When Harry Met Sally… (1989)

Starring: Billy Crystal, Meg Ryan, Carrie Fisher, and Bruno Kirby
Grade: Classic

“I came here tonight because when you realize that you want to spend the rest of your life with somebody, you want the rest of your life to start as soon as possible”.

That is poetry.

Summary

*Interspliced scenes of old couples talking about how they met, and the details of their relationships are included in-between scenes of the main story.*

Following graduation at the University of Chicago in 1977, Harry Burns (Crystal) is making out with his girlfriend Amanda, as her best friend Sally Albright (Ryan) drives up. She is driving Harry to New York because she’s going to start journalism school, and Harry is starting his career there. Harry says goodbye to Amanda and heads out with Sally on this long, 18-hour road trip. Right away, we see the stark contrast between the two. Sally is optimistic in her future, even though she has nothing specific going on in her life, and Harry seems to work extra hard in irking her with his pessimistic outlook on things. They discuss everything and anything on the way there, including if Ingrid Bergman made the right decision in leaving Humphrey Bogart in Casablanca. Sally says she did, so Harry chalks this up as her not having life-altering sex like how Rick Blaine clearly gave Ilsa. Stopping at a diner, this conversation continues, as Harry asks more about her personal relationship struggles. As this goes on, Harry’s straightforwardness and opinions on relationships and friendships really turn her off to his personality. After he mentions she’s attractive, she gets offended because she thinks he’s coming on to her, even though he insists he’s not. He just mentioned it as more of a passing statement. Then, it gets worse. Back in the car, one particular conversation goes off the rails. Harry argues that a man and a woman can never be friends because “the sex part always gets in the way”. They argue this back and forth, but Harry has a counterargument for pretty much anything she says. Eventually, they agree they’ll never be friends based off of Harry’s criteria. Once they get to New York, they part ways as awkwardly as possible.

It’s very clear that this was unpleasant for both of them, and they have no interest in seeing each other ever again.

Five years later, Harry runs into Sally and her boyfriend Joe (Steven Ford) at the airport. Harry is now with a small firm as a political consultant. He recognizes Joe but can’t seem to put his finger on Sally. Even so, they talk about their lives before Harry heads out for his flight. Sally is very thankful Harry didn’t remember her, as she vividly remembers him and tells Joe about how awful their drive was five years previously. She also mentions Harry’s theory about men and women not being able to be friends, which results in Joe admitting he doesn’t have any female friends of his own. Following this, they say “I love you” for the first time, and Sally is elated. Next, she gets on her flight. After she orders a very specific Bloody Mary similar to how she ordered a pie at the diner years ago, Harry, who is on the same flight, finally puts it together to the annoyance of Sally. They start talking, so the guy sitting next to Sally gives up his seat for Harry. They catch up on things, with Harry correctly deducing she has only been with Joe for a month (he guessed three weeks but still). He’s much more pleasant this time around, though he still bothers her because of his other philosophies on relationships and sex. Regardless, he reveals he’s getting married to a lawyer named Helen Hillson (Harley Kozak). She’s keeping her name, which is never a good sign. Once they land, Harry asks Sally if she wants to go to dinner as friends, but she reminds him of his old rule about friends that is the basis for this entire film. He says this is an exception because they’re both involved with someone. Though when he thinks it out, he realizes this isn’t possible either, reverting back to his initial rule. Even so, he still wants to go to dinner.

Sally refuses and walks away.

Another five years pass, and Sally is hanging out with her two best friends Marie (Fisher) and Alice (Lisa Jane Persky) at some restaurant. Marie is involved with a married man, and it’s not going well because the guy won’t leave his wife. Alice is kind of irrelevant. Marie and Alice talk about how good Sally has it with Joe. Sadly, Sally reveals they just broke up. Marie tries to set her up with someone, but Sally just wants to wait at the moment. It also doesn’t help that the guy Marie wants to set her up with is someone she set her up with six years previously. The other person Marie suggests has been married for over a year. Meanwhile at a football game, Harry tells his writer best friend Jess (Kirby) that his wife just left him for some tax attorney. Later at some bookstore, Harry runs into Sally once again. They end up bonding over their failed relationships and talk about it some more over coffee, with Sally going in-depth about how everything fell apart with Joe. Following this and an apology from Harry for his behavior towards her years back, they officially decide to become friends, with Sally asking him to dinner. Harry accepts, saying she may be the first attractive female friend he’s ever had that he didn’t want to sleep with.

