When Harry Met Sally

He's All That (Oops! All Romcoms: Part 4 of 4)

Meg Ryan and Billy Crystal

I saw it first as a 10-year-old kid and didn’t get it. People talk a lot, and nothing happens. I also didn’t recognize Princess Leia without the bikini. The faked orgasm at the deli was funny to my grade-school sensibilities, though. 

When I was older, somehow, we incorporated the famous deli orgasm scene into a wildly inappropriate skit during a Korean church youth group retreat. WWJD? Probably not that. (Another time, we did a Baby Got Back skit at a youth group summer camp that involved numerous gyrating/twerking Christians in tight dresses, but it was ok because we did it for the glory of God. Now that Korean church youth groups are mainstream, thanks to Steven Yeun and Beef, I can finally reference these things.) I understood the movie to be asking if men and women could be friends, which is a stupid question because of course they can. This is like asking if Mifepristone is safe when it’s been used in the US for 20+ years and a decade before that in Europe without issue. 

I didn’t see the movie again for decades after that. When I recently rewatched it as a middle-aged man, I realized When Harry Met Sally is asking an entirely different question, one I didn’t notice as a kid and later as a horny-yet-Jesus-loving teen. The movie asks what is essentially a biblical question: Can an awful man change? Can he be redeemed? The answer is yes, but with caveats that steer the movie away from the simple redemption tropes common to rom-coms. It takes time (12 years!); searing, emotional pain; and a woman savior. 

We don’t see this squarely since it’s played for laughs, but Harry is a toxic piece of shit. During the long drive from Chicago to New York City, he dismisses Sally’s professional goal of being a reporter. (“So you can write about things that happen to other people?”) He makes crude, insulting assumptions about her personal life. (“Obviously, you haven’t had great sex yet.”) He also propositions her despite having a girlfriend to whom he had sloppily professed his undying love earlier that day. And he’s spitting out grape seeds from the car. The spitting is coarse, but who eats seeded grapes? Only a real piece of shit. 

They meet again five years later, and he’s gotten worse. At first, he doesn’t remember Sally and asks if they ever had sex, as if it would be forgettable for him but an unforgettable event for her. Harry follows up by asking if her friendship with his girlfriend at the time was worth the sacrifice of not having sex with him! This is Andrew-Tate-level arrogance and misogyny.

Why is Harry such a repulsive, egotistical man? Maybe for the same reasons I didn’t recognize the depths of his shittiness in numerous past viewings. He’s funny and disguises the crude, careless way he treats others with humor, which allows him to get away with being terrible. Further, judging by the size and quality of his New York City apartment, he’s making a lot of money, and if he’s not exaggerating, he’s having a lot of sex. What incentive does a man have to change if the universe is showering him with rewards, both monetary and sexual? This question is addressed in the next phase of the movie.

Another five years pass, and they meet again. Sally spots Harry lurking in the personal growth section of a bookstore. He’s miserable and has been working on himself. The pain of divorce has humbled him and kickstarted a metamorphosis. He’s reforged his personality, no longer speaking to others like an unrepentant shock jock. This time, he sympathetically listens to Sally talk about the dissolution of her five-year relationship with Joe and speaks honestly about his failed marriage. However, his come-to-Jesus moment has not quite arrived. Near the end of their pleasant day together, he insults her, momentarily reverting to his old ways. 

Harry: You know, the first time we met, I didn’t really like you that much. 

Sally: I didn’t like you.

Harry: Yeah, you did. You were just so uptight then. You’re much softer now.

Sally: You know, I hate that kind of remark. It sounds like a compliment, but really, it’s an insult. … I just didn’t want to sleep with you, and you had to write it off as a character flaw instead of dealing with the possibility it might have something to do with you.

Sally calls him out, giving it back just as hard as he dished it out. Harry apologizes wholeheartedly and charmingly. (“What’s the statute of limitations for an apology?”) Sally makes him recognize and correct his poor behavior like one of those amazing dog trainers on TV. She has the near-superhuman ability to rebuke someone immediately, accurately, and viciously. She does this throughout the rest of the movie when Harry relapses into an asshole. My favorite rebuke comes after Harry says there’s something wrong with Sally because she hasn’t slept with anyone since breaking up with Joe. She responds: 

That will prove I’m over Joe? Because I fuck somebody? Harry, you’re gonna have to move back to New Jersey because you’ve slept with everybody in New York, and I don’t see that turning Helen into a faint memory for you. 

Sally shoves Harry’s words back at him, forcing him to acknowledge the nonsense logic at the heart of the insult and his pathetic attempts to use sex to get over his ex-wife. After she makes it crystal clear he is exhibiting awful behavior, he again apologizes immediately. With her words, she is exorcising the caustic demons within Harry.

Sally is the white knight in this story, saving Harry from self-inflicted misery and loneliness, from the fate he had predicted for her during their first meeting. (“...suppose you die one of those New York deaths where no one notices for two weeks until the smell drifts into the hall?”) When Harry Met Sally is also a man’s fantasy. A man can act however he wishes, spewing hateful comments; sleeping with a legion of women with the appetite one brings to an all-you-can-eat buffet; only grudgingly evolving into something more than a troglodyte. Because, in the end, a bright, beautiful woman will still be there and ready to love him if he says the right words. I love this movie because the brilliant writer, Nora Ephron, knows the right words. She believes words have magical properties. To her, words--and not something as superficial as physical attraction--spark love, but more than that, words perform alchemy. They transform hate into love and a vile piece of shit into someone worth spending your life with. 

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When Harry Met Sally
Written by Nora Ephron; Directed by Rob Reiner
1989
95 minutes
English