The romantic comedy genre is essentially as old as cinema itself, having existed in various forms since the days of Buster Keaton and silent films. In the 1930s and 1940s movies like Frank Capra’s It happened one night (1934), by George Cukor The Philadelphia Story (1940) and that of Michael Curtiz Casablanca (1942) expanded on these stories and elevated the subject matter, introducing many of the genre conventions that would become commonplace: love at first sight, whirlwind accelerated courtship, love triangles, sweeping romantic gestures, etc. Slapstick romcoms such as Raising baby (1938) and His girl Friday (1940) helped develop the genre even further, putting the female character in the lead role and putting more emphasis on comedic elements. In the 1950s, legendary director Billy Wilder carried the torch by crafting luscious romantic comedies in technicolor to showcase the icons of the golden age: Rock Hudson, Clark Gable, Cary Grant, Humphrey Bogart, Audrey Hepburn, Gary Cooper and of course Marilyn Monroe.
In the 70s, like movies Harold and Maud (1971) and Annie Hall (1977) pushed the boundaries of what these films could be. They portrayed convoluted romances, often focused on struggles in adjusting to evolving gender and identity politics. Albert Brooks’ Modern romance (1981) and Sydney Pollack’s Tootie (1982) cleverly lifted these ideas to the level of parody, as modern classics like broadcast news (1987) and hit by the moon (1987) built on the successes of the progressive style of the 1970s with great success. It is useful to understand When Harry met Sally…(1989) in the larger context of romantic comedy, as it essentially set the standard for the genre forever. Directed by Rob Reiner and written by rom-com royalty Nora Ephron, the film suggests and then rejects clichéd genre conventions, and it deftly weaves in discussions of gender politics that double as its punch line. And because it’s written by a woman, it offers arguably the most complete romantic portrayal in movie history.
A fateful encounter
Harry and Sally meet in 1977 on the last day of school. They have arranged through a mutual friend to drive from Chicago to New York City as they both begin their postgraduate lives in the East. During the ride, they argue over various topics, including the film’s central question; can men and women be friends without sex getting in the way? These discussions turn into passionate arguments and by the end of the ride they are at each other’s throats. Once they make their way to New York, they separate. The plot is already starting to undermine the expectations of the genre. It’s nowhere near love at first sight. The film doubles down on this subversion, as the two meet again five years later on a flight and again decide not to be in each other’s lives. Another five years pass, and they run into each other in a bookstore, and the movie begins in full.
Harry and Sally begin spending time together as friends, eventually rejecting the idea that it’s impossible. They go out to dinner together, visit museums and talk on the phone late at night Casablanca. They bond as friends by commiserating with their own romantic failings, and unlike many films of the genre, they are able to do so without any kind of outside pressure. No toxic love triangles; no major ethical dilemmas like those of Nora Ephron’s later film You’ve got mail (1998); no jealous exes trying to foil their relationship. The only thing stopping the two lost souls from being together is their own stubborn personalities and ideological differences. One night, Sally learns of her ex’s new engagement and calls Harry to her apartment for comfort. That comfort turns into sex and their innocent friendship is forever changed. They cannot reconcile this new development at first, causing them to fight and become distant. But then. of course, in a move that has now become rom-com 101, Harry delivers an age-old romantic monologue, and the rest is history.
Talk in circles
The main achievement of When Harry met Sally… is how it holds the viewer’s attention to mostly dialogue alone. Like the ones mentioned before Ann Hall, this film mainly contains conversations: walk-and-talks in the street, debates in the car, chats during dinner, long telephone conversations. These conversations provide plenty of room for discussions of gender politics and Harry’s clever barbs. But unlike the Woody Allen movie, the script is able to speak faithfully from the female perspective. In the opening car scene, they have their first fight over gender, in which Harry states that men have darker inner lives than women. He insists that he constantly think about death, which will better prepare him for the inevitable. Sally easily pokes holes in his logic and replies that he will spend his whole life worrying instead of actually living. In the now-iconic scene in Katz’s deli, the two discuss a woman’s ability to fake an orgasm. Sally puts it back in place and gives her best imitation to show him how hard it is to tell fake from real. The scene also features the film’s most iconic gag, when a nearby woman tells her waiter, “I’ll have what she’s got.”
The Casablanca scene probably also offers another conversation where Sally reveals the simplicity of the male brain. As they watch the movie, Harry explains that there are two kinds of women; high maintenance and low maintenance. He sees Sally as a maintenance man because she has her own way of ordering her meals – dressings and sauces should always come with it. She decides to go to bed, and Harry says he’s probably too miserable to sleep, so he stays up all night moaning. He lets out a series of moans and stares blankly off into space. Meanwhile, Sally hangs up, takes a deep breath and turns off the light. This juxtaposition feels completely intentional; Sally is able to calm herself down and go to bed, while Harry sits there moaning like an emotionally inept zombie. It is played for comedic effect, but it also illustrates a deeper point. Sure, Sally might be obsessed with the way she orders salads, but Harry is such an immature wreck that he would rather whine all night than just take a deep breath and rest.
A modern romance
Having this series of probing conversations before they’re even romantically engaged allows the couple to strike a solid middle ground before sex is even involved. And in that way, the movie still feels impressively modern, even by today’s standards. This device would be expanded upon in Richard Linklater’s Masterful Before the dawn trilogy in the 90s and 2000s. In a similar way, actress Julie Delpy was able to contribute to the script to better reflect the female perspective. Like the Before films, Sally’s autonomy and ability to vouch for the female perspective in all of these debates serves to contemporary the narrative in 21st century gender politics. Harry’s somewhat archaic understanding of women is ultimately a major part of his folly. For all of Harry’s fatalism and kvetching, his humor serves as his main draw throughout the film, not his ironclad understanding of gender politics. And ultimately what endears him to Sally is his maturation in the decade since they met.
In that fateful first conversation in the car, Sally says she wants to go to New York City so things happen to her – so she can meet people and have experiences and be someone. The ever-sardonic Harry suggests a dark future: “Suppose nothing happens to you. Say you live there all your life and nothing happens; you never meet anyone; you never become anything, and in the end you die…’ Harry’s snippy appearance suggests he’s got it all right and that Sally is the naive one. But the events in the film turn that whole world view upside down. It is Harry who must go through a decade of trials and tribulations to understand how to live.
He has to learn the hard way that his perception of women, and of life in general, is fundamentally flawed. And only when he is ready does he fully deserve to love her and be happy. It is then that he realizes, as shown in the beautiful finale of the monologue, that her idiosyncrasies and diverse perspectives are what make her so interesting to him. The couple really falls in love in these last moments and skillfully postpones gratification until the last possible moment. There’s no denying that romantic comedies have proliferated over the past few decades When Harry met Sally…but most of them seem to miss the point of this film so skillfully made over 30 years ago.