The High-Maintenance Problem with The Atlantic’s Revisiting "When Harry Met Sally"

The High-Maintenance Problem with The Atlantic’s Revisiting "When Harry Met Sally"

By David Himmel

If I had to choose my top five favorite romantic comedies without spending too much time thinking about them, they would be:
1. Annie Hall
2. Grosse Point Blank
3. When Harry Met Sally
4. High Fidelity
5. Better Off Dead

Now, having done that, I realize that I might have a thing for John Cusack. But this isn’t about that. This is about When Harry Met Sally, which was released on July 21, 1989. Being that it’s thirty years old, retrospectives of this adored movie were bound to come out. On July 19, The Atlantic published “The Quiet Cruelty of When Harry Met Sally” by Megan Garber. The subhead reads: “The classic rom-com invented the ‘high-maintenance’ woman. Thirty years later, its reductive diagnosis lives on.”

When Harry Met Sally struck a chord with us then and its affects linger with us now, which Garber did a wonderful job of pointing out in her piece. It is a well-written piece, structurally. But her thematic positioning is off the mark.

Her issue, made clear in the subhead, takes issue with the scene where Harry (Billy Crystal) tells Sally (Meg Ryan) that she is a high-maintenance women. The worst kind, at that. “You’re high-maintenance, but you think you’re low-maintenance,” he tells her.

Garber writes, “[T]he term today does precisely what it did 30 years ago, as backlash brewed against the women’s movement: It serves as an indictment of women who want. It neatly captures the absurdity of a culture that in one breath demands women do everything they can to ‘maintain’ themselves and, in the next, mocks them for making the effort. She wears makeup? High-maintenance. She shops? High-maintenance. She’d prefer the turkey burger? High-maintenance.”

But Harry doesn’t list Sally’s fashion sense or desire to shop or what item on the menu she wants as examples of her high-maintenance behavior. He uses one example of how she is particular with how she wants the item on the menu she’s chosen. Garber quickly over generalizes and assumes intention. She’s not alone. It’s what many have done with the phrase over the last thirty years.

Garber points the blame at Harry when she writes, “It’s so casual. It’s so bluntly efficient. The man, inventing the categories, and the woman, slotted into them. The man exempt; the woman, implicated.”


There’s a difference between being high-maintenance and being difficult. Sally is quite likable. Which is exactly why Harry befriends and falls in love with her.


To give credit to Harry’s glib assessment of Sally as “the worst kind” of high-maintenance creating yet another negative box with which to put women as feminist backlash at the hands of a male director and character is to give it too much credit. If we’re going to talk about Hollywood productions creating tiny boxes for women to exist, we must look directly at Sex and the City. The TV show, the films, as well as the source material and the author of the book and so many of the others penned by Candace Bushnell.

The four women weren’t shallow characters, but we the viewers did everything we could to drain the little depth they did have by posing and answering the question of Which Sex and the City Character Are You? (I’m such a Miranda, by the way.) It’s a terrible thing we do to women, but it’s not just female characters who are boxed in. The men of Sex and the City were stereotyped and shoved into shoddy bivouacs of categorization. Mr. Big, the rich dreamboat; Aidan Shaw, the nice guy who finished last; Jack Berger, the tortured, self-loathing writer; Aleksandr Petrovsky, the aloof foreigner who rejects American customs; Harry Goldenblatt, the safe Jewish lawyer who was too bald for Charlotte to even consider dating at first; Smith Jerrod, the young hunk who was perfect until he no longer needed Samantha to reaffirm his value. As a man living a single life hunting for companionship during the height of Sex and the City’s influence, I had to wade through these male stereotypes constantly. It sucked.

And I’m sure the same kind of wading sucks for women.

Simple, stupid character categories and stereotypes exist all over the place in popular media. How we invite them into our real lives and use them to govern our opinions and decisions is not the responsibility of the writer, actor, or director. It’s ours.

Garber writes, “But high-maintenance is one of a particular subgroup of pop-cultured insults that are applied, most commonly, to women — a category that whiffs of feminist backlash. There’s MILF, popularized by American Pie; and cougar, popularized by the 2001 book Cougar: A Guide for Older Women Dating Younger Men; and cool girl, introduced by Gone Girl; and gold digger, an insult of long standing recently revived by Kanye West. There’s butterface, derived over time from movies and music. There’s Monet (Cher in Clueless: ‘From far away it’s okay, but up close it’s a big ol’ mess’). There’s cankle — whose coinage added one more entry to the ever-expanding list of body parts women might feel insecure about — popularized by the allegedly romantic comedy Shallow Hal. (‘She’s got no ankles,’ Jason Alexander’s character, Mauricio, says. ‘It’s like the calf merged with the foot — cut out the middleman.’)”

Some of these are insults. Cankle is mean. Butterface isn’t all that nice. But calling someone a Monet is less an insult and more a dig at the unfortunate reality that some of us look better from far away thanks, in some part, to makeup. And yes, women and makeup is an issue steeped in sexism. But I could be a Monet, too. Maybe I am. Beauty and taste are in the eyes of the beholder.

My wife and I had a conversation early on in our dating days about women shaving their legs. She was all for letting her hair grow. I said that I had no problem with women who don’t shave their legs or their arm pits or whatever else. But I’m not sexually attracted to hairy legs. That’s just my preference. There are plenty out there who may find someone I consider a Monet to be the most gorgeous face on this planet. And that’s great. That’s how it should be. Different strokes and all that.

