What Decades of Rom-Coms Taught Me this February

We’re constantly flooded with new streaming drops and whatever is trending on social media, but there’s a real comfort in going back to the classics. This Valentine’s Day, I found myself revisiting four films that define the spectrum of human connection: 10 Things I Hate About You, Love Actually, La La Land, and When Harry Met Sally. Watching them back-to-back was very emotionally impactful, showing how beautiful love can be. 

I started the evening with the sharp, rebellious energy of 10 Things I Hate About You. There is a reason this late-90s gem remains the gold standard for teen rom-coms. The characters were very well written, and everything in the movie is so pleasing to see. It perfectly captures that terrifying, exhilarating moment of realization that you’ve fallen for the one person you swore you wouldn’t. It’s loud, it’s messy, and it’s undeniably fun, the ultimate starter for a romantic night in. Fun fact: the movie is a loose adaptation of the Shakespearean comedy The Taming of the Shrew! 

Moving from the angst of high school to the sweeping, bittersweet streets of modern Los Angeles, La La Land remains a visual and emotional masterpiece. Every time I watch it, I am struck by how it balances the whimsy of a classic musical with the grounded reality of ambition. It’s a film that understands that sometimes, loving someone means letting them go so they can become who they are meant to be. The ending never fails to leave me breathless, caught between the joy of what was and the “what if” of what could have been.

Of course, no Valentine’s celebration is complete without the cozy, interconnected chaos of Love Actually. While some call it sentimental or a Christmas film, I find its sprawling narrative to be a beautiful tribute to the idea that love is, quite literally, everywhere. From the grand gestures at an airport gate to the quiet, heartbreaking moments of a marriage in transition, it feels like a warm hug in cinematic form. It’s the kind of movie that makes you want to pick up the phone and call everyone you care about.

I ended my journey with what I consider to be the perfect screenplay: When Harry Met Sally. Decades later, the chemistry between Billy Crystal and Meg Ryan remains unmatched. It asks the age-old question of whether men and women can ever truly be “just friends,” but more importantly, it explores the beauty of a love built on a foundation of genuine friendship. The New Year’s Eve monologue is, in my opinion, the greatest profession of love ever put to film.

Together, these four movies offer a complete map of the heart. They reminded me that love isn’t just one thing; it’s a friendship, a sacrifice, a grand gesture, and sometimes, a poem written on a piece of notebook paper. This year, skipping the new releases for these proven classics was the best Valentine’s gift I could have given myself.

If I had to rank them based on this year’s viewing, When Harry Met Sally remains the undisputed champion for its intellectual depth, while La La Land takes the prize for the most emotional impact. 10 Things I Hate About You is a shot of adrenaline for anyone feeling a bit too cynical about the holiday, and Love Actually serves as the perfect, messy reminder that none of us are alone in our pursuit of connection. 

Whether you’re watching these films with a partner of twenty years or a bowl of popcorn and your own company, these four films prove that the best way to celebrate Valentine’s Day isn’t with a gift you can wrap, but with a story that makes you feel a little more human.