However, as time goes by and they get closer and closer as best friends, Harry’s theory on friendships between a man and a woman is put to the test.

My Thoughts:

There are two movies that are looked at as the blueprint for the romantic comedy genre, the standard in which every romantic comedy tries to reach. They are Woody Allen’s Annie Hall and Rob Reiner’s When Harry Met Sally…, which is arguably Allen-lite. Very few films have captured the hearts of generations without the backing of big budgets, muscle-bound stars, and science fiction extravaganzas quite like these two. This is the genius of When Harry Met Sally…. Purely focusing on adult relationships and friendships through the years, combined with an impeccable blend of chemistry between our stars, excellent writing and dialogue, and heartfelt but also comic directing, When Harry Met Sally… is one of (arguably the) greatest example on how to flawlessly execute a romantic comedy that is realistic, funny, insightful, warm, and entertaining from start to finish.

Besides the magnificent chemistry between our co-stars, the real champion is screenwriter Nora Ephron, with her screenplay being in the discussion for “greatest ever”. Sincere, lifelike, thought-provoking and above all else, supremely funny, Ephron writes us a romantic comedy that is equal in terms of entertainment value and being an authentic look on the pitfalls of relationships, friendships, and the line between them. Everything is rooted in the classic question of if it’s possible to be best friends with the opposite gender without sex getting in the way. Can a man and a woman be just friends? No film has highlighted this question better than this one. Now, we see it in virtually every romantic comedy, but there hasn’t been a single one that represents the details quite like Ephron does here. If you ask most people this question off the bat, chances are they will give you an immediate answer of “Yes” and balk at any other suggestive possibilities, but When Harry Met Sally… is all about bluntness, giving us the most honest look at this question never seen before on film. Ephron, accurately writing from the male perspective just as she does for the female perspective (a rare feat for screenwriters), has Harry point out that it’s not possible because men think about having sex with any woman that they find attractive. In fact, they even think about having sex with the one’s they don’t find attractive. Sally responds with her bright-eyed and assured confidence that she has plenty of male friends where this isn’t true. Without missing a beat though, Harry explains she only thinks she does. Truthfully, they all want to bang her. It’s just not on the table on her end.

He flat-out says, “…No man can be friends with a woman that he finds attractive. He only wants to have sex with her”. This isn’t a takedown on the male point of view written by a female. This is a statement by a screenwriter who has clearly observed this through years of watching and listening to her peers interact. Is this statement made by Harry awful, juvenile, completely immature, and outrageous? Yes, but do men think like this whether they intend to or not? Also, yes.

People may refuse the truth about how men approach friendships with women until they are blue in the face, but the ones who do argue it are already in a relationship, and the other half are women who tend to speak exactly how Sally does. For better or worse, Harry’s point of view, despite how it bad it makes us all look, is completely spot on. Argue the details all you want, but he’s right in that with true friendships between both men and women, sex will come into one or the other person’s mind in one way, shape, or form. Whether they act on such thoughts is a different thing, but it crosses everyone’s mind. However, everyone lives by the unwritten rule of not admitting this, especially in front of other friends because of the uncomfortable responses it would garner. Nora Ephron puts this theory to the test and admits the truth through the Harry character, making him unlikable to a relatively normal character like Sally but witty to the male audience. It’s absolutely genius writing and scenes like this prove it, shining a light on everything we’ve all unofficially agreed to not talk about. Above all else, this is the legacy of this film. The same goes for Sally telling Harry that women fake orgasms basically so the male ego isn’t hurt. On top of being one of the most memorable scenes in the history of cinema, it talks about another unwritten rule on the female side of things. This alone makes men question everything they know and was something that wasn’t really discussed back then, especially in movies. Now, it’s commonplace to openly discuss every detail of relationships and sex in film, but When Harry Met Sally… was the first film to really break the mold.

