Let’s Talk About ‘When Harry Met Sally…’ (1989)

What When Harry Met Sally Means to Us

It took me a long time to actually watch When Harry Met Sally. I always lumped it in with other romantic comedies such as Sleepless in Seattle or You’ve Got Mail. Not that there is anything wrong with those movies, it’s just that I’m not a particularly massive fan of the genre. But I am a fan of good movies, and When Harry Met Sally certainly falls into that category. I was drawn in from the very start, as the witty, quick script never let up. The chemistry between Billy Crystal and Meg Ryan is off the charts and I was completely invested emotionally by the end. There’s also the diner scene, which is one of the most iconic scenes in movie history and overall it just feels like a very intelligent, well-made film. It’s now something that I watch on regular repeat and would happily say it’s the greatest romantic comedy of all time.

– Lee McCutcheon

I fell in love with When Harry Met Sally as a teen. I had no business falling in love with it. I was into genre movies back then. Sci-fi and action mostly. Shit with explosions. Or spaceships fighting in space. And exploding. I don’t know if it had something to do with how often this movie was on TV when I was an adolescent (it must have been on Showtime, because that’s the only premium channel we had) or if it’s just a testament to how boring life in a small town was that I would give a rom-com a chance as a teen. Whatever it was, I fell ridiculously in love with this movie. To this day I can pop it in and watch it and laugh and be moved during the New Years scene as if it were the first time. When Harry Met Sally not only tops the list of my favorite romantic comedies – it’s one of my favorite films of all time.

Billy Dhalgren


After his 1979 divorce from Penny Marshall, director Rob Reiner set out to make a film inspired by his life as a newly single person, as well as his cynical views on love. In 1984, during a lunch with his friend and screenwriter Nora Ephron, he broached the premise of two people who meet and decide to remain platonic because sex would ruin their friendship. Of course, they have sex anyway and of course, it ruins their friendship. Ephron liked the idea and agreed to write the screenplay. 

While working on the first draft, originally titled How They Met, she interviewed Reiner about his views on women and being single. Reiner was a clinical pessimist and yet insanely funny. From these discussions, the character of Harry was born. For Sally, a highly neurotic journalist with insanely specific food orders, Ephron based a lot of the character on herself and her friends around New York. 

It took years for the screenplay to come together, but during the writing process, Ephron began to structure the dialogue after Reiner’s real-life friendship with actor Billy Crystal. Crystal, who was married with children at this point, claimed he was living vicariously through the newly single Reiner. One of the film’s most memorable scenes, when Harry and Sally are on the phone and watch Casablanca together in their respective beds, is something Ephron lifted directly from Reiner and Crystal real-life relationship.So I suppose one could say Crystal was Sally to Reiner’s Harry?

When Ephron wasn’t feeling motivated to write, she would interview various couples from the production company. Those interviews eventually made it into the film as well, becoming the sweet, hilarious interludes that separated the years that spanned Harry and Sally’s relationship.

“There are certain universal things that men experience and the fact that I was working with Nora Ephron, she brought the female perspective to the mix, and we made it a part of the creative process to say what actually happens between men and women. You know, it’s not about the cute meet or putting some obstacles between the lovers so that they get together, but what actually happens with men and women. That was really the motivation for me. Because I was married for 10 years and had been single for 10 years and I was making a mess of my dating life. I kept saying, how does this work? How do a man and woman get together? I started thinking about that and I talked to Nora and she liked the idea and we started working on it.” – Rob Reiner

Katz’s Delicatessen

In what is perhaps the best known scene in the movie, Harry and Sally enjoy an afternoon lunch together at Katz’s Delicatessen. The topic of conversation turns to sex, and Sally tells Harry that men can’t tell the difference between a fake orgasm and a real one. Given the movie had seemingly focused so much on Harry, Ephron and Reiner felt like Sally needed her own moment to shine. The topic of a fake orgasm was a good one, but it was Meg Ryan’s idea for Sally to literally fake the orgasm in the middle of a restaurant. It’s hard to tell in the finished cut, but apparently Ryan had trouble… er, performing. It was nerve-wracking for her to mimic a – fake – orgasm in front of an entire cast of extras and the crew. 

Reiner apparently felt nerves as well, considering he was directing an orgasm in front of his mother, Estelle Reiner, who was one of the extras. Ryan’s first few takes were lukewarm at best and it was finally Reiner who had to sit down in that iconic booth and show Meg exactly what he wanted to see from the performance. The “Oh god, oh god!” and pounding of the table came from Reiner’s direction. After that, Ryan grew more confident and eventually nailed what is now one of the most iconic scenes in film history. I would be remiss not to mention Reiner’s mother Estelle delivered the equally iconic quote “I’ll have what she’s having”, a line that was suggested by Billy Crystal.

The Happy Ever After That Almost Wasn’t

“I love that you get cold when it’s 71 degrees out. I love that it takes you an hour and a half to order a sandwich. I love that you get a little crinkle above your nose when you’re looking at me like I’m nuts. I love that after I spend the day with you, I can still smell your perfume on my clothes. And I love that you are the last person I want to talk to before I go to sleep at night. And it’s not because I’m lonely, and it’s not because it’s New Year’s Eve. I came here tonight because 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.” – Harry Burns

As the screenplay for When Harry Met Sally was coming together, both Reiner and Ephron agreed that they wanted a realistic outcome for Harry and Sally’s relationship. This meant that two would eventually go their separate ways while remaining friends. For Ephron and Reiner, this was the true ending. It was meant to be very ambiguous. Maybe they ended up together, maybe not. But test audiences hated the uncertainty. From there, Reiner and Ephron had a change of heart and tweaked the script to include the New Year’s Eve climax where Harry finally declares his love for Sally, and all of her many quirks. It probably helped that Reiner had fallen in love again on the set of When Harry Met Sally and thus didn’t mind changing the cynical ending to something more sentimental, providing closure for the characters, and for the audience. 


While When Harry Met Sally had its fair share of critics when it premiered in 1989, it has since become a classic in the romantic comedy genre, and arguably the one movie all other rom-coms are to be measured against. When Harry Met Sally was just another gold star in an already successful directing career for Reiner, and Ephron went on to help write and direct other rom-com classics like Sleepless in Seattle and You’ve Got Mail. Billy Crystal and Meg Ryan’s on-screen chemistry has only been rivaled by Ryan’s chemistry with Tom Hanks. 

It combined so many rom-com tropes, executing them to perfection while bringing both a male and female perspective to the table. Harry and Sally were both fully fleshed out people, flawed and quirky but never crossing the line into pretentious or unlikable. When I watch this movie, I find myself sorely missing Nora Ephron and what she brought to the genre. She seemed to truly understand romance and how to get into the minds of both men and women. Simply put, despite the influx of rom-coms since, there has not been another to reach the same plateau as When Harry Met Sally. And for that, it remains a timeless classic.

What are your fond or romantic memories of When Harry Met Sally…? Do you have a fun fact or piece of trivia on the film? Share it in the comments below!

Author: Romona Comet

"I'm probably watching a rom-com right now."