For many of us, when we think of fall staples, When Harry Met Sally is one that always comes to mind. It looks and feels like fall. It’s the kind of rom-com that most people think about when the genre is brought up because everything that the late and incomparable Nora Ephron and Rob Reiner achieve in the screenplay and directing, respectively, is masterful. It’s the kind of splendid combination that’s too rare nowadays. Genuinely perfect to the point where even if it’s not your favorite, you can’t deny its excellence.
It’s not my all-time favorite because that spot is reserved for While You Were Sleeping, but it’s the one that’s essentially synonymous with fall. It’s a quintessential friends-to-lovers romance that uses every moment to tell a thoughtful and gripping story that feels real.
Every Trope in When Harry Met Sally Feels Organic
There’s a misconception amongst people who think they’re too prestigious to consume a rom-com that it’s all mindless fluff and the easiest form of storytelling. Jokes on them, because there’s an enormous difference between writing tropes and executing them organically. In addition, romance as a genre isn’t just a cash grab, but it’s a nuanced, gorgeously evocative form of storytelling that highlights human experiences and fortifies connections in a uniquely groundbreaking way.
In other words, you can’t just decide you’re doing friends-to-lovers, opposites attract, and throw words onto the page. You have to not only ensure that the characters feel fleshed out, but also that their interactions fill every space possible to build the connection.
As a journalist, Ephron was no stranger to asking questions and trying to find the right answers. A large part of the reason why When Harry Met Sally is so beloved is because of the fundamental questions asked throughout that touch on our collective experience as humans. It’s a film from the late ’80s, yet still to this day, we ask ourselves: can two people truly be friends if they also feel the urge to sleep together? The web gets even more tangled when we explore the resources we have today. Social media gives us insight into people’s lives in a way that bumping into someone back in the day didn’t.
Still, the magic in Harry and Sally’s love story comes from the detail that despite living in a massive city like New York, they run into each other naturally. They orbit around each other for years, growing closer and closer while the threads between them form their own knots in the background. Interestingly, Ephron turned down Reiner and his producing partner Andy Scheinman’s original pitch for a movie about a lawyer. According to Ilana Kaplan’s Nora Ephron at the Movies, the screenplay for the movie originated from an organic conversation about dating. Presumably, Ephron even wrote in her picky eating habits as a quirk of Sally’s. The movie feels real because the events of the plot are tethered to real human experiences. They aren’t just fabricated.
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The story was built from understanding characters and their dynamics first, before anything else, which allows the tropes we now pay attention to to feel that much cozier—more lived in. As a result, we have a movie that we can keep watching over and over again and still discover something new every time. That’s what happens when your characters take a front seat to the plot: magic glitters in every frame.
The Heart Is Unbeatable
There are few things nowadays that feel cozier than a ’90s rom-com that’s full of laughs, gorgeous scenery, yearning, and a more simple approach to everything. That simplicity is so easy to miss now when everything around us is powered by AI, and we’ve lost so much authenticity and genuine human connections. From the screenplay to every directorial decision, When Harry Met Sally is raw. It’s real. Meg Ryan and Billy Crystal redefine what a brilliant performance should look like, and everything about it feels memorable because of the execution.
This is the part of talking about ’90s rom-coms that I can rarely find the right words for, but I suppose it all comes down to the simplicity. I miss catching up with people and hearing about their endeavors in person rather than through social media. “Get off social media,” someone will say, but I can’t exactly do that when so much of my job centers around it. It’s the fact that the climate’s changed so drastically that fall comes later now. Heat waves delay the joy of a biting early morning in September. Movies are now bogged down by excessive CGI, odd color-grading techniques, and are mere cash grabs as opposed to character studies.
When Harry Met Sally is only an hour and 36 minutes long, yet we can write dissertations on who both characters are because everyone involved in the movie knows them. The simplicity in ordinary interactions easily becomes far more intimate, and the more you watch it, the more revelations open up. The wardrobe is stunning. The music feels triumphant. The performances are layered. The directing is stunning. The screenplay is so sharp and so breathtaking that words will never do it justice.
It feels like catching up with old friends every time you turn it on. It’s not so much about nostalgia as it is about the heart of it all. The essence, the warmth, and every little detail in between that, in short, sparkles like an afterglow you have to stop and marvel at every time the sky decides to show off.