It’s because of how honestly it was written.

All of it is rooted back to the late Ephron, a rare screenwriter who understood how to bring these topics to light for a mainstream film, making it seem intuitive and funny rather than something vulgar or offensive. Along with this, every joke, moment, and scene meant something. When Harry Met Sally… is one of the very few films you can look at and say there was no time wasted at all. Every scene, even one’s that involved humor, were carefully crafted to show us where the characters are at in life, how they act around certain people, and how they are in their friendships. How many times do you watch a movie and think to yourself, “That scene was pointless”. Not once does this thought cross your mind here. At most, you can argue that the interspliced scenes of old couples talking weren’t necessary, but I think it fit with the theme of the story and its overall sweet nature, while being used as great transition pieces since so much time passes in the film. Plus, it was a cool little element to differentiate the film from a genre full of similar movies.

The dialogue is about as witty and developed as any Woody Allen, “neurotic New Yorker” film, but it’s much easier to digest for people that have had too much of the famed filmmaker’s style. Instead, we get the easygoing charm and effortless comedic ability of Billy Crystal, matching up with the cute and kindhearted Meg Ryan. Together, things blossom from hated and unwanted acquaintances to a loving friendship where they don’t know what to do without each other in their lives. Despite this being the only time these two have teamed together in a film, they gave us one of the most well-matched co-stars in the genre’s history. Isn’t it crazy to think that they never tried to replicate the magic these two had? Yes, Tom Hanks is Ryan’s best dance partner in rom coms by default, but this isn’t really fair. They got to do three movies together (Joe Versus the Volcano, Sleepless in Seattle, and You’ve Got Mail) compared to Ryan and Crystal doing just this one. Even so, the discussion is closer than you think. They are that special together. What’s different with Hanks and Ryan is that their characters both seem like genuinely good people from the start. Then, they ease into a relationship because of their easygoingness in person, with only circumstances stopping them from making things more pinned down. Here, Harry and Sally are clear opposites in every sense of the word, and they hate each other to start off (more so on Sally’s part) because of their clear philosophical differences in life. Crystal’s Harry challenges Ryan’s Sally but also invites her to join in on the fun, which she isn’t initially into because of her own beliefs and refusal to hearing things out in the straightforward manner Harry presents them.

Harry’s quick-witted responses and intellectual approach to how relationships work is enough to frustrate Sally while entertaining us, but you also see why Sally is put off by some of the things he has to say, especially because he hasn’t truly experienced much in life, though he thinks he has. Not only is this a realistic character trait for any recent college graduate, it’s also a great foreshadowing for the rest of the film.

A song like Louis Armstrong and Ella Fitzgerald’s “Let’s Call the Whole Thing Off” could not have said it any better. Harry and Sally couldn’t be further apart from each other in terms of personality. Sally is an optimistic, reasonably private person who is a little uptight, and is very particular in her style and approach to life. Harry is laidback, comfortable in who he is and what he believes, and doesn’t seem to mind angering others with his “I’m right whether you like it or not” attitude. As the years tick by, the core values of the characters remain, though it becomes more and more faint as time moves on. Once they start to loosen up on certain details regarding their headstrong personal thoughts, this makes their eventual friendship possible. Because of this, they learn from each other and how the opposite sex may think. Since the pressure of sex is taken out of the equation, Harry’s close-minded opinions towards women are opened, as he starts to see the female perspective on things, something he never considered before. This is where we see how much divorce has changed Harry, the funny Chicagoan who was very confident in everything he believed in regarding women and relationships. However, in a short five years, his wife fell out of love with him from right under his nose. In fact, she questions whether she ever loved him. Harry’s world comes crashing down as he moves back to single life and runs into Sally at just the right time.

