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Why “You’ve Got Mail” Is the Greatest Love Story of Our Time

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Every generation has their love story. The G.I. Generation had Casablanca. The Silent Generation had An Affair to Remember. And Gen-Y? We have You’ve Got Mail.

Of course, the appeal of You’ve Got Mail isn’t exclusive to Gen-Y. In fact, though the stars are Baby Boomers, it’s Gen-X-ers who would’ve had the distinct pleasure to come of age in a world where You’ve Got Mail was possible. The year of its release, I was twelve and more likely to spend my time online playing Slingo than curating a passionate cyber-relationship. Part of my fascination with You’ve Got Mail stems from my generation’s inability to experience a similar scenario firsthand. The other part: That despite massive changes in how we regard the ‘online persona’, I still relate to the films’ resolution.

Rom-coms of the pre-You’ve Got Mail ‘90s were formulaic in their account of emerging technologies. Relationships thrived off of serendipitous events, and faulty technology would constantly disrupt discourse. Our heroes and heroines were constantly leaving longwinded answering machine messages that somehow went unheard; they scrambled for change to use a payphone and always came up short. These communication-based hurdles would cause the couple to break up, but life would bring them back together; they passed each other on the street and fell in love all over again and they discovered that the devolution of their relationship could be blamed on a miscommunication of some sort. There was very little personal accountability – time and time again, technology would be responsible for the temporary rift in any given onscreen relationship.

And almost overnight, communication technologies became mobile, reliable. In the new millennium, any American film to downplay the prevalence of these technologies was being disingenuous. Aside from period pieces, it would be unrealistic to ignore the pervasiveness of cell phones and internet. The internet wasn’t the Wild West anymore.

But it didn’t start out that way. A viral video clip that emerged earlier this year reminded us of this, when we witnessed a 1994 Al Roker and Katie Couric genuinely fucking confused as to what the internet is. Filmmakers didn’t quite ‘get it’ back then either; as shown by the implausibility of The Net. I loved The Net; I watched it in full anytime it was on television. Then I got older and realized that, although the title of the film alludes to the internet, the relationship between the internet and the plot is tenuous, at best. The Net feels like a weak attempt to capitalize on a trend.

But things got better: fifteen years later, the documentary Catfish would illustrate the very real consequences of meeting someone online. iCarly, a TV show about a tween with a web show, would become the standard for Generation @. Onscreen and off, the human and the internet would become indistinguishable.

But between these two easily identifiable time periods is a grey area. And the existence of that grey area is what allowed You’ve Got Mail to happen.

It might be hard to remember, but there was a small window of time in which people could exist both on and offline without their two personas being intrinsically linked to one another. The offline self didn’t exist online. The online self was the offline self amplified – and anonymous.

Nowadays, online anonymity is for people who genuinely believe that no one can come along and blow the lid off of the entire thing. Senators who troll Craigslist for cabana boys, for example. But during the You’ve Got Mail era, there was no way to be but anonymous. After all, you didn’t know what kind of ‘freaks’ you were dealing with online. What if someone stole your identity, like in The Net?

So we have Kathleen Kelly/Shopgirl and Joe Fox/NY152 – archenemies IRL but obsessed with each other online. Online dating isn’t alien to our generation, and I’ll be the first to admit that it’s still possible to fall for someone’s internet persona. But the difference between the modern online crush and the relationship that blossoms in You’ve Got Mail is that their relationship depended on anonymity, and ours would never flourish under similar circumstances.

Why not? Because on a dating website, we’re not keen on conversing with people who don’t have a photo. We assume that anyone technologically inclined enough to be on a dating website should have at least one photo of themselves. If they don’t, logic follows that they’re hiding something. In 2011, lacking an online fingerprint isn’t regarded as cautious; it instead breeds distrust. But the nature of the internet was different in 1998 – there was nothing suspicious about Shopgirl and NY152 agreeing to withhold identifying details. A lack of detail was the norm, not something to be feared.

Unlike Shopgirl and NY152, our personas are one. We can be Googled, or Facebooked, or followed on Twitter. Our real selves have online representation. Even if you should meet someone in an online scenario in which you’re anonymous (say, a message board or the like), the mystery disappears as soon as you divulge your full name.

NY152 faces this dilemma when he arrives for what he believes will be his first offline meeting with Shopgirl. He discovers Shopgirl to be Kathleen Kelly, his business rival. Both online personas were playing by the rules up until this point. They were following the internet etiquette of 1998. They didn’t choose to be anonymous because they were pretending to be something they weren’t. They were using the internet with caution because that’s what made sense.

Just before seeing Kathleen as Shopgirl for the first time, Joe admits to his friend that Shopgirl could very well be the love of his life. Discovering her identity put him in a vulnerable position. In a moment of panic, he approaches Shopgirl not as NY152, but as Joe Fox. What else was he going to do? Walk over and say, “Hey Shopgirl, I’m the virtual man of your dreams – by the way, my bad on putting you out of business. Sauvignon Blanc?” He’d already made Shopgirl fall for NY152; now he had to make Kathleen fall for Joe.

And fall she does. Joe dials down the online romance and focuses on building an offline relationship with Kathleen, simultaneously painting NY152 to be a freak or a flake, depending on the day. It starts with a visit to her apartment when she falls ill, it grows with a number of lunches and walks in the park, and it culminates with Shopgirl and NY152’s long-awaited “first date” in the park in which, upon realizing that Joe and NY152 are indeed, the same person, Kathleen tearfully admits, “I wanted it to be you, so badly.”

“I wanted it to be you, so badly.” This line allows each and every one of us to live within that grey area; it allows us to revisit the brief moment in history when technology was neither working for us or against us. It is one of the most relatable feelings to result from the advent of the internet. Kathleen says this literally, and though it’s unlikely that we’ll discover the person we love online and the person we love offline are one and the same, the sentiment remains: You are the person I fell for. Sometimes, we fall for someone’s words, but that’s all. They don’t look or smell or touch or taste the way we’d imagined. Meeting someone we’ve fallen for online who translates into someone we can fall for offline gives us more than a sense of relief; it gives us hope that we’ve found something that transcends lust, something real.


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