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Wednesday, Dec. 17, 2025

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AYSW? | Rom Com Classics of the Nineties and Oughts

Reading time: about 4 minutes

In the ’90s and early 2000s, romantic comedies were truly at their peak — they just don’t make them like that anymore. Perhaps it’s the grand gestures, the witty banter or the joy of watching people come together in the simplest and purest form. There’s something undeniably comforting about the hopeful optimism these films capture — an idealized version of life that feels a little lighter and warmer. Whether you’re in the mood for a laugh, a good cry or just something warm and familiar, here are a few of my favorite rom-coms that are always worth a rewatch. 

Clueless

I think every young girl has dreamed of being a little like Cher — well-dressed, confident and effortlessly put together. But what makes Clueless such a beautiful movie is that, beneath Cher’s image as the rich, fashionable Beverly Hills girl, she is actually incredibly smart and resourceful. She cleverly sets up her teachers to boost her grades, navigates the chaos of high school with her witty strategies and genuinely tries to help others — like when she mentors a new student through the social scene of high school. Yet, she’s “clueless” in her own way, as she finds herself caught up in material things and popularity. Still, what I think people often overlook is her heart: her kindness, her loyalty and her willingness to grow. It’s the ultimate rom-com in disguise — beneath all the humor, outfits and teenage drama, the movie is really about self-discovery and realizing that sometimes the person you’re looking for has been right in front of you all along. Personally, I love this movie — it never fails to put me in a good mood. 

Seredepidity

I learned what the word serendipity meant through this movie — “a happy accident” or unexpected good luck. It is a whimsical and perfectly cozy Christmas film. Starring John Cusack and Kate Beckinsale, it follows two strangers whose chance encounter sparks years of missed connections and near encounters. I remember watching it for the first time and feeling so frustrated and annoyed — the entire chain of missed events could have been avoided if she had just given her phone number instead of writing it in a book, and if he hadn’t scribbled his on a dollar bill. But that’s the funny thing about fate, when something is meant to be, it always finds its way back. It’s the kind of story that makes you believe that time, no matter how chaotic, always has its own plan.

10 Things I Hate About You

The classic bad boy and feminist girl love story. I think I knew this movie was going to be a personal favorite the moment Patrick started serenading Kat on the bleachers with his rendition of “Can’t Take My Eyes Off You.” Or when Cameron tells Bianca, “I learned French for you.” And then, of course, there’s the final poem — the one where Kat lists all the things she “hates” about Patrick. Based on Shakespeare’s The Taming of the Shrew, the movie gives the play a modern high school twist: Kat’s strict dad won’t let her younger sister date until she does, leading to a scheme to set Kat up with the mysterious Patrick — and, of course, they unexpectedly fall for each other. It’s corny and genuinely funny, capturing the chaos of high school — the mix of independence, vulnerability and the pressure to fit in. What I love most is its message about staying true to yourself and not letting others define who you are — something that still feels incredibly relevant in the world we live in today.

Notting Hill

Julia Roberts and Hugh Grant. Need I say more? These two are the quintessential rom-com duo. Notting Hill is the story of a famous actress who unexpectedly falls in love with a humble London bookseller, and somehow it feels entirely believable. I’ll admit, the movie starts off slow, but that’s part of its charm: the awkward pauses, quiet glances make their connection feel soft, pure and real. It isn’t loud or overly dramatic; it unfolds naturally, full of moments that make you smile. To me, it’s a film about finding something genuine in a world that often feels anything but. It urges us to take risks even when the odds seem impossible. 

‘Are You Still Watching?’ is a column spotlighting what the Cornell community has been streaming. It runs every Wednesday.

Alex Chou is a junior in the College of Architecture, Art, and Planning. She can be reached at apc97@cornell.edu.


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