when harry met sally

When we met Harry and Sally

Whenever great movies come into conversation, When Harry Met Sally hits the tongue.  I’ve been happily surprised that younger generations continue to be not just aware but big fans of the movie.  So, what exactly made this movie insanely successful, universal and timeless?  With at least 4 wins from 16 nominations (IMDB), from 9 different categories, the answer is craftsmanship in every aspect of film making.


Nearly all great films start from the same seed – a great script.  Born into a family of writers and with earnest efforts in journalism early on, Nora Ephron had many great works, however it is this script that earned her an award.  Germinated in a conversation with Rob Reiner, Andrew Scheiman and Ephron, the study of relationships was inspired by life experiences and the “he said-she said” nature of the conversation (TCM).

She took classic gender roles all-in, from expectations from first-dates and after sex, to concerns when the break-up may come, be it why and when the breakup was decided (and when Mr. Zero knows before you do), or which furniture makes the cut in the shared abode (so, not the ROY ROGERS GARAGE SALE COFFEE TABLE) or how to best plan for an eventual break-up (put your names in your books).

Ephron’s writing itself is brilliant, from the immensely quotable one-liners to the zooming in and out of the moments in Harry’s and Sally’s lives as they grow and mature. “Ephron’s dialogue represents the way people would like to be able to talk. It’s witty and epigrammatic…” (Ebert’s 1989 review) Life events, like their respective break-ups, force our protagonists to grow and develop a space for them to have more than an acquaintance’s level of interest (like on that drive from Chicago to New York).  But it is more than simple narrative stops through a lifetime, it’s looking in and around these moments from different perspectives.   As Steve Axelrod shared in a writing group conversation (Go Into the Story), several years ago, Ephron was skilled at using multiple contexts of a single scene to add depth.

Ephron goes beyond simple typical gender roles, though, and includes two souls of different ages with wildly different perspectives on life – Sally with her optimistic even if a little passive even in her pragmatic approach to happiness, and Harry with his war-worn pessimistic view in waiting for death.  We see the evolution of Sally through her change in comfort of sex topics, moving from the first café embarrassed comment about having great sex, to the full display of orgasm.  Not to be left unmentioned is her change in position on Casablanca, the romance given the nod and strength of foundation for timelessness – which at first was that Ingrid Bergman was very practical and made the right choice, to later denying this position.  We see Harry soften over the years and expose more and more vulnerability (I mean, he didn’t just sing on the karaoke machine in the Sharper Image, but bought one to serenade Sally over voicemail).

The story is a fine blend of three different buddy films – that of Harry and Sally, of course, but also between each of them and their best friends of the same sex.  Each member of the three pairs, with their own endearing quirks and mannerisms, isn’t as good alone as with the buddy.  Since Harry and Sally are also our dual protagonists, Jess and Marie are the more stereotypical buddies; each have even lesser skill than Harry or Sally, but are forever supportive (OK, minus ignoring the request to wait to call the other after the blind date gone sideways! But, at least they asked first and hey, it was love.).

But is the main story a buddy film? After all, the question is posed – can men and women even be buddies?  Writer and actress Rebecca Gethings agrees it is fitting as a buddy story.  and she along with relationship expert Judy James, agree that where men and women friendships exist, a majority of them include one who harbors romantic feelings for the other (BBC).

One of Ephron’s genius skills was the ability to take simple human nature and incorporate in scenes.  The transition of a fun karaoke scene to one of embarrassment when the audience changes, acting appalled when someone can’t remember a name that we ourselves strained for, saying I love you in reaction to a feeling of jealousy.

The use of the holidays again is effective in helping the story have a familiar and timeless feel.  As does watching characters try to get over someone, deal with aging and realizing that familiarity breeds affection.

I’ve heard it said that the best films include a line of dialogue that tell the story in one line, and this meets the mark:

“You realize of course that we could never be friends… men and women can’t be friends because the sex part always gets in the way” – Harry


It’s nearly impossible to imagine anyone besides Billy Crystal and Meg Ryan in the lead roles, isn’t it? Receiving many nominations for acting, I’m not alone in knowing these were great performances; from their comedic timing and vulnerability, to key additions to the dialogue (most notable the “I’ll have what she’s having,” suggested by Crystal) and the palpable chemistry.  But they weren’t the first choices; can you imagine if Albert Brooks and Susan Dey (Mental Floss)? We’ll never really know if they would have crashed or sored in these roles, but I do believe the casting turned out exactly as it was meant to be.