As Harry, Billy Crystal is just as funny as ever but is also able to put together a well-rounded performance. We know he can do comedy better than most, and his comic acting ability, with quips abound and an ability to let out digging comments that still make him likable, despite the sarcasm being potentially offensive, is arguably at its finest. However, Crystal impresses a lot as the broken man going through a divorce, replicating what his real-life best friend Rob Reiner went through with filmmaker Penny Marshall. Though his humor is still there, Harry is much more cynical in his responses following his divorce. Here, he doesn’t have the usual Crystal enthusiasm we are used to with his onscreen persona. He flashes it here and there when it’s needed, but the character of Harry experiences a lot more trouble than usual in his personal life, so Crystal’s acting and humor respond in kind, representing the feeling of someone going through this period in their life quite accurately. Despite Harry being at his all-time worst in his personal life, he needs this to become the best version of himself. Oddly enough, it’s at his biggest low where he is at his most likable. He becomes more personable and is a lot friendlier. Because of this, Sally is willing to hear him out a bit more and become friends, despite knowing him at his worst and refusing this idea before. This was the intention with Harry, being the typical know-it-all male coming out of college to jaded divorcee. He needed to be brought down a peg. He needed to struggle mightily to succeed, and it was executed perfectly, with Sally being the reason he was able to get out of his funk.

At the same time Harry’s relationship falls apart and they run into each other, Sally’s relationship ends too. Yes, she has handled the news much better than Harry has, but the fact that both of them are in the same situation as single people, despite all the promise they both had years ago, shows how much in common they have as friends. It also seems like fate has come into play. For the first time since they met each other, they can finally understand where they are coming from. By being more open and honest, they can both benefit by talking to each other about the intricacies of men and women through communicating and using this approach in their own lives. This is where the fun begins. The additional fun is them not realizing how well made they are for each other, despite their differences. Though this is a romantic comedy staple, everything else is done so well that we don’t groan at these “expected” parts, they are actually welcomed. The audience wants it and sees it when the characters don’t, especially as we start to see how much Sally reveals to Harry compared to her female friends. This is exemplified in the breakdown she has after hearing about Joe’s marriage. It’s important because it’s the first time you see Sally really show this side of her but once again, she can only explain how she truly feels to Harry.

Everything seems fine in your life until you see your ex succeed, right? This can break anyone.

Obviously, they don’t see how perfect they are for each other at first. As with most adults, you may not see the potential when you are younger but have to take a second look at things as life progresses. You have to grow as people and experience life, different personalities, and different situations. As you do this, you build character as a person. Challenges in real-world circumstances show you who you are and what you are made of. As we can see, Harry and Sally both think they know everything when they are college-aged and are a lot more stuck in their ways. After the first five years, we see how both of them are successful, their personalities are relatively similar, and because of this, their attitudes are reinforced because of where they are at in life. Then, the next five years happen, and this is where it all comes crashing down. These are the challenges we speak of that make-or-break us as human beings and prepare us for the next stage of their lives. Harry and Sally were destined to see each other again whether they ended up together or not, simply because of how badly they needed each other to figure out how to move on. In addition, they both needed to realize what they did wrong previously and find out what they now want. They were there for each other to pick up the pieces of their lives and this is how their friendship develops, with Nora Ephron’s writing making it all the more relatable and the progression of the story being pristine in quality and realism.

Complimenting it is the outstanding performances from both of our leads. Meg Ryan in particular shows us why she was one of the biggest stars of her generation, with an all-around performance encompassing what it means to be single in your 30s, not understanding how men seem to approach long-term and short-term relationships, and when the right time to settle down truly is.

