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50 Years of Valentine’s Day Rom-Coms

Valentine's Day is known for reds, pinks, hearts and chocolate. These movies are reminiscent of the classic Valentine's Day aesthetic.
Valentine’s Day is known for reds, pinks, hearts and chocolate. These movies are reminiscent of the classic Valentine’s Day aesthetic.
Sloane Alexander

Valentine’s Day is a time to celebrate those you love – romantic, platonic, and everything in between. For those who don’t have romantic partners to spend the holiday with, there are countless rom-coms to get you in the spirit of the holiday, with or without a Valentine. I’ve chosen one from each decade starting in the 1980s to celebrate the holiday of love. From love letters to calls on landlines, exploring love throughout the decades is a perfect Valentine’s Day activity.

The 80’s–The Princess Bride (1987)

This classic has captivated audiences worldwide for decades. The story feels like a classic fairy tale, but with twists and turns that make it anything but antiquated. The film begins with a boy sick at home, as his grandfather cracks open a book to entertain him. The story that he shares is set in the mystical kingdom of Florin, where a girl named Buttercup is betrothed to the prince…but there are some complications. She is secretly still in love with her former love, Wesley, who died at sea years before. When Buttercup is taken by bandits, the story of love and betrayal begins.

The 90’s–10 Things I Hate About You (1999)

“10 Things I Hate About You” is a beloved rom-com. It’s hard not to love the enemies-to-lovers trope. The Shakespeare-based film, adapted from “The Taming of the Shrew, has captivated the hearts of teenagers worldwide. Following Kat Stratford, a strong, feminist teen, the plot is undeniably compelling. Kat seemingly despises all teen boys, but her strict father won’t let her sister, Bianca, date until Kat does. When a boy falls in love with Bianca, he schemes to set Kat up with a burnout teen who is just as closed off as she is. The plot explores love, stereotypes, and trust with countless iconic moments that will leave you swooning.

2000s–Princess and the Frog (2009)

This Disney movie is a heartfelt movie to bring back Disney nostalgia for any mood. Based on the fairy tale about a girl kissing a frog, the story details a romance between a prince and an aspiring restaurant owner. With music, love, and the comforting streets of New Orleans, the movie is sure to capture your heart. If you’re looking for a lighthearted option, this one’s for you.

2010s- To All the Boys I’ve Loved Before (2018)

“To All the Boys I’ve Loved Before” is the first of a movie trilogy that embodies the true purpose of Valentine’s Day, reaching out and expressing love when you feel it. The movie, based on the book series, follows a girl who mostly keeps to herself. When she starts developing romantic feelings for someone, she writes a letter and ends it there. This normally works to process her feelings without the risk of admitting her love face-to-face, until someone finds the letters and sends them. Then she has to deal with the messy aftermath of boys she used to (and might still) love. In the process, she decides to fake a relationship with one of the boys who received a letter, but it gets complicated when her feelings turn out to be more real than she expected. It is the closest this generation has come to the magic of a classic 90s rom-com.

2020’s- Bottoms (2023)

For some, Valentine’s Day brings up feelings of unrequited love and consequential anger. “Bottoms” is an exploration of female anger, partnered with the trials and tribulations of teenage love. The story follows two teens in the early 2000s, labeled “weirdos” due to their sexuality. They are entering their senior year, and pledged to finally win over the girls they have been in love with for years. They end up accidentally starting a fight club in the process, helping them take down the antagonist football player, whom everyone is obsessed with. The ridiculous interpretation of high school blends with the relatable portrayal of love and rejection to create a laughable comedy.

Any of these options will get you in the spirit of spreading love. Each leaves an iconic footprint on the history of film. Single or taken, they’re worth a watch.

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