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Why You’ve Got Mail is simultaneously a classic rom-com and the worst Nora Ephron movie

By Ansharah Shakil, December 10 2023—

You’ve Got Mail is the third of the holy trinity of Nora Ephron that includes When Harry Met Sally and Sleepless in Seattle. It’s the last one, released in 1998, and fittingly considering its holiday atmosphere and original December release date, it’s showing at Globe Cinema on Dec. 13. 

Ephron, who died in 2012, was a prolific journalist, writer, and filmmaker, known for her depth, social commentary and the clever, acerbic wit that existed alongside her sentimentality. Part of her legacy is producing three of the most long-enduring Hollywood rom-coms. In her oeuvre, You’ve Got Mail is regarded as one of her impactful works, highly successful upon first release. Even now, when the title of the film and the associated ping noise have been rendered obsolete, You’ve Got Mail is still considered to be iconic. And yet it lacks the magic of both When Harry Met Sally and Sleepless in Seattle

The premise of You’ve Got Mail is about two people who fall in love online while being enemies in real life. When children’s bookstore owner Kathleen Kelly (Meg Ryan) meets the heir to a commercial chain of big bookstores Joe Fox (Tom Hanks), she hates him for trying to put her independent bookstore out of business. The two couldn’t be more different. But on AOL, under the names “Shopgirl” and “NY152”, they’ve built up a friendship without revealing any personal details. Kathleen and Joe have, like you’d expect, a perfect meet-cute. They fire sharp barbs at each other and settle into a period of deep-seated hostility, while still confiding in each other online and eventually beginning to see the good in each other in real life. 

You’ve Got Mail is witty and well-directed, with warm fall foliage, comfy layers of sweaters and endearing characters. The ever-charming Ryan and dapper Hanks are a legendary pairing, and they’re in top form here. Plus “Dreams” by the Cranberries plays over the opening montage. What more could you ask for? But the problem with the movie is its romantic resolution, and the messages that result from it.       

Hanks, who turned down the romantic lead in When Harry Met Sally, isn’t really missed there; Harry Burns is a role made for Billy Crystal, and it’s hard to imagine anyone else playing the Harry to Ryan’s Sally. In Sleepless in Seattle, Hanks is a perfect lead. It’s easy to see why someone, even someone who looks like Meg Ryan circa 1993, would fall in love with his character. But in You’ve Got Mail, while Hanks has his swoon-worthy moments, Joe ends up feeling far more smarmy than anything else. 

You’d expect the film to have Joe recognizing the importance of Kathleen’s shop to her, and fighting to help keep it open. Except none of that happens. Kathleen resigns herself to having to close the shop, Joe apologizes but doesn’t seem to regret much of his actions and for some reason, withholds the information that he’s NY152 from Kathleen for over half the movie. Despite its promising start, the romance falls flat. 

The movie’s problems, to be sure, are now dated, quaint and slightly depressing — in one scene, Kathleen struggles to pay at a grocery store because she’s accidentally stepped into the cash line, and all she has is her credit card. You’ve Got Mail is a product of its time, an artifact of the early digital age in which the internet was a place to fall in love (over email, of all things) but not much more, and when a chain of bookstores taking over an independent bookstore was the main struggle. Independent bookstores struggle to survive today, but big chains struggle against Amazon, too. It’s hard to look back at You’ve Got Mail and see, even then, the loss of Kathleen’s original rightful critiques of Fox Books. Her livelihood is compromised by her capitalist love interest. If we’re meant to see this as the best possible ending for the movie, years later I can’t see why unless it was meant to be an intentional dark commentary on corporations bankrupting small businesses. 

Despite all these bothersome aspects of the movie, You’ve Got Mail is still an obligatory watch for rom-com lovers. Its cozy, vulnerable quality makes it a perfect watch for the holiday season, and Ryan and Hanks are captivating the entire time. There is a quiet, brave intimacy at the heart of the movie. Kathleen and Joe fall in love online, yes, but not the way people search for love online nowadays, and in order to be together, they have to spend time together in person, in real life. That’s a lesson still relevant today. 
Ephron’s endings generally knock it out of the park, and notwithstanding my quibbles with this one, the last ten minutes are as heartwarming as you’d expect. Watching her three rom-coms from worst to best — You’ve Got Mail, Sleepless in Seattle then When Harry Met Sally — is the ideal gateway into Ephron’s films. You’ve Got Mail is perhaps the worst of them, but it’s the worst of a selection of iconic movies — the best, of course, being When Harry Met Sally, which isn’t just one of the greatest romcoms, but is one of the greatest movies, period.


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