Though some may dismiss them as “chick flicks”, teen romance movies say a lot about each generation. John Hughes’ Pretty in Pink and Sixteen Candles showed the social dynamics of teenagers in the ‘80s, while Clueless and 10 Things I Hate About You reflected that snarky, angsty edge that most ‘90s teens seemed to embody.
But what do teen romance movies of the latest two decades tell us about the kids who grew up with these films? What kinds of stories did we get out of the teen romantic comedies of the aughts? Here, we list down eight of the best teen romance movies from 1999 onwards.
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8. To All The Boys I’ve Loved Before (2018)
Starring: Lana Condor, Noah Centineo, Israel Broussard, Janel Parrish, Anna Cathcart, Madeleine Arthur
What it’s about: Lara Jean Covey has two secrets: First, she’s in love with her sister’s ex-boyfriend, Josh. Second, she has written love letters to all five of her past crushes – Josh included. Her world is turned upside down when somebody finds and sends her letters, and she tries to dodge drama by convincing Peter Kavinsky – another recipient – to pretend to be her boyfriend. Slowly, though, the line between real and pretend blurs!
Why it made the list: While we haven’t had a decent rom-com in ages, this film’s release on Netflix seemed to mark the reemergence of the genre!
7. Love, Simon (2018)
Starring: Nick Robinson, Josh Duhamel, Jennifer Garner, Keiynan Lonsdale
What it’s about: When a mystery boy vents online about hiding his identity, closeted high schooler Simon Spier reaches out to him through email. The two slowly form a bond and Simon, burdened by his secret, finally feels like found someone he can be himself with. The only problem is, he has no idea who it is.
Why it made the list: While there are a lot of things to love about this film, it deserves extra praise for being one of the first gay teen rom-coms produced by a major Hollywood studio. Rarely do you ever see such a tender and sweet depiction of queer young love. Representation matters!
6. Nick And Norah’s Infinite Playlist (2008)
Starring: Michael Cera, Kat Dennings
What it’s about: If you liked To All The Boys I’ve Loved Before’s fake boyfriend/girlfriend gimmick, you’ll love Nick and Norah’s Infinite Playlist. Following a chain of events that begins with Norah begging Nick to be her five-minute-boyfriend, the pair take a wild and unpredictable road trip across New York City, dodging annoying exes and hunting down their missing drunk friend.
Why it made the list: Crazy characters aside, one of the best things about Nick and Norah’s Infinite Playlist is its soundtrack, featuring artists like Vampire Weekend, Devendra Banhart, and We Are Scientists.
5. High School Musical (2006)
Starring: Zac Efron, Vanessa Hudgens, Ashley Tisdale, Lucas Grabeel, Corbin Bleu, Monique Coleman
What it’s about: Troy and Gabriella are from opposite worlds. Troy’s a basketball star, Gabriella’s a science nerd. Neither have any interest in musical theatre, but when the two hit it off doing karaoke at a New Year’s party, they can’t seem to escape the pull of music – and each other.
Why it made the list: Though released as a TV movie under the Disney Channel Original Movie (DCOM) banner, High School Musical became so successful that the third and last film, High School Musical: Senior Year, became the first DCOM film to be released in theatres. Talk about bopping to the top!
4. Step Up (2006)
Starring: Channing Tatum, Jenna Dewan
What it’s about: Just like in High School Musical, Nora and Tyler are from different worlds – she’s a ballet student, he’s a rebellious hip-hop dancer. But when Tyler is sentenced to community service at Nora’s school, their worlds collide. And as Nora discovers Tyler’s talent, she changes his life in more ways than one.
Why it made the list: Step Up introduced the world to Channing Tatum. And for that, we will forever be grateful.
3. A Cinderella Story (2004)
Starring: Hilary Duff, Chad Michael Murray, Jennifer Coolidge, Regina King
What it’s about: In this modern-day twist on Cinderella, high schooler Sam is forced to live with and work for her evil stepmother at the family diner. As an outcast, she finds solace in confiding with her mystery penpal. But when the two finally meet up, their vast differences (and Sam’s evil stepfamily) complicates things for her.
Why it made the list: Jennifer Coolidge’s performance as Sam’s stepmother is so frustratingly good you’ll find yourself both annoyed and excited to see her on screen!
2. She’s The Man (2006)
Starring: Amanda Bynes, Channing Tatum
What it’s about: Loosely based on Shakespeare’s Twelfth Night, She’s The Man follows Viola Hastings, a soccer-playing tomboy who impersonates her brother, Sebastian, so she can join his school’s team. During her stay, she develops a crush on her roommate and team captain, the sweet but awkward Duke Orsino.
Viola finds herself in a hairy situation when she ends up helping Duke win over a girl even as she finds herself falling for him – all while he remains blissfully unaware that Sebastian is actually a girl!
Why it made the list: Amanda Bynes’ comedic chops really shine through in this film, and it’s hilarious seeing her try her best to cover up her girl-ness!
1. 10 Things I Hate About You (1999)
Starring: Julia Stiles, Heath Ledger, Joseph Gordon-Levitt
What it’s about: Kat and Bianca are sisters but couldn’t be any more different. Bianca is the life of the party, with boys chasing after her left and right. Meanwhile, Kat is anti-social and feared by most of the student body at their school. So when their overprotective father enforces a new rule stating that Bianca can only date if Kat does, the boys at their school devise a plan to get Kat to fall in love with the resident bad boy, Patrick.
Why it made the list: An oldie but a goldie, this love story introduced us to two of the best actors of our generation: Joseph Gorden-Levitt (still so young and cute here!) and Heath Ledger (RIP). We also got to see Heath bust out into song in a now-classic scene! Another classic moment? The scene where a tearful Julia Stiles recites all the things she hates (and loves!) about Heath’s character, Patrick.
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