A classic choice in New York City, a town where we expect Harry will fit right in with his disposition and career ambitions, but we aren’t initially sure about Sally. As we see Sally change throughout the film, it makes sense that the city was part of that influence. She’s a little tougher and even funny as the story progresses.    The airport as a logical run-in location, for two career folks in a big city, and a book store for two educated people to collide – it all resonates.  And the real stories from couples? Delivered in a classical environment with traditional furniture and romantic wallpaper.


Perhaps most immediately evident is the use of the screen space to add a layer to the story.  As Jesse David Fox makes most clear, the physical distance between the characters tells us how connected the pair are at the given point of the story (Vulture). They get closer over time, until the major conflict which drives them back apart. There is also effective use of the split screen, used multiple times, pitting them together or apart in parallel time.

Perhaps one of the more interesting tidbits in Director choice is the fact that in the first script, Harry and Sally did not end up together, but Reiner insisted (Mental Floss).

He also switched from using the real couples of the married tales to actors relaying those true stories.  These stories were dynamic, ranging from simple to complex.  The actors even stayed true to the various ways couples talk – finishing sentences, talking over each other, one chatty and one quiet.

A fine director also pushes scenes to their full potential – Reiner acted out the orgasm scene to demonstrate to Ryan how dramatic the display needed to be for it to work.


The Director choice to use standards, but with a fresh musician who brought is own style, reinforced the film’s timeless quality without making it feel immediately dated (TCM).


Lest you think there aren’t wardrobe choices for an modern-day movie (as opposed to a historical or mythical context), review Elle’s excellent explanation on the explicit choices around Sally’s hair, clothing and accessories for every scene; the most dramatic effect in the buttoned-up prudish outfit warn in the orgasm scene.  Harry’s wardrobe, too, reinforces his place in the relationship and ties to the city.

Is nothing wrong?

I would be remiss in writing a piece on this movie to not take the change to talk about one, if not the only, thing that drives me crazy about the film.  It’s this scene at Jess and Marie’s wedding:


Why can’t we get past this? I mean, are we gonna carry this thing around forever?


Forever? It just happened!


It happened three weeks ago. You know how a year to a person is like seven years to a dog?


Yes. Is one of us supposed to be a dog in this scenario?




Who is the dog?


You are.


I am? I am the dog? I am the dog?


In my opinion, it seems like Harry should be the dog, not just for the typical men-are-dogs commentary, but because for him the time seems longer.  So three weeks in human time is like 21 weeks in dog time. So clearly Sally was right, Harry was the dog!

Have you ever thought how different this film would be today? Well fear not, someone has already considered this (ABC News).

What do you think? Is there another reason to love this movie? Let me know in the comments.



This article covers a great point or two about forging a different path for the romcom:


Learning by Example

People have a variety of methods that they use to familiarize themselves with the unfamiliar. For me, my first step is often seeing how others have done it. Screenwriting has been no different.  I choose to read scripts for movies that I’m fairly familiar with.  Here I will describe the hard copy screenplays in my library (I have dozens more in soft form, more on this later), and what lead me to plucking them out of the script bin for study.


These are listed in no particular order, only categorized with a quick snip of the category and the reason I thought the example was relevant. You’ll see some entered in more than one category.

These stories have some interesting aspect to them with regards to the story timeline.  For example, Ocean’s Eleven. If you don’t already know, this is a fun heist story where the audience follows along curiously about how the crew will pull it off given the comprehensive security around their target. After recruiting for all of the different roles, it is revealed that the leader, Danny Ocean, isn’t just in this for the loot – he wants revenge and to win his ex-wife, Tess, back.  After convincing the crew that this won’t jeopardize the operation, the heist gets back underway.   The reason I loved reviewing this script for timing was that  the key part of the movie – the heist itself – takes place over just a few minutes and is done without completely confusing or losing the audience. I thought this was a rather interesting writing challenge.  Similarly, I’m looking at these scripts for timeline challenges:

  • Pulp Fiction – This asynchronous audience-puzzle of a story is a clear example of owning the story timeline and laying out in a clever and entertaining way.
  • The Hangover – A fairly recent story showing how to handle backtracking through a series of events without cheating the audience with an obvious outcome.
  • The Social Network – The story itself is told in a straightforward way in terms of the story timeline, but the audience has knowledge of some of the history here and would be watching for the timeline to jive with their knowledge (or fill in holes, but certainly not conflict). I think that creates an interesting constraint on this script.
  • The Bourne Identity – In this story we take the issue of a dual-past to be uncovered and teased apart all while under immediate time pressure.  Handling these two vectors in one story is challenging.
  • When Harry Met Sally – This story takes place over some 15 years. It was important for the offer to allow the time pass to be believable and not a short cut to the characters’ development.

Romance / Romantic Comedy

Being my primary genre for writing, I picked a few well-loved examples. Most stories have a romance plot or sub-plot, but the light-hearted romance is as difficult to write as a complex song in Major keys.  The first is listed often not just as a popular romance but as the best written movie of all time. I think romantic comedy is especially challenging because there is an audience mandated outcome, yet that outcome must be delivered in an unexpected way.

  • Casablanca – A classic tale. Can you choose to not be with your love for a greater purpose? Are there different types of love?
  • When Harry Met Sally – There are a few questions that might be answered here – Can love grow over time? Is it ever too late to be more than friends? Opposites may attract but can it work long term? Can women and men be ‘just’ friends?
  • You’ve Got Mail – This one is not only in my library because it’s a great romantic comedy but it incorporates modern technology and the challenges not only for the characters in meeting in person but also for the writer to not bore the audience when technology is being used.


What’s great about the Ocean’s Eleven script – and I would love to see the original script to see if this was something carried forward or recaptured –  is that it has an old style dialogue, especially between Danny and Tess.  One of my favorite sections of dialogue is in the restaurant when Danny approaches Tess while she waits for Terry. I started to put a snippet here but I think I’ll wait for a full post on the script for that.  It’s for similar reasons I love Casablanca.  Prime examples of accomplishing the most bang with the fewest words. It’s an art, for sure. When Harry Met Sally also features some simple and effective dialogue. I think they call this efficient dialogue in writing circles.

Character Development

The following are a mix of genres but all present a fantastic exploration into one or more characters. Some even surprise us in the end – for example Ferris, seemingly a teen punk, and may normally be, but in this story a caring friend who just may have saved his friend, Cameron.  Others feature every-day people that help us learn or once-again recognize something about ourselves.

  • The Best Exotic Marigold Hotel – The general study of older characters in later stages of life and relationships – tolerated and forbidden.
  • The Silver Linings Playbook – A ground-breaking appropriate humanization of extreme personalities.
  • Sideways – The joy of finding someone who can look beyond the cover of a person who has a lot to offer and does not even realize it himself.
  • Napoleon Dynamite – Really a time period piece but also the complexity of what seems simple.
  • The Breakfast Club – Everything is relative and deserves perspective. These reps of various walks of life exposed and finding common ground is a beautiful mental watermark for the audience.
  • Ferris Bueller’s Day Off – The child of absent, demanding parents has to be rescued from despair by a trouble-making friend with good intentions if with risky methods.
  • It’s a Wonderful Life – I watch this movie every Thanksgiving. This classic helps us recognize the impact we have had even when we currently feel like a failure or that life is too unfair to bear.


I never appreciated good comedies more until I tried to write comic aspects into my script. I’m still trying to address comments that my story needs to be ‘funnier’!

  • Wedding Crashers – Chalk full of several types of comedy, a great example and often quoted movie.
  • This is 40 – A recent addition which has few dramatic lines but the ability to pull in things that suck about being middle-aged (I am well aware at present) without being cliché is fantastic
  • Office Space – Another case of brining things out of the office experience that drive us all nuts in a hilarious way
  • Swingers – Probably primarily a favorite because I know it was early work of Favreau’s, more subtle humor and humor in characters

A few others already mentioned like Ferris Bueller’s Day Off and The Hangover, are good to study for their comedic elements as well.

I hope this has helped trigger some ideas for movies to look study for certain aspects of screenwriting.  Next I will blog some great sources of scripts that I have found.