Year: 1989
Director: Rob Reiner
Writer: Nora Ephron
Starring: Billy Crystal, Meg Ryan


Easily the most accessible film in Sexcatraz, When Harry Met Sally was a runaway critical and commercial success, grossing US$92 million in the US alone and earning a Best Screenplay Oscar nomination for Nora Ephron. Although the inspired pairing of Billy Crystal and Meg Ryan significantly contributes to the film’s success, the springboard is Ephron’s savagely accurate vivisection of society’s unconscious, shame-based sexual covenants.

The film covers a 12-year period from when Harry Burns (Crystal) and Sally Albright (Ryan) first meet to when they actually become a couple. Spanning long time periods can be problematic in cinema, but When Harry Met Sally neatly solves this by interpolating each sequence with a brief interview with a married couple recounting how they first met; this artificial device—referenced by the film’s title—is cleverly stitched into the main thread by making Harry and Sally the final interviewees.

The main plot gets underway when Harry, fresh out of college, hitches a ride from Chicago to New York with Sally, a friend of Harry’s then current girlfriend. Harry and Sally are an oil-and-water combination; he’s crude, cynical and opinionated while she’s demure, optimistic but high maintenance. Tempers flare during the long drive but Harry finds Sally increasingly attractive and playfully hits on her. Sally deflects his advances by averring they are “just going to be friends.” The film’s first telling moment comes when Harry rebuts this: “Men and women can’t be friends because the sex part always gets in the way.” Harry’s—and Ephron’s—logic is impeccable but it’s not until later that Ephron, through Harry, fully deconstructs this statement.

When Harry Met Sally

Skip five years and Harry bumps into Sally on a plane. She has a new man; Harry is engaged but hasn’t lost any of his cynicism, as his description of the singles scene reveals: “Go back to her place, you have sex, and the minute you’re finished, you know what goes through your mind? How long do I have to lie here and hold her before I can get up and go home—is 30 seconds enough?” The drivers for both responses—her desire to be held and his to elope—are our sexual covenants and their underlying shame. Having satisfied his sexual impulse, he suddenly feels ashamed of his predatory actions. Frank Booth in Blue Velvet, Bud in The Brown Bunny, and Jay fleeing from Pam in Intimacy all demonstrate this post-orgasmic polarity switch. The sense of having transgressed (sex without love) impels the man’s flight to lessen his unpleasant feelings of guilt and shame. Conversely, the woman feels that the man’s continued presence adds legitimacy to the sexual transaction, in the same way that Elena goes through emotional somersaults in À Ma Soeur! to convince herself that Fernando genuinely loves her.

What is also noteworthy here is how gender traits influence responses to shame. This is a broad generalisation, but men typically respond to awkward situations through action while women respond through emotion. These contrasting traits underlie the contentious question, “Will you still love me in the morning?” If he sticks around after sex for breakfast… then lunch… then dinner… then it must be love. (Actually, he’s just hungry.) Truly experiencing the array of unpleasant feelings generated by sexual shame and guilt is the last thing most people want, so he’s off to the pub to catch the early kick-off, leaving her feeling emotionally violated—as Elena felt in À Ma Soeur! and Sally will later feel in When Harry Met Sally.

On the escalator after the flight Harry fleshes out his earlier ‘men and women can’t be friends’ dictum: the only reason people in a relationship look for friendship with the other sex is because they are sexually dissatisfied; in order to disprove this (and prove their fidelity to their partner, with whom they have exchanged sexual access rights) they avoid making friends with the opposite sex

On the escalator after the flight Harry fleshes out his earlier ‘men and women can’t be friends’ dictum: the only reason people in a relationship look for friendship with the other sex is because they are sexually dissatisfied; in order to disprove this (and prove their fidelity to their partner, with whom they have exchanged sexual access rights) they avoid making friends with the opposite sex. When Harry Met Sally is peppered with such revealing exchanges. Screenwriter Nora Ephron’s faultless logic compels Sally to prove that she has no sexual interest in Harry and she rejects his offer of friendship.