High-maintenance doesn’t have to be a bad thing. Owning a boat requires high-maintenance and I love owning a boat. Being a parent to a toddler requires high-maintenance and I love being a parent to a toddler. Flying a plane, driving a race car, being a professional athlete at the top of your game… all things that are high-maintenance. There are those who don’t want to deal with that sort of stuff, and that’s perfectly okay. Driving a Honda Civic to brunch with your friends while wearing a baseball hat because you didn’t style your hair is pretty low-maintenance. And there’s nothing wrong with that.

As it relates to Sally being high-maintenance, Garber misses the fact that there’s a difference between being high-maintenance and being difficult. Harry, while he does pin the term on Sally as a mark in the negative column, does not say she’s difficult. Because she’s not. She just wants it the way she wants it. She’s never rude to anyone when ordering a meal or whenever she’s being high-maintenance. And because of that, she’s not difficult or mean or snooty. Sally, for the most part, is quite likable. Which is exactly why Harry befriends and falls in love with her.

In the climax of the film, after Harry has stormed into the New Year’s Eve party and confronts Sally, he lists all of the high-maintenance things about her as top reasons he loves her so deeply. If that’s so, how can it be a negative thing? For all that I love about my wife and friends and family, I would never list the things I dislike about them as reasons I love them. Or would I? Perhaps that’s what makes human relationships so complicated. We love or hate the whole package. For good or ill. 

Harry is a jerk. Well, it’s his veneer. Harry is a typical male who flairs his feathers and pounds his chest to present himself as an alpha male. When we meet him, his a smug college graduate — a kid. He’s sure of himself and his view of the world and no one can shake his confidence. Because he’s a twenty-something in his sexual prime, he’s going to over simplify the complexity of relationships because that’s what twenty-somethings do when they’re trying to get laid, which is what Harry is trying to do.

Later, after he’s been married and divorced, he’s a broken man. Even after he comes out of his mopey funk, he maintains his guard because he’s been hurt, hurt bad, and doesn’t ever want to feel that pain again. This is the Harry we have when he makes the high-maintenance accusation. Who among us hasn’t been cold and closed off and dumbed down human personality traits to the most simple state when trying to protect our wounded heart and ego? If you answered, “Me! I’ve never done that!” then you’re a liar or have never been hurt bad enough or are too careless with your feelings. But there I go… over-simplifying things and putting in a box.


When Harry Met Sally removed the honesty, the reality to make room for laughs.


Harry is only likeable because of his wit. He grows on us and we forgive his stupid comments because that’s what we do with people. When the good we see in people outweighs the dumb shit that comes out of their mouths, we forgive that dumb shit. We laugh at it. We find it charming. And thank Christ we do otherwise I wouldn’t have a single friend to my name.

But do not mistake that last statement as a defense of Harry. That conversation he and Sally have in their respective beds via split-screen is Harry at his most obnoxious in effort to deflect Sally from noticing his vulnerability. At that point in the film, he may well already be in love with her. Even so, I’m not defending Harry because there’s nothing to defend. It’s a pithy conversation between two friends. Yeah, it occurred in one of cinema’s most beloved films but so what? To take anything anyone says late at night during drowsy conversation over the phone as Rule is silly. Not every line of dialogue should carry equal amounts of weight.  

Garber writes at the end of her article, “Movies’ magic can take many forms. Their words can become part of you, as can their flaws. Thirty years after When Harry Met Sally premiered, in this moment that is reassessing what it means for women to desire, it’s hard not to see a little bit of tragedy woven into comedy’s easy comforts.”

She’s spot on there. Tragedy and comedy go hand-in-hand in theatre, be it on the stage or the screen. According to the short documentary How Harry Met Sally, director Rob Reiner and writer Nora Ephron both planned on ending the film with Harry and Sally not pursuing a lasting romantic relationship, choosing to remain friends instead. But they caved to the Hollywood ending because, well, Hollywood. Though they both agreed that ending was far from realistic.

The impetus of the When Harry Met Sally story was based in reality. Reiner wanted to make a film where two people became friends but didn’t screw because it would ruin the friendship. Ephron liked it and signed on. She based the Harry character on Reiner’s experience as a man reentering the dating life following his divorce from Penny Marshall. Crystal, Reiner’s best friend at the time, punched up the screenplay to make Harry funnier. Because before Crystal got hold of him, Harry was an even greater misanthrope. Ephron based Sally’s character on her friends.

Reality, as representative as it is in art today and thirty (forty, fifty, sixty…) years ago, is not what movies are. And certainly not romantic comedies. Annie Hall may be the truest of all romantic comedies. But Annie Hall wasn’t meant to be a romantic comedy. It was originally intended to be a look at the man in a mid-life crisis. The end result is essentially one chapter of that larger idea. Allen even sacrificed some laughs in order to tell a story about human beings, according to a PBS documentary about the writer-director.

When Harry Met Sally is the opposite. It removed the honesty, the reality to make room for laughs. So to take anything from a movie that was positioned to pull laughs from a culture using characters that had been twisted out of real people and real feelings is both oversimplifying and over aggrandizing the point of a romantic comedy. It’s lazy thinking, really. And lazy thinking is the kind of thinking done by low-maintenance kind of people.

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