There’s finally a chill in the air. The kind of crispness that makes you crave sweaters, lattes, and a good romantic comedy. For me, fall officially begins the moment I hear that familiar piano score from When Harry Met Sally. It’s the ultimate cozy-weather movie: full of New York park benches, changing leaves, and warm conversations.
But here’s the thing: I don’t just watch When Harry Met Sally for comfort. I also love defending it from the people who think it’s overrated, outdated, or even problematic. Yes, I’m talking about the unpopular opinions that float around the internet (and sometimes across your couch).
I once knew someone who hated Billy Crystal’s character, Harry Burns. Thought he was a smug jerk who only wanted to sleep with Meg Ryan’s Sally. He’d roll his eyes at every quip and mutter how he was so much better than him. That was one of the first clues that he was far from what I was looking for. Because if you can’t handle Harry at his neurotic, self-deprecating best, you don’t deserve him at his “I came here tonight because when you realize you want to spend the rest of your life with somebody…” speech.
“Harry Burns is a jerk. Why would anyone fall for him?”
This might be the most common unpopular opinion. Some viewers argue that Harry is selfish, emotionally unavailable, and deeply cynical. Not exactly rom-com hero material. Some reviews I’ve read online have bluntly called him “rude and condescending,” while others describe him as “smug” or “manipulative.”
And to be perfectly honest, I get it. In the beginning, Harry is kind of the worst. He’s that guy who thinks every conversation is a debate club meeting. He tells Sally that men and women can’t be friends because sex always gets in the way, and he does it while chomping on grapes and spitting them out in her car.
But that’s also the point. Harry’s whole journey is about learning to soften. Nora Ephron, the screenwriter (and rom-com genius), based much of his dialogue on real conversations she had with her friends and director Rob Reiner. So yeah, Harry feels a little too real. He’s the kind of guy you roll your eyes at until, suddenly, you realize you’re quoting him at dinner parties.
By the end, Harry’s vulnerability wins you over. When he blurts out that he loves Sally because she gets cold when it’s 71 degrees, that’s not a line from a “jerk.” That’s a man who finally understands intimacy.
“The idea that men and women can’t just be friends is outdated.”
Another common critique: the movie’s central question of Can men and women ever just be friends? It feels a bit like something out of an 80s office comedy. Some modern viewers say it reinforces heteronormative assumptions or oversimplifies male-female friendships.
Fair point. If this movie were made today, the question might look different (or at least include a broader range of relationships). But I think the brilliance of When Harry Met Sally is that it doesn’t give an easy answer. It asks the question, but it doesn’t insist on a universal truth.
The film uses that premise to explore emotional closeness: how friendship can slowly transform into something deeper. It’s not that men and women can’t be friends. It’s that Harry and Sally couldn’t pretend that’s all they were.
A University of Melbourne review put it best:
“The film answers the question that Harry and Sally were never friends and never meant to be friends — but its analysis of love, friendship, and adulthood is far more interesting than the great gender divide.”
On The Everlasting Charm of “When Harry Met Sally,” 2023.
To me, that’s what makes it timeless. Even if the conversation starts in 1989, the emotions are still relevant. We’ve all had that friend who lingers in the “what are we?” gray zone, and When Harry Met Sally just puts words to the tension.
“It’s too New York, too privileged, too ‘perfect’ to be relatable.”
Some critics argue the film romanticizes a very specific kind of urban life: successful, witty New Yorkers who spend their days brunching, bookstore browsing, and walking through Central Park. One New York Times review even called it “an often funny but amazingly hollow film.”
But I think that’s part of its appeal. The crisp brownstones, the bookstore montages, the Central Park walks! It’s aspirational but grounded. It captures the mood of a season. Fall in When Harry Met Sally isn’t just weather, it’s a metaphor for change.
Watching it feels like stepping into an ideal version of adulthood. One where your biggest problems are emotional rather than existential. And isn’t that kind of escapism exactly what we want when the temperatures drop?
The case for it being the perfect fall movie
Let’s be honest: When Harry Met Sally basically invented the “fall aesthetic” before Pinterest even existed. Between the cozy sweaters, the golden leaves, and that timeless “I’ll have what she’s having” diner moment, it’s a masterclass in seasonal comfort.
Here’s why it works so well when the temperature drops:
- The Visuals: Warm tones, layered clothes, and that golden-hour New York light.
- The Soundtrack: The jazzy renditions of “It Had to Be You” and “Don’t Get Around Much Anymore” are autumn.
- The Mood: The film isn’t about dramatic twists; it’s about time passing (just like the seasons). Harry and Sally grow up, fall apart, and circle back, mirroring the rhythm of nature itself!
- The Theme: Fall is about transition. About realizing what to hold onto and what to let go. That’s the movie in a nutshell.
A man, the movie, and the red flag I didn’t see coming
Back to the dreaded man (because what’s a rom-com article without one?).
We were on the couch with the opening credits rolling. I was beaming, ready to share my all-time favorite film. About fifteen minutes in, he’s already dismissing it. “This guy’s a jerk. He’s literally trying to manipulate her.”
He wasn’t wrong that Harry had flaws. But the way he said it, the total lack of empathy, the dismissal of Harry’s evolution, told me everything I needed to know. He saw the surface, not the growth. He wanted black-and-white answers, not slow character development.
Somewhere between Harry’s “men and women can’t be friends” and the diner scene, I realized: I didn’t want to date someone who couldn’t understand emotional nuance. Someone who missed the humor, the longing, the soft contradictions.
Because loving When Harry Met Sally means loving imperfection. It means believing people can change. It means rooting for connection even when it’s messy. And if someone can’t see that, well, that’s their loss.
Falling for Harry (and the season) all over again
Every year when the air turns cold, I put the movie on again. I laugh at the same lines, I smile at the same confession, I get a little misty when Harry runs through New York on New Year’s Eve.
Maybe it’s because the movie reminds me that love doesn’t always announce itself with grand gestures. Sometimes it’s two people walking through the park, talking about Casablanca, realizing (slowly) that they’ve become each other’s person.
When Harry Met Sally is funny, flawed, smart, and tender, just like the fall season itself. It reminds me that relationships (and people) evolve. That cynics can become romantics. That fall is a good time to let go of wrong expectations and even the wrong people.
So this year, as the leaves turn and the pumpkin spice lattes appear, I’ll be watching When Harry Met Sally for the hundredth time. Because no matter what the internet says, or what a man might argue, Harry Burns will always have my heart.
“When you realize you want to spend the rest of your life with somebody, you want the rest of your life to start as soon as possible.”
When Harry Met Sally (1989)