Jump another five years and Sally is recently single while Harry is getting divorced. The collision takes place in a bookstore and this time leads to dinner, over the course of which Ephron unearths another cost of our sexual covenants. This time Sally is the mouthpiece: she and her previous partner didn’t marry because almost all the married couples they knew “practically never had sex again. It’s true—it’s one of the secrets that no one ever tells you.” (Despite revealing this unspoken truth the film ultimately marries off its protagonists, upholding the conventional view, already seen in Eyes Wide Shut, Unfaithful and Indecent Proposal, that romantic love means everything and sex nothing.)

When Harry Met Sally

The upshot of the dinner is a platonic friendship between Harry and Sally and the film’s most assured sequence, gorgeously framed by an autumnal New York. Both of them date other people but there’s a crucial difference: Sally doesn’t have sex with these try-before-you-buy partners while Harry does. Sally’s distaste for Harry’s behaviour spirals into the film’s best-known scene, where she fakes an orgasm in a diner to prove a point. It’s a funny moment but it’s worth deconstructing the underlying psychology. If a woman is genuinely enjoying sex she has no reason to fake an orgasm. Her joy will be transmitted to her partner, regardless of whether she climaxes. An orgasm is only faked to short-circuit an emotionally unrewarding sex act, making the man feel cock-a-hoop about his sexual prowess as—obeying Harry’s earlier 30-second rule—he scurries out the door feeling he can get away with a quick exit. All of the damaging behaviour so humorously documented by Nora Ephron in When Harry Met Sally is founded on shame.

As it moves into its second half When Harry Met Sally affords progressively more screen time to its protagonists’ best friends, Jess (Bruno Kirby) and Marie (Carrie Fisher), with a corresponding fall-off in its charm. The inevitable upshot is a double date where Harry pairs with Marie, and Jess with Sally. Equally inevitably, Jess and Marie instantly fall for each other. The progression of their relationship through engagement to marriage forms the external spine of the final third of the film.

But the idyll between Harry and Sally cannot last as they are both increasingly affected by their shame-based, emotionally disempowering beliefs. Hitting a low, Harry and Sally turn to each other for support and end up having sex. Harry immediately knows the score: they have violated his own dictum and their friendship is accordingly doomed. Here the film makes its only emotional misstep; the usual response to shame-induced feelings of awkwardness, foolishness and humiliation is avoidance. Instead, they meet for dinner the following night in an attempt to paper over their awkward feelings by dismissing the sex as a mistake.

When Harry Met Sally

It doesn’t work. By the time of Jess and Marie’s wedding, Harry and Sally have drifted apart, blaming each other for the demise of their friendship. This sparks an argument that reveals just how important the emotional legitimacy of our sexual liaisons is, particularly to women. Sally: “You want to act like what happened didn’t mean anything.” Harry: “I’m not saying it didn’t mean anything; I’m saying why does it have to mean everything?” Sally: “Because it does!” Sally’s heated response stems from the unconscious pressure to frame sex within love already explored in detail in Intimacy. Our covenants prevent many people from enjoying sex purely for its own sake, as Harry and Sally now find to their cost.

But this is a Hollywood romantic comedy and we know how it’s going to end. Harry and Sally realise they’ve been in love all along and therefore their lovemaking, like that between Diana Murphy and John Gage in Indecent Proposal and Jay and Claire in Intimacy, was emotionally legitimate after all. The audience gets the ‘up’ ending it craves but the downside—the difficulty of cross-gender friendships and the inadmissibility of sex between friends—remains unresolved.

Without showing an inch of skin When Harry Met Sally is among the most revealing films ever made about society’s sexual covenants. Nonetheless, it follows Eyes Wide Shut, Unfaithful, Indecent Proposal and Intimacy in ultimately upholding those covenants; its commercial success depends on this, as its target audience largely adheres to the belief that sex is only meaningful within the envelope of love. A film that explores the collision of love and sex—and dares to reject the conventional viewpoint—is Catherine Breillat’s anti-heroine sex odyssey Romance.


Start: Sexcatraz Pt. 1 – Welcome to Sexcatraz
Previous: Sexcatraz Pt. 29 – Intimacy
Next: Sexcatraz Pt. 31 – Romance


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