The scene in which she explains why things fell apart with Joe was an early insight into the talent Ryan was. Moving away from the funny stuff for a bit, she talks about how initially, her and Joe wanted the same thing – no marriage. They liked the spontaneity of what they had and not having any commitments with children. However, when she was babysitting for Alice’s kids and played “I Spy” with them. One kid said, “I spy a family” after seeing one, and she started to cry, realizing she’s leaning closer and closer to wanting this in her life. Additionally, which also doesn’t seem to be pointed out enough, is that though couples who argue they don’t want kids very rarely take advantage of not having anyone else in the house. They don’t randomly fly to Rome or have sex on the kitchen floor without a care in the world. Most just live normal, quiet lives and take the situation for granted. The well-adjusted Sally may be the first character to recognize this important fact, giving one of the most bullet-proof arguments we have ever seen regarding marriage and starting a family versus not. Though things were going well with Joe up until this moment, it ended right then and there when he stated he had no interest in it. Seeing how much it affects her personally and how she saves face for everyone is very understated work from Ryan, making her eventual aforementioned breakdown when finding out Joe was getting married that much more impactful.

It hits us like a brick when she realizes the truth:

“All this time, I’ve been saying that he didn’t want to get married, but the truth is, he didn’t want to marry me“.

Though it’s funny to watch Harry and Sally argue and annoy each other in the beginning, the film is at its best when they bond, taking turns being a cushion when the other needs it most. Harry was there for Sally in heartbeat when Joe gets engaged, just as Sally is there for Harry when he runs into his ex-wife Helen and her new husband Ira. Not only does Crystal play the mood swing so well, with the subsequent hysterical blow-up on his friends right after (“I was being nice!”), but the best part is his argument with Sally. They both lay into each other with vicious honesty and air out all their grievances towards each other in the heat of the moment. However, immediately following this, they both come to the adult conclusion of an apology and a hug. If this happened during one of the first two times they met, they probably would have never spoken to each other again. Hell, in most movies today, this would be the turning point of the movie and wouldn’t be resolved until the ending. However, this singular scene shows us how strong they have become as a unit. The bond they create is so real, and the audience feels it to the point where we become relieved that Harry initiates the apology right after they blow up on each other. They’re too strong together. They are the “couple” everyone wants to be friends with just because they complement and play off each other so well. Though they technically aren’t a couple, everyone thinks they should be. The earliest indication of this being the double date with their best friends and it hilariously backfiring, with their dates falling for each other. You just want to scream at Harry and Sally to stop messing around and date already.

Proving Harry’s theories right, you can tell it crosses both of their minds right at that first New Year’s party.

All of this is what makes the second half of the film just as entertaining as the first half.

Along with the insight on relationships and friendships, When Harry Met Sally… is filled with countless scenes that will have you laughing on a consistent basis. The writing is just fantastic. It’s not just the joke-telling either like when Harry quips that when he buys a book, he reads the last page first because if he dies, he at least knows how it ends. There are a lot of hilariously quotable things throughout like this, but this isn’t the genius of the movie. The lines actually mean something and are important to understanding the characters, the way they think, and why they do the things they do, a lost art in modern comedic films. Even so, my favorites had to have been when Sally talks about having “great sex” with a former boyfriend named Sheldon and Harry not believing her (because the guy’s name is Sheldon), the idea of combining the obituaries section of the newspaper with the real estate section, the baseball scene where Harry talks about how his divorce happened with Jess and when they talk, they still do the “wave” with the crowd, and the “paprikash” scene. I have no idea why I love this conversation so much, but it’s something I quote daily from the film.

One of the best romantic comedies of all time and one of the best films of the decade, When Harry Met Sally… shows us that we can still showcase honesty in a romantic comedy and it’s not as cynical as some may think it to be. We also see how a true friendship can help us get through anything in life, along with how going through your lowest of lows can help you reach your highest of highs. Led by lovable, natural, and very funny performances by the chemistry-filled tandem of Billy Crystal and Meg Ryan, an all-time screenplay written by Nora Ephron, and passionate direction from Rob Reiner, When Harry Met Sally… deserves its spot as the go-to romantic comedy film.

Fun Fact: Tom Hanks, Michael Keaton, Richard Dreyfuss, and Albert Brooks all turned down the role of Harry. Molly Ringwald, Elizabeth Perkins, Susan Dey, and Elizabeth McGovern were considered for Sally. Let’s just say, they landed the right people here.