WHEN HARRY MET SALLY… (1989)

Out of the thousands of romantic comedies out there, I’d swear in front of a judge that When Harry Met Sally… is the best. Few films have captured the ache of romantic loneliness quite so well, nor the fear of ruining an important friendship through being physically intimate with one another. In a character-driven story that perfectly balances romance and comedy, we get to know two people in their search for love.

Of course, it doesn’t start that way. Our lovebirds initially loathe each other. In their first meeting, as they carpool from Chicago to New York, it’s blatantly evident that they’re distinctly different people. Sally (Meg Ryan) is frustratingly compulsive, whereas Harry (Billy Crystal) is crass and untidy. Much like some of the great romantic comedies, our protagonists take an immediate dislike to one another, a feeling they try to conceal during the trip.

This doesn’t work; it takes very little for the pair to start bickering. “Why don’t you tell me your life story?” Harry asks. Within minutes, they’re arguing about whether Sally has a dark side, before moving on to whether Ilsa was right to leave Rick in Casablanca (1941), or if Sally has ever experienced great sex. Their dynamic becomes clear: Harry’s obnoxious behaviour offends, while Sally, what with her slightly anxious personality, takes umbrage, conveying her disdain for everything Harry says, does, or represents.

This isn’t an original set-up: the only obstacle to them falling desperately in love is how much they can’t stand each other. It Happened One Night (1934) immortalised this character dynamic, with screenwriter Nora Ephron even making explicit reference to another classic rom-com from this era, The Lady Vanishes (1938). “You’re the most contemptible person I’ve ever met in all my life!” Iris Henderson (Margaret Lockwood) informs her soon-to-be lover, Gilbert Redman (Michael Redgrave). He smoothly retorts, “Confidentially, I think you’re a bit of a stinker too.”

Men are playfully offensive, flippant, and distasteful, while women are oppressively conceited and compulsively well-mannered. It will take a patient woman to civilise him, and a romantic man to loosen her up. This is a narrative device that’s been used endlessly, but Ephron and director Rob Reiner turn the interactions between Harry and Sally into a unique conflict through wonderful characterisation.

Firstly, Harry is a deeply pessimistic person. Finding it impossible to be cheerful, he takes pride in his cynical demeanour, as though it were a badge of honour and not a deep-rooted neurosis. His tendency to read the end of a book before he finishes it exemplifies his tragic big-picture perspective: “Look, when the shit comes down, I’m going to be ready, and you’re not, that’s all I’m saying.” Sally retorts: “And in the meantime, you’re going to ruin your whole life waiting for it.”

It’s an astute observation, one that shrewdly reveals Harry’s greatest flaw. Pessimistically believing everything will turn out poorly, his mentality infects his relationships with others. “Eventually, things move on, and you don’t take someone to the airport, and I never wanted anyone to say to me ‘How come you never take me to the airport anymore?'” His avoidant personality belies a genuine horror of being emotionally vulnerable, resulting in commitment issues. He’ll sleep with practically anyone, but he’ll always keep an eye on the door, a single foot placed outside the bed to ensure a speedy exit.

On the other hand, Sally is an incorrigible perfectionist—“I just want it the way I want it.” She dates much the same way she orders at a restaurant, only going to bed with someone when it feels right, throwing Harry’s libertine behaviour into sharp relief. However, she bemoans the fact she’s too structured, with a similar inability to admit to what she wants, delaying her romance with Harry in the process.

There’s no real plot. There’s no prominent situation. The entire story revolves around when Harry met Sally—on three separate occasions in their lives—and how their neurotic foibles kept them apart. That their interactions reveal character organically is perhaps the greatest strength of Ephron’s script; it’s a film of conversations, an honest depiction of those moments in life where two people genuinely connect. As such, When Harry Met Sally… becomes a moving film about human relationships.

But how exactly do they connect? The film’s central thesis—one proffered by Harry, who believes himself to be an expert in the psychosexual nuances of the human condition—suggests that men and women can never truly be friends. “The sex part always gets in the way,” Harry declares, educating Sally on their drive to New York with the smug arrogance of a pedagogue. The production even used a whimsical variant of this axiom as the tagline to promote the film: ‘Can two friends sleep together and still love each other in the morning?’

A preposterous claim, but one born out of Harry’s cynical nature. When he elaborates on his hypothesis, he makes it abundantly clear that it’s down to human failings that such friendships can never work. Much like he fears his wife chastising him for not taking her to the airport, he thinks through endless permutations, always deciding the worst one is the most likely. His desire to avoid conflict causes him to become isolated.

It’s such a preoccupation with male-female relationships that places dating conventions at the forefront of the film. Harry’s description of life as a single bloke, Marie’s (Carrie Fisher) Rolodex collection of potential lovers, and endless discussions about what being in a relationship means. What’s the significance of a married man spending $1,600 on a dining room table? Or your girlfriend suspiciously never wearing Sunday from her days-of-the-week underwear collection? All the answers can be found in Ephron’s script.

Of course, the rules of engagement differ for men and women, something Harry expatiates on endlessly. He describes women in clingy, emotional terms, framing it as a nuisance, if not a total character flaw. “How long do you like to be held after sex? All night, right? See, that’s your problem. Somewhere between 30 seconds and all night is your problem.” Not only is he in complete denial about his emotional inabilities, but he also adroitly repositions his shortcomings as insecurities of the female sex, eschewing the need for self-reflection.

