The questions "When Harry Met Sally" make us consider today

Maybe we’ve been looking for the wrong answers from “When Harry Met Sally.”  Easy enough to do, since the plot revolves around the question of whether men and women can truly be friends.

Billy Crystal’s Harry Burns is very sure he knows the right answer at the tender age of 21 when, during their 18-hour road trip to New York, he tells fellow University of Chicago graduate Sally Albright (Meg Ryan) that such relationships are impossible “because the sex part always gets in the way.”

Nora Ephron’s script doesn’t present a thesis that hadn’t played out in any number of romantic movies before Rob Reiner made it into a standard-bearer for romantic comedies. She simply chose not to disguise her dance of witty banter in “will they/won’t they” lingerie. Even the trailer skips right over that – they absolutely do.

This being a romance, the audience is left with the best version of that interlude’s outcome since they break up, only make up and kiss again thanks to Harry’s legendary New Year’s Eve speech and the denouement.

“Happily ever after” is a foregone conclusion in rom-coms, and has been since this film became an instant classic. Wrapping their tale that way may have satisfied the audience, but it also left that headlining question unanswered. Yes, they became friends. Then they got married, so . . . ?

Nearly three and a half decades after “When Harry Met Sally” became an instant classic it’s either a settled argument, since so many people have platonic friendships with members of the opposite sex, or impossible to agree on.

It’s also understood to be an unrealistic depiction of romance. This doesn’t refer to the part about men and women being friends, but the idea of any pair of relative strangers organically getting to know each other at all.

This occurred to me during my latest rewatch, this time from the perspective of a middle-aged woman whose two best friends are single and constantly sharing their horror stories.

Dating apps and social media have gamified the promise of human connection. Even the ones that are supposedly dedicated to helping women sort relationship material from the first-generation Harry Burnses, the ones who wonder out loud how long a man is obligated to hold a woman after sex, are easily circumvented by said monsters.

On the other hand, we keep hearing stories about male loneliness – how men are less likely than ever to have friends and how difficult it is for anybody at any age to find connection with other human beings.

Much of this coverage looks at middle-aged men but other polls suggest this epidemic is hitting younger ones too. One 2024 report from the Survey Center on American Life found that only 56% of Gen Z adults and 54% of Gen Z men were involved in a romantic relationship when they were teenagers. Approximately 44% of Gen Z men report having no relationship experience at all during their teen years.

This echoes the findings of a 2018 study by the Cigna Group and market research firm Ipsos, in which Gen Z and Millennial adults reported themselves to be lonelier than older respondents.

But there’s also hard data to show that Sally’s fear of being 40 and single (“Someday!”) would make her less of an outlier today since, as of 2021 analysis of Census Bureau data by Pew Research Center, a quarter of American adults report never having been married.

Maybe the evergreen draw of “When Harry Met Sally” isn’t in the overt romance that grows between them but in the series of interactions where they get to know each other. That includes the conversations they share with their friends  – Sally with her best friend Marie (Carrie Fisher), and Harry with Jess (Bruno Kirby), his buddy who, like him, thinks he has everything figured out.

We can’t count out its setting, centering a version of New York that is timeless and probably doesn’t exist anymore. The city is a connector where small apartments push residents to make public places their living rooms. Running into like-minded people is common. Therefore, Harry and Sally’s chance meeting in a bookstore more than a decade after their disastrous car trip is organic. She’s freshly broken up with her boyfriend Joe, and his wife has just left him.

(Everybody has their favorite lines from this movie; one of mine is Ephron’s sly way of acknowledging Harry’s newfound vulnerability when Marie murmurs to Sally, upon noticing Harry spying on them, “Someone is staring at you in ‘Personal Growth.’” )

From there Marie makes her exit so Harry and Sally can grab a meal, go for a walk and deftly reset their familiarity.

Harry and Sally are a pair of lonely people who got their hearts broken by people they fell in love with before they really got to know them. Audio of a depicted phone call they share while watching “Casablanca” together plays over scenes of each of them miserably enduring their solitude or trying to ignore it before deciding to be lonely together.

As their platonic connection develops, they call each other on their lack of consideration and learn to endure the other one’s quirks better than anyone else.

Watching old movies over the phone – a landline, no less! – could still happen. Nowadays that shared experience likely would be facilitated by a video call and screen sharing.

Technology and landscapes change, and technology changes landscapes: in 2024 bookstores are as rare as chance meetings. Tech has also been blamed for the withering of some of the basics of our social contract, namely the ability to be honest and open with other people, which forms the basis of Harry and Sally’s relationship.

The Cigna study also found that social media use was not solely to blame; a disconnection from family and social connections was also a major predictor.

It also preceded the pandemic, which only served to make people feel even more distant than they did before. Constantly updating data from a YouGov tracker poll confirms that, with 21% of adult respondents on July 3, 2024, answering the question “Thinking about the past week, on how many days have you set aside a minimum of an hour specifically for socializing with other people?” with “None.”

Coming in second place is “Every day” at 19.6%, so there’s that.

Chance meetings between people still happen all the time. I swear, they do! But back then they looked so easy. In early June a column in The Cut titled “Is Dating a Total Nightmare for You Right Now?” went viral, connecting a string of social media posts featuring women sharing their dating horror stories. Its lead subject is Anya Haas who posted a painfully honest TikTok in mid-May detailing her frustrating experience of a night out in Austin.

“I’ve been trying to meet someone, just anybody worth my time for years,” she said. Dating apps are awful, the 33-year-old says, so she’s been trying to meet people in public. It did not go well, especially when she went to a local comedy club and sat in the front row where the comics kept calling out the fact that she was alone. “I’m tired of it. I’m over it. I’m sick of it. When I try, like, s**t like this happens.”

In the main Haas was lamenting how impossible it’s been for her to meet a guy after seven years of being single. But the part that stuck with me is that the app that instigated her evening from hell was designed to facilitate meeting people. That’s all she wanted, to at least “meet people that I can become friends with.” That’s not too much to ask, right?

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If only Ephron were around to answer that question; she died in 2012. A year after the movie came out, though, the script was released in book form with a foreword Ephron wrote to clarify her position on that question.

“The truth is that men don’t want to be friends with women. Men know they don’t understand women, and they don’t much care,” she writes. “They want women as lovers, as wives, as mothers, but they’re really not interested in them as friends. They have friends. Men are their friends. And they talk to their male friends about sports, and I have no idea what else.

“Women, on the other hand, are dying to be friends with men,” Ephron continued. “Women know they don’t understand men, and it bothers them: they think that if only they could be friends with them, they would understand them and, what’s more (and this is their gravest mistake), it would help. Women think if they could just understand men, they could do something. Women are always trying to do something.”

Are they though? Nowadays their fatigue with so much doing has led to many women — and men — trading disappointment and frustration for removing themselves from the dating merry-go-round.

Cinematic romances are so much easier to navigate and readily available thanks to streaming. We know how those end.

Still, for all of the bittersweet fantasy that “When Harry Met Sally” peddles, there is realism in the way Ephron’s writing and Reiner’s direction trace the contours of intimacy between two people, slowly built over months and time spent together.

So the question one might ask may be related to that. What have we lost over the last 35 years that makes this friendship/love story almost mythical in its ability to affect us? Answering that won’t necessarily solve the mystery driving the soundtrack composer Harry Connick Jr.’s lyric about making lovers out of friends. But it could reduce the number of strangers in our lives, which may be a start.