Elisabeth Lee

Love, roses, chocolate, movies. Bundle up with these classic teen romantic comedies for Valentine’s Day.

With Valentine’s Day just around the corner, all’s fair in love and…movies? Just like how many holidays have specific movies geared towards the season, Valentine’s Day has a myriad of romantic-comedy movies that are certain to make you laugh, root for the couple, and show the journey of first love.

Sometimes the best movies are older ones, ones that provide comfort and nostalgia. Romantic-comedies in the ’90s and ’00s have some of the most iconic lines to quote, with relatable characters to see yourself in. 

So here are some must-see teen romantic comedies to watch if you ever feel like spending time with comfort characters and going on a romantic journey with them.

1) She’s All That

“So, can I have the last dance?” “No, you can have the first.”

She’s All That is a 1999 film that begins when a high school jock named Zack Stiler makes a bet with his friends that he can turn artistic nobody Laney Boggs into prom queen. But what he doesn’t realize is that halfway through the bet, he realizes that the more time he spends getting to know Laney, the more that he realizes that he doesn’t want it to be just a bet.

“I love the backstory with Laney, and how she’s a wonderful artist inspired by her mom,” Ashley Heather (11) said.

2) 10 Things I Hate About You

“I hate the way I don’t hate you. Not even close, not even a little bit, not even at all.”

This iconic 1999 film revolves around the Stratford sisters, Bianca, who is pretty and popular and Kat, who is anti-social and rebellious. A family rule forbids Bianca from dating until Kat gets a boyfriend of her own. A high school boy wanting to date Bianca attempts to set Kat up with Patrick Verona, another rebel who may just be able to win Kat’s heart. A perfect tale of love and hate, fighting and laughing, drama and peace.

“It’s funny, it has a good soundtrack, and the characters remind me of myself sometimes,” Violet Kowalski (11) said.

3) The Notebook

“So it’s not gonna be easy. It’s gonna be really hard. We’re gonna have to work at this every day, but I want to do that because I want you. I want all of you, forever, you and me, every day.”

The Notebook is a 2004 film about an elderly man reading to his wife who has dementia about two young lovers whose forbidden romance is threatened by their social classes. This Romeo and Juliet-esque story encompasses love and loss, showing how despite all the obstacles life throws at them, love prevails in the end, and nothing can keep them apart.

“I really like the authenticity of early 2000s movies,” Kayla Huizar (10) said. “I feel like the storyline is very raw, and the casting is incredible.”

4) My Big Fat Greek Wedding

“There are two kinds of people—Greeks, and everyone else who wish they was Greek.”

My Big Fat Greek Wedding is a 2002 movie that heavily emphasizes the theme of family, where a young Greek woman falls in love with someone who isn’t Greek, and has to try to convince her family to accept him. A story of acceptance, family, and cultural identity, My Big Fat Greek Wedding is a hilarious film that will have you on the floor laughing.

“It is absolutely hilarious and it’s kind of old-fashioned, which makes it even funnier,” Emily Schott (12) said. “The actors are so good and the plot is very enjoyable.”

5) How To Lose A Guy in 10 Days

“You can’t lose something you never had!”

How To Lose A Guy in 10 Days is a hilarious 2003 romantic comedy that involves a girl experimenting on trying to lose a guy in 10 days with a random guy. Unbeknownst to her, that same guy has made a bet that he could get her to fall in love in 10 days. These contrasting and comical gambles lead to hysterical one-liners, dramatic fighting, and swoony love. 

“It provides effortless laughter, but also scenes that make our heart swoon with love,” Malaia Reger (11) said. “It’s a definite re-watch for every season and has some of my favorite cinematic scenes.”

6) Legally Blonde

“You can do it The Washington Way, but I’m going to do it The Elle Woods Way.”

This 2001 film follows Elle Woods, a sorority girl who attempts to get her ex-boyfriend back by attending Harvard Law School. In the process, she overcomes the stereotype of being blonde as well as succeeding in finding her passion in law. Elle’s charismatic and headstrong personality make the film inspiring to watch.

“I like it because the message of the film is ‘you can do anything you put your mind to as long as you work hard.’ It’s absolutely amazing and inspiring to all ages,” Keira Vista (11) said.

7) Clueless

“Ugh, as if!”

Clueless is a classic and well-known 1995 romantic comedy that is about a beautiful and popular high school girl named Cher, who befriends a new girl and gives her a makeover. Upon this process, Cher realizes that there is more to life than clothes, makeup, and popularity. She realizes that maybe she is clueless about her own life and what she wants to accomplish.

“The elements of romance and comedy really pull this movie together and leave its audience with a great, and frankly, stereotypical representation of what being a high school student in the ’90s was like,” Melanie Medrina (9) said.

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Hopefully this guide helps you choose which classic romantic comedies you want to watch. Happy Valentine’s Day, and happy watching!