I remember the first time I went online to talk to an object of my affection. The platform was AOL Instant Messenger, I was in ninth grade, and the object in question was a boy a year older than me who was so crush-worthy that I physically couldn’t figure out how to form words in front of him. I went painstakingly out of my way to get a hold of his screen name, and once I did, I messaged him to tell him that I liked his band. All I remember of his response was that it was typed in 10-point orange Comic Sans MS font, and that it quite literally sent me spinning out of my chair and through my house in excitement. I was hooked.

Since then (when I thought it was cool to wear not one, but two, popped collars) I’ve felt many of the same adrenaline rushes upon receiving text messages, Facebook messages, and emails from guys on whom I’ve wasted too many hours thinking about. And I know I’m not alone in my excitement—I have a friend who admits that some Facebook notifications have a tendency to make her heart flutter.

I blame my faith in the power of the digital message on my lifelong obsession with You’ve Got Mail. A resident of the Upper West Side, I’ve curated the perfect “in the steps of Kathleen Kelly” tour of my neighborhood. I’m also somewhat of an introverted old soul and feel a kindred spirit to middle-aged women who wear sweater sets and live by the rules of Pride and Prejudice. You’ve Got Mail introduced the digital sphere as an acceptable means of getting to know someone.

In the fifteen years since You’ve Got Mail has come out, the online world has undergone such a radical transformation that we no longer have to turn on our computer and dial-up to check for new mail. We live in a world of mass communication, one in which we can virtually contact anyone, anytime, anywhere. The screen is a new form of comfort zone, and we use it to say things that sometimes we’re too inhibited to speak aloud. Such constant communication makes it almost too easy to articulate ourselves to our potential main hangs.

A few months ago, I received a text at 2 AM. Its author had begun a habit of texting me in the wee hours of weekend mornings, and he had evidently interpreted my prior nonresponses as encouragement to up his game. Half asleep, I looked at my phone and saw a line of illegible characters in a foreign alphabet. I went back to bed after immediately thinking, “What the fuck?”

After waking up on Sunday and telling my roommates about the cryptic message, one of my friends suggested that I type it into Google Translate.

“It’s probably what he wanted you to do, anyway,” she advised me in the way that friends do when they indulge each other in these matters.

I copied and pasted the text into Google Translate. After a few seconds, the sentence, “you’re a really pretty girl” appeared in the right-hand box.

“What the fuck?” once again, was my initial response. Was I being courted, and was this complement part of the wooing process, or was this a less generic, albeit creative, way to initiate a booty call? The sent time of the message and the presumption that its author had imbibed the current alcoholic beverage want by college-aged hipsters steered me towards believing the latter.

Rather than feeling flattered that he thought I was pretty, I was annoyed. It was the same annoyance that women feel when they walk down the street to a chorus of catcalls. In the context of a late-night text message, this guy’s intended compliment was seen as an invasive way to lure me to his room.

The text has joined a growing inbox of other messages that have failed to make my heart flutter. Instead of creating an intoxicating adrenaline rush, these messages now fill me with a sense of frustration towards dating. And so I worry. Have late-night texts and the intention behind them tainted the act of digital correspondence that You’ve Got Mail rendered so romantic?

Then again, think about it: NY152 didn’t profess his love to Shopgirl over the internet. In fact, he didn’t say anything remotely romantic over e-mail. He saved the good stuff—the cliché lines that make romantic comedies so squeal-inducing—for a personal, face-to-face interaction. So when romantic gestures are limited to the digital sphere, when do they stop being seen as charming and start being construed as sleazy and creepy?