‘Keeps me optimistic’: why You’ve Got Mail is my feelgood movie

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There’s a montage in the opening of You’ve Got Mail that is so sentimentally sweet that it feels like the cinematic equivalent of a pumpkin spiced latte. As the guitars of the Cranberries’ Dreams jangle, the film’s two leads, Meg Ryan and Tom Hanks, leave their respective homes and walk through an autumnal-hued New York City with smiles on their faces, their characters unaware that earlier that morning they were anonymously exchanging emails. I must have seen this opening more than 100 times, and while I’d never be so happy to walk to work, it always fills me with a romantic appreciation for life’s potential.

I can’t remember the first time I watched this Nora Ephron-penned and -directed romcom, but I do recall that as a child I would load it into the DVD player at every available opportunity. Based on the 1940 film The Shop Around the Corner, and centred on two competing booksellers – Ryan’s Kathleen Kelly, who runs her mother’s independent children’s bookstore, and Hanks’s Joe Fox, the heir to an impersonal Barnes & Noble-style mega-chain – it’s a standard enemies-to-lovers affair, albeit with a twist that these two rivals are unknowingly emotionally involved online.

Growing up, I was enamoured of the film’s depiction of Manhattan. It seemed charming, a place of small businesses, neighbourhood markets and warring bookstores. But this provinciality extended beyond an idealised vision of New York to cyberspace. When it was released in 1998, the internet hadn’t greedily consumed every aspect of our lives. Instead, it remained a curiosity, a strangely intimate place where, as they do in the film, two people from the same area could meet in a chatroom, begin emailing, and end up together.

Nowadays it seems natural that two people might connect online before meeting IRL, but at the turn of the millennium, online dating was the land of oddities and saddos, descriptions that suit neither Joe nor Kathleen. That such a connection could be found in this at-the-time-unexplored realm of the internet was hopeful to me as a gay kid whose first interactions with other queer people involved lurking in chatrooms at night. It’s also why, as I’ve grown older and weathered the rise of social media and apps like Grindr, I find myself returning to You’ve Got Mail: it may be naive and soppy, but as a single person it keeps me optimistic that genuine connection may still be found by logging on to your computer (or unlocking your iPhone).

In the film, online communication isn’t reduced to sub-tweets and headless torsos asking for hookups, but is instead a place for meaningful correspondence in the form of letters. And these letters, sent as emails and delivered as voiceovers by Hanks and Ryan, are wonderful. Here Ephron’s script offers up delightful observations about life: Starbucks, Joe suggests, is “for people with no decision-making ability whatsoever to make six decisions just to buy one cup of coffee”, while Kathleen ponders about seeing a butterfly leaving the subway “where I assume it went to Bloomingdale’s to buy a hat that will turn out to be a mistake, as almost all hats are”. If only the endless back-and-forth of messages on Hinge were as enlightening.

Still, You’ve Got Mail does have some issues. Joe’s behaviour is at best creepy and at worst sociopathic: when he learns that he’s been emailing Kathleen before she does, he withholds that information, puts her small bookshop out of business, and then engineers a friendship with her so that by the end she hopes that he and her anonymous pen pals are one and the same. Kathleen, meanwhile, appears ambivalent about being manipulated by her capitalist oppressor and is even nonchalant about whether her mother-like figure Birdie (Jean Stapleton) was romantically involved with the fascist dictator Francisco Franco: “It happened in Spain,” she says. “People do stupid things in foreign countries.” Thankfully, Ephron’s otherwise razor-sharp script, aided by the on-screen chemistry between Ryan and Hanks, means you can overlook these foibles. And when the pair kiss in the final scene, Harry Nilsson’s cover of Over the Rainbow playing in the background, the feelgood factor is undeniable.

For Kathleen it’s also an ending that feels well earned. “I lead a small life. Well, valuable, but small,” she writes in one email to Joe. “And sometimes I wonder: do I do it because I like it, or because I haven’t been brave?” By the time the credits roll, she’s been forced to find out and grabbed the opportunity for a new and potentially more expansive life. All I can do is hope for the same. Until that time comes, I’ve got my trusty DVD at the ready.