A Look Back at ‘You’ve Got Mail’ – the OG Online Dating Rom-Com

You’ve Got Mail is considered an archetypal romantic comedy, but at its heart is a film about anxieties surrounding the Internet, and the ways it impacts our lives and relationships, even before we were all Tindering our lives away. Lizzi Sandell revisits You’ve Got Mail for the film’s 20th b-day.

In December 1998, when “online” was still two separate words, Nora Ephron made a movie about two New Yorkers who find unlikely love through an email exchange. You’ve Got Mail stars two of Ephron’s muses, Meg Ryan and Tom Hanks, who had already appeared opposite one another five years earlier in Ephron’s directorial breakthrough, Sleepless in Seattle. Ryan plays whimsical wet blanket Kathleen Kelly whose late mother’s children’s bookstore The Shop Around The Corner is her pride and joy. Hanks plays Joe Fox, whose family corporation, Fox Books, is taking over Manhattan one Barnes-and-Noble-esque superstore at a time. They meet anonymously online, Joe puts Kathleen out of business, and then, somehow, they fall in love.

You’ve Got Mail is considered an archetypal romantic comedy, but it is at its heart a film about technology—about anxieties surrounding the Internet and the ways in which it impacts our lives and our interpersonal relationships, even before we were all Tindering our lives away. This is underscored immediately in the surprisingly edgy opening credit sequence, which begins with a collection of electronic sounds: beeps, clicks, ringing tones, and something that sounds like an electrocardiogram. The following scenes are peppered with jokes about the limits of digital communication: “I tried to have cybersex once but I kept getting a busy signal,” etc.

meg ryan sitting at her computer

Technology is both feared and eroticized throughout the film. The AOL dial-up tone, an icon in its own right, is like a kind of foreplay—”I wait impatiently as it connects” says Kathleen lustily—culminating in the “orgasm” of the digital voice announcing that you have, indeed, got mail. Later on in the movie, when their e-ffair is on a short hiatus, the computer itself becomes an objet petit a—an unattainable object of desire—with both characters gazing at their laptops longingly as the machines, in response, remain silent, unanimated, disconnected.

For all its modern inflections, You’ve Got Mail is like a Shakespearean tale of mistaken identity, as if Nora Ephron said: “Twelfth Night but make it early Internet.” After meeting in an over-30s chat room, Kathleen and Joe decide to have a zero-context conversation via email, using the screen names “shopgirl” and “NY152” respectively. They, like all Twitter users, have found a way to broadcast their witticisms to strangers without real-life reverberations, which is all anyone ever really wants in this modern world. The dramatic irony kicks in when they meet in person, loathing each other on-sight without realizing to whomst they loathe, in a “my only love sprung from my only hate” sort of scenario.

email from You've Got Mail

(Joe likes quoting The Godfather, which almost gives the game away to Kathleen that Joe and NY152 are the same person, until she correctly remembers that all white middle-aged men quote The Godfather and decides it isn’t suspicious. Other than that, they just talk about New York things, like coffee and the weather.)

An unfortunate power shift occurs when shopgirl and NY152 agree to meet at Cafe Lalo—a by-all-Yelp-accounts disappointing Parisian-style establishment on the Upper West Side that got #MeTooed in 2014, almost went bankrupt in 2016, and seems to owe its continued longevity to how charming it looks in this two-decades-old film. Joe, arriving second, sees Kathleen sitting there alone, figures out that shopgirl was Kathleen all along, and decides to let her believe she’s been stood up. He then arrives (as Joe) to bully her about it; it’s one of those “oh, sexual harassment used to be considered romantic” moments.

tom hanks and meg ryan

Kathleen thinks this is all an unhappy accident and unknowingly hits her inamorato with the Seussian jibe: “If I really knew you, I know what I would find: instead of a brain, a cash register, instead of a heart, a bottom line.” She then proceeds to beat herself up about being so mean.

This all happens while both are otherwise betrothed. Kathleen has a sexless relationship with a writer called Frank (played by Greg Kinnear). It is unclear that they are even intended to be more than friends until they sit down at a cafe for a meaningful chat that ends in a mutual breakup. It seems like Frank is going to come out in this scene and I have anticipated that every time I’ve seen this film. Instead, he says he fancies a Republican, which is the same thing as coming out in certain circles. Frank is a traditionalist and represents the “old” in the old/new dichotomy the film creates: he collects typewriters, bemoans the existence of computer Solitaire, and writes cultural outrage criticism with the help of the works of Heidegger and Foucault.

Joe, in turn, has a live-in girlfriend, thoroughly modern Patricia, played by Parker Posey, who is one of my absolute favorite movie archetypes: the evil brunette intellectual. She wears all black and drinks espresso so you know she is a Total Bitch. She is a book agent who, according to Joe, “makes coffee nervous,” but she actually seems totally fine until she screams at Joe in the elevator three-quarters of the way into the film, which leads to a breakup that nobody mourns. She takes sedatives to sleep, and is the neurotic ambition to Kathleen’s sentimental optimism (i.e. the only two types of women).

The sets in the movie are like if Nancy Meyers was Goth, with black instead of cream, and brown instead of…all the other shades of cream. True to the sensibility of contemporaneous shows like Sex and the City and Friends, Kathleen’s apartment is enormous for someone with an independent bookstore salary, and has a rustic, kooky-aunt charm. In this universe, clutter equals joy, and the iconic Shop Around the Corner set—arguably the best part of the entire film—is eventually stripped of all joy when its fairy lights, autumnal leaf arrangements, children’s toys, and yes, books, are sold off in the Fox Books-necessitated fire sale.

Kathleen and Joe have their first confrontation in another memorable literary setting: a chic book party that defined everything I thought I knew about publishing. Parker Posey is in her element here so you know it must be evil. Even Kathleen, who thinks “daisies are the friendliest flower,” wears a black mock-neck in this scene, and her gay boyfriend wears brown corduroy to prove that he’s a Serious Writer. With floor-to-ceiling books, mahogany surfaces, champagne, and caviar (as a garnish), it is a far cry from my own experience of the New York publishing world. Thankfully, the bookish intellectual aesthetic outlived the industry itself.

More affronting in this movie than its consistently gorgeous weather (making me nostalgic for a time when New York had more than two seasons) is its ending: River Park West is in full bloom and Joe, after callously undermining Kathleen’s beloved 42-year-old family business and then deceiving her for a number of months, chooses to finally reveal himself to be her email suitor. Kathleen, despite aforementioned facts, is overjoyed. They kiss, Joe’s Golden Retriever inexplicably stands up and hugs them, the credits roll, and…then what happens?

Kathleen doesn’t have a job now but I guess…she doesn’t need one? She’ll just live with Joe in his soulless apartment while he crushes more mom-and-pop shops? What happened to her sentimental critique of Big Business?

The winner of this movie is capitalism. Jeff Bezos creepily opens physical stores after shuttering the ones that existed before, Elon Musk gets to sleep with Grimes for some reason, and everyone sells their soul for next-day delivery. I’m struggling to see how this is romantic, but, as Sylvia Plath said…every woman adores a fascist!

Lizzi Sandell is a writer/editor from London who lives in NYC.



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