In discussions about dating etiquette and the differences between the sexes, sex becomes a rather explicit topic in When Harry Met Sally… Most of cinema’s best rom-coms were made before the Hays Code’s dissolution, meaning carnal acts and physical intimacy were rarely discussed so openly. Rob Reiner’s classic film makes deliberate reference to the sexual mores that pervade male-female dynamics.

This also leads to what is undeniably the most iconic scene from the film: Sally’s faked orgasm sequence in the restaurant. “I’ll have what she’s having,” says an intrigued customer, who just happened to be played by the director’s mother. But perhaps the even more amusing sequences come from the less Hollywood-esque scenes. Particularly, Harry and Sally divulging their various sexual dreams is hilarious, whereas Jess’s (Bruno Kirby) astonishment at another man’s prowess in the bedroom is deeply funny: “You made a woman meow?”

Just like the film’s tagline suggests, the story isn’t just about sex, but about friendship too. Friedrich Nietzsche once wrote: “It is not a lack of love, but a lack of friendship that makes unhappy marriages.” While the German philosopher may never have married himself, it remains a shrewd observation, one that reveals Harry’s central challenge: overcoming the dichotomous nature of his initial hypothesis. 

He bolts out the door after sleeping with Sally because he fears it has ruined their friendship, instead of strengthening it. In his mind, they are friends, not partners, with the two concepts being mutually exclusive. However, overcoming this deep-rooted neurosis isn’t easy for Harry, and it threatens to destroy his relationship with Sally. His avoidant personality leads him to run away at the first sign of trouble. When Sally refuses to chase him, it becomes clear that it’s up to him to make the necessary changes if they are ever to be together.

Surprisingly, When Harry Met Sally… thus becomes a moving meditation on urban isolation. Reiner seems to suggest that such malaise is conquered by love and friendship, but when Harry rids himself of either, he realises just how destitute he truly is. His meandering through the desolate city streets on New Year’s Eve is a moment of poignant sincerity in the film: the life of a single man is shown to be a truly miserable existence, wordlessly conveying that sex without love is a barren, nihilistic affair.

Then, he runs. Realising his terrible mistake, Harry sprints headlong back to the one he loves. Mirroring the ending of The Apartment (1960), it’s a moment that never fails to stir emotions. Understanding that the only way to cast off the yoke of oppressive loneliness is to forge deep, meaningful relationships, he races to find Sally before midnight. While the following monologue is what people remember most, I cherish his unadorned declaration of love: “I’ve been doing a lot of thinking, and the thing is, I love you.” Much like the film itself, it’s simple, pure, and genuinely heartfelt.

Choosing the best film in any genre is difficult, with the rom-com being a particularly crowded category. As previously mentioned, many of the greatest rom-coms were made during Hollywood’s Golden Age. Bringing Up Baby (1938) is another personal favourite, with the wacky screwball comedy remaining hilarious even on repeat viewings. George Cukor’s efforts in the genre, including The Philadelphia Story (1940)—Hepburn and Grant at it again—and Adam’s Rib (1949), are also top contenders.

Other auteurs with a keen aptitude for the genre include Billy Wilder and Woody Allen, both of whom could claim to have directed the best rom-coms ever produced. Wilder’s Some Like It Hot (1959) is perfect, although it sacrifices some focus on romance in its bid to become the funniest film ever made. The Apartment, as mentioned, is a more balanced rom-com, and a superlative one at that. Meanwhile, Allen’s Annie Hall (1977) and Manhattan (1979) are both as funny as they are moving, demonstrating the auteur’s natural talent for weaving love and romance into the intricate tapestry of life.

However, I would still argue that When Harry Met Sally… is the greatest rom-com ever made. Perhaps it’s the mesmerising simplicity of Reiner’s film: the movie predominantly only features two people in a shot, talking about their lives and the issues currently plaguing them. The editing and pacing are stunning, effortlessly conveying how two people fell right into each other’s arms (though it took a few tries). Montage is used expertly to show two lonely souls getting to know each other through their idiosyncratic daily interactions; occasionally frustrating, but ultimately cherished, especially when lost.

Is it mere chance that Harry and Sally should continue to meet after years of separation, or that they should bump into each other just as the clock strikes midnight? The random forces of the cosmos, or the hand of fate? Our film is intermittently broken up by couples discussing the serendipitous nature of their love, and the unlikely stories behind their pairings.

This is truly what When Harry Met Sally… is about: how people meet and how they fall in love. It’s about dating, sex, despair, and loneliness, encompassing much of what makes romance fragile, precious, and sometimes, very difficult. But most importantly, the beauty of Reiner’s film can be found in how our protagonist subtly informs us what love, life, and the story itself, are truly all about: “It’s about old friends.”

USA | 1989 | 95 MINUTES | 1.85:1 | COLOUR | ENGLISH

Cast & Crew

director: Rob Reiner.
writer: Nora Ephron.
starring: Billy Crystal, Meg Ryan, Carrie Fisher, Bruno Kirby, Steven Ford, Lisa Jane Persky, Michelle Nicastro, Kevin Rooney & Harley Kozak.