantic, moving love stories of all time. If you have never watched the Titanic in your life, you need to clear your weekend schedule and hunker down with a box of Kleenex.

2. Mean Girls

Before Lindsay Lohan became a tabloid favorite, Mean Girls was one of her most popular films. It is satire at its finest in the way it makes fun of the normal high school groups and popularity contests. Cady Heron (Lindsay Lohan) grew up in Africa with her parents. After being home schooled for her entire life, the intelligent but socially awkward Cady enters an American high school. She gets a first hand experience in the cruel world of popularity contests and cliques. Her particular school is ruled by a group of Barbie doll wanna-bes called the Plastics. Before long, Cady makes a plan with her fellow geeks to take on the Plastics and transform the school. The only question is if she will lose herself and the guy she loves in the process.

1. Dirty Dancing

Dirty Dancing was released in 1987 and starred Jennifer Grey and Patrick Swayze. During the summer, Frances “Baby” Houseman (Jennifer Grey) goes on vacation with her family to the Catskills. The youngest in her family, she has a goal of studying at Mount Holyoke College before joining the Peace Corps. While on vacation, she begins to take dance lessons from Johnny Castle (Patrick Swayze). What begins as just dance lessons quickly becomes a massive crush for Baby. Before long, she discovers the secret world of “dirty dancing” practiced by the staff members and wants to join in. As she starts to dance with him and spend more time with Johnny, she falls in love with the guy from the wrong side of the tracks.