When Harry Met Sally turns 36 — July 12, 2025
So the thing about When Harry Met Sally, which you probably know as "the movie with the orgasm scene" and possibly as "the ur-text of the modern romantic comedy" and which Nora Ephron herself came to be slightly annoyed about being primarily known for — it's a 1989 movie about people who graduated from the University of Chicago in 1977, which means it's a movie about a very specific cohort that a lot of people have forgotten existed, which is: people who were born around 1955, missed the actual sixties entirely (you were 13 in 1968, which is the wrong age to have done anything), graduated into the Carter economy, and spent their twenties in the disco-into-Reagan transition that nobody has a good name for because nobody wants to claim it — and the movie is completely about this, it's about what happens when you're old enough that the sexual revolution is just ambient background radiation you grew up in rather than something you fought for, so you get all the license and none of the politics, which means you get to be cynical about sex in a way that would have been unthinkable to someone ten years older and embarrassing to someone ten years younger.
Harry is a political consultant. Sally is a journalist. They are bourgeois in a very particular late-70s/early-80s upwardly-mobile way — the movie is set in New York and the New York is the New York of Ed Koch, not the New York of the 1970s fiscal crisis, it's the city on the way up, and their apartments look like it, their careers look like it, their whole problem is a rich-people problem which the movie never once acknowledges as such because in 1989 this was just what movie people looked like.
The Katz's scene is the thing everyone remembers and it's so heavily mythologized (the "I'll have what she's having" line is carved into the booth) that it obscures what the scene is actually doing, which is a pretty aggressive argument about heterosexual miscommunication delivered in a register — woman publicly simulating orgasm in a deli to prove a point to a man about whether he would know — that in 2025 would read as either radical-feminist didacticism or cringe, but in 1989 was mainstream romantic comedy, this was the Thanksgiving movie, this played in Peoria. The frankness is the artifact. Nobody would make that scene now. Not because it's offensive but because it's too arguing, it's too interested in making a structural point about sex to be allowed inside the genre anymore — the rom-com as it evolved through the 90s and early 2000s (which WHMS basically invented as a genre) systematically removed the sociological content and kept only the meet-cute-to-wedding scaffolding, which is why the Katz's scene feels weirdly unlike the movie it's from if you only know it from clips.
The other thing is that Ephron was writing Rob Reiner's love life — Reiner had just gotten divorced, was depressed, kept telling Ephron horrible things about being a single man in his late thirties in Manhattan — and Ephron took his material and a bunch of her own material and made it into a movie that's structurally a Woody Allen movie (split-screen phone calls, walking-and-talking in autumn Central Park, the Gershwin, Jesus Christ the Gershwin) but with the Allen persona surgically removed and replaced with what is essentially Rob Reiner's therapy, performed by Billy Crystal doing Rob Reiner. Think about that for a second. The film that launched modern romantic comedy is a Woody Allen cover version performed by a director who was working through his divorce via his female friend's screenplay. The whole thing is a hall of mirrors and the mirror at the center is Reiner's loneliness, filtered through Ephron's ear for how men and women actually talk to each other, filtered through Billy Crystal's delivery, which softens Reiner's native abrasiveness into something female audiences could tolerate as a romantic lead.
What the movie argues — and this is where it's dated in the most interesting way — is that men and women can't be friends because sex always gets in the way, and it argues this as if it's a controversial claim that requires 95 minutes of screen time to establish, which tells you how much ambient optimism about post-revolution gender relations was still in the water in 1989. The premise of the argument is that the sexual revolution was supposed to have solved the friendship question — if sex isn't a big deal anymore, why can't men and women just hang out? — and Harry's position is that it didn't solve it, it just made the unsolvability less discussable, and the movie ends by agreeing with him, which is a fairly dark conclusion dressed up in a New Year's Eve kiss. The structural pessimism about heterosexuality is the actual engine of what reads as a feel-good movie, which is probably why it aged better than its imitators — the 90s and 2000s rom-coms inherited the scaffolding and threw out the pessimism, and without the pessimism the form is just machinery.
Another thing: the movie is obsessed with telling the story of how a couple met — the old-couple interviews interspersed throughout are a genius structural device that accomplishes about four things at once (tonal punctuation, thematic underlining, sociological documentary texture, and a running argument that every couple's story sounds stupid when you tell it, which is the movie's actual thesis about itself) — and this device was specifically mining the Studs Terkel-era appetite for oral history, which was a 1970s cultural product that was mostly dead by 1989 but whose aesthetic Ephron grabbed on the way out. Nobody would shoot those interviews now. They'd feel too slow. They'd also feel too real — they have the texture of actual documentary because Reiner shot them with actual couples first and then had actors redo the best ones, which is why they feel weirdly authentic compared to everything around them.
The movie is thirty-six years old. The characters, if they existed, would now be seventy. Their children, if they had any, are older than the movie's main characters are. The sexual revolution they were in the tail-end of is now something that happened in the deep past. And the genre it founded has largely collapsed under the weight of its own conventions, which is maybe just what happens when you strip-mine a specific sociological moment for a genre template and then run the template for thirty years past the moment.
Or maybe the genre collapsed because streaming killed the mid-budget adult comedy and this has nothing to do with the content of the movies at all, which would be a boring explanation but probably the correct one.
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