
Steve
Rob Reiner’s 1989 Romantic Comedy When Harry Met Sally is easily one of the most memorable movies of that decade. Whether it’s the influence it’s had on the genre since, or the feel-good performances of it’s stars, or just the right mix of romance, meaningful moments, comedy, and Meg Ryan moaning.
In any case, it’s a movie that (while remembered fondly) has eluded being talked about on this channel for years. And today, I am facing that broken thread once and for all because folks, what you don’t know is that THIS movie is the birth place of almost every romance trope in movies today. Like, before this movie-there was no “high-maintenance girlfriend” trope, no “Transitional Lover” characters filling the screen, no frenemies to lovers scenarios that have since ruled the plots of nearly every rom-com to release in this movie’s wake. It is…kind of a big deal.
What’s When Harry Met Sally about?
When Harry Met Sally follows the story of the titular Harry Burns and Sally Albright. The film spans from their senior year in college to the present day and tracks how they went from two strangers forced to endure eachother’s company on a road trip-to becoming a sweet old couple that finishes each other’s sentences. But what the story is all rooted in is a question Rob Reiner had on his mind during his time as an adult bachelor: Can men and women TRULY be “just friends?”
See, this movie ain’t “The Notebook”, it’s not a blossoming relationship that meets circumstantial turmoil that tests their love. It’s more like seeing two people learn each other over the course of years in an unromantic way, that eventually see their relationship for what it has always been.

The role of Harry Burns is played wonderfully by Billy Crystal, and Sally of course is played by Meg Ryan who (at that time) was one of the most beloved “girl next door” types in Hollywood. Crystal and his sweaters are iconic to the movie now, but before he was even considered for the part-names like Tom Hanks, Michael Keaton, Albert Brooks, and Richard Dreyfuss were all offered the role. With Keaton being too busy, Hanks being under contract for another role, who knows what was going on with Dreyfuss, and Albert Brooks declined over finding the script to be a cheap Woody Allen knockoff, Crystal was there to not only fill the role, but to make it his own.
As for Ryan, she was offered the role and took it. Which makes for one of the best on-screen dynamics of alltime. Seriously, the chemistry and total LACK of chemistry between these two is great. And we are going tobreak down their chemistry in a minute, but first I have to set the stage
So, Harry and Sally just graduated college, and they meet through a mutual friend who ask Harry to give Sally a ride to New York City from The University of of Chicago which is where they went to school. Harry is a sort of chill and carefree guy who likes to make jokes and never takes anything too seriously. Sally is more of a planner with a purpose who knows what she wants and does not like flying by the seat of her pants. In otherwords, they’re two very different people who are not especially open minded to each other at first. And this is kind of it at first. The two have a dinner on the road, they disagree on the notion that men and women can be platonic friends, and they part ways the next day expecting to never see each other again.
Serendipity will get ‘cha
The characters will meet several times throughout the story, and each time at different points in their lives, and self-growth. And that was the first time.
And the way they play the subtle (and eventually not-so-subtle) distaste for each other while also providing a warm charm every dig is truly tapped in. The film was written by the late Nora Ephron whose contribution provided most of the film’s dialogue, with some lines added to the screenplay by Crystal himself. The way the lines are written is clever and sharp while still being grounded and authentic. And the delivery of said lines by these two talents is really special. With Ryan providing an elegant rage and frustration while Crystal whips antagonistic quips with a boyish smirk. It just works so well to establish the bubbling passion that will begin totake shape in their future meetings.

The scene at the diner, you know the one, is a testament to the movies subtle build-up. Sally demonstrates what a fake orgasm looks like in order to challenge Harry’s ability to tell the difference between a real one and a fake one. This scene not only made Meg Ryan an icon, it also made 11 year old boys and grown men everywhere feel things they’d never felt before. Harry’s reaction to this (and the way Sally orders her food in a previous dinner scene) are all telling the audience that he’s being surprised by this seemingly predictable and boring prude former classmate.
Fast forward to five years after their first meeting, the couple are now in their mid-20s and find themselves on the same flight. Sally, now engaged to a guy named Joe, is surprised to learn that Harry is also now engaged.The pair discuss their romantic lives, revisit some old ideas and conversations from their previous meeting, and seem to see a more mature side of each other that once again poses the question: can they REALLY just befriends? Without the guise of petty conflict looming over them, it’s getting harder and harder to ignore that these two “friends” have really never thought about being more than that. Even though they don’t see it because they don’t even consider themselves friends after this second meeting.
Similar to what we all love about Richard Linklater’s masterpiece Before trilogy (comprised of Before Sunset, Before Sunrise, and Before Midnight), we’re seeing these charming characters evolve over multiple periods oftheir lives which introduces new conflicts, new connections, and new feelings. Only instead of a trilogy of films it’s all done over these tight vignettes throughout the story.
Another five years passes, and this time things start to really feel different.
Who says there’s no such thing as destiny?
While browsing a bookstore in the city, Harry and Sally bump into each other once again. This time, they’reboth less youthful and bright eyed about love and the future. They’ve both separated from their respective partners with Harry’s girl leaving him for another man and Sally had simply realized that Jo wasn’t for her.The duo get coffee, catch up, and discuss their bad luck with life and how that’s affected the way they think about relationships. This creates a bond between the two. Sally finds herself unsure of what she wants for the first time ever, and Harry finds himself longing for the right woman to fully commit himself to. It’s like over time the huge gap between these two started to close. Sally comes down from her too high expectations and Harry comes up from his basement level life ambitions. They meet somewhere in the middle on steady ground to really see each other.
This all culminates in a New Year’s Eve party where the two share a very uncomfortable midnight smooch. This leads to nothing as the two continue dating other people but remain friends. And from here on out, there are no parting ways and reuniting five years later. They have ups and downs in their relationship as pals. But they do remain friends. And just when we think men and women can sort of exist as platonic homies, Sally finds out that her ex is getting married, which kicks off the turning point when Harry goes to her apartment to comfort her and the two end up having sex and breaking the boundaries of their entire decade long dynamic.
And again, the actors have to play this spectrum of emotions to really make us believe it. We need to buy the fact that they were enemies, slowly became friends, then found their way into some sort of romantic interest (even if it seemed fleeting) and now we need to believe the awkward wedge in their relationship after sleeping together is about to undo them entirely.
Finding themselves unable to move past the sex, Harry and Sally decide that there’s no way to go back to the way things were. They can’t stay friends because things have gotten complicated. So they part ways again. Until…

New Year’s Eve, 1988, 11 years since the two met. Sally misses her friendship with Harry and sees the holiday as a nostalgic memory that makes her long for conversations with her quirky and witty friend. Harry is drowning his sorrows walking around the city and lamenting his lost love when the two meet again. This time there’s no debate, no difference of opinion, no holding back. Harry and Sally are in love and they aren’t about to pretend that what they’ve spent over a decade creating is anything less than that, and they get married, proving once and for all that men and women CAN’T be friends?? Huh… weird.
Hell, my wife and I started as just friends and over time we came to see each other differently and now I’ve been happily married for almost ten years so ya never know.
And since this movie’s release, the characteristics of Harry and Sally have inspired so many movies that they’ve become tropes and even cliches. This movie was sort of revolutionary for the genre as it’s hard to not find its DNA in every other movie like it. But none have done it quite as delicious as this movie and I’m so glad I got to watch this after covering The Talented Mr. Ripley last week because that movie gave me the opposite reaction of this one.
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