To All The Boys I've Trolled Before: A You've Got Mail-Inspired Tinder Experiment

Last night, I sat on my couch messaging a 24-year-old guy — let's call him Eli — whom I do not know. Tinder told me he was three miles away and also undecided about pizza toppings — "Pineapple or no pineapple?” he asked in his bio. Pineapple, indeed.

I said "Hey," and the die was cast.

I'm no stranger to Tinder (just ask one of the many Emotionally Unavailable Guys Of Brooklyn With Whom I Have Gone On Anywhere Between One And Ten Dates), but I was newly inspired to get back in the game following a recent viewing of You've Got Mail. Like, maybe there's an affable young Tom Hanks lookalike bookstore tycoon waiting for me with a golden retriever in Riverside Park, and maybe I have to find him on the internet, fast. If Meg Ryan could do it, who's to say I can’t? So I hatched an experiment. Let me explain.

My friend Maya and I watched the movie for the first time (yes, ever) last weekend — and, throughout most of it, we laughed. Hard. Even the opening scene is funny: Doe-eyed ingenue Kathleen Kelly (Meg Ryan), who has all the street smarts of a baby bird, flits about her apartment and waits for her doofus boyfriend, Frank, to leave for work so she can power on her computer and sign into her AOL account as "Shopgirl," her breath catching on, as she puts it, "those three little words": You've got mail.

The sender is Joe Fox, a.k.a. NY152. After meeting in a chatroom for 30-somethings, the two carry on an email relationship, exchanging daily correspondences, including this absolute goldmine of a soliloquy from Kelly: "Sometimes I wonder about my life. I lead a small life — well, valuable, but small — and sometimes I wonder, Do I do it because I like it or because I haven't been brave? I just want to send this cosmic question out into the void. So good night, dear void."

Of course, the film came out in 1998, when the internet was still novel, there was no "u up?" culture to speak of, and it was okay — thrilling, even — to talk to nameless strangers on the internet. It was still exciting to get an email. No catfishers in basements yet. No, those wouldn't really enter the zeitgeist for at least 10 years. (For the record, it is and always has been dumb to make your screen name your state plus your street address, like NY152, for example.)

Despite the cheese factor ("goodnight, dear void"), there was something undeniably refreshing and nostalgic — oh, that there was ever a time when people were pure and trusting on the internet! — about the messages Shopgirl and NY152 sent back and forth to one another. A far cry from the many "good, hbu" messages we've come to expect as the norm. So Maya and I wondered: What would happen if we took a page out of You've Got Mail? How would our matches react? We'd disarm them, yes, but would we charm them?

And thus, a challenge was born: For the next week, Maya and I would communicate on dating apps exclusively with lines from You’ve Got Mail — lifted straight from the emails sent between Shopgirl and NY152. With the occasional “haha” and “hey” peppered in to retain a modicum of Tinder normalcy, of course.

So back to Eli. After we exchanged greetings, I hit him with: "The odd thing about this form of communication is you're more likely to talk about nothing than something."

At this, he told me I was “deep, homie.” Thank you, Eli. Then I tried The Void monologue. He replied by asking if I wanted to drink wine and make out. Not the point, Eli! After my third message, though, his tone changed:

“Do me a favour,” he said, “Stop quoting movies.”

The jig was up, and Eli was mad. I told him I was using You’ve Got Mail quotes on Tinder for story research, and he didn’t respond for five minutes.

Then, in what can only be described as the most savage millennial-to-millennial dating app affront ever committed, he said: “Sorry, you made me go on Coffee Meets Bagel.”

As in, he was so put off by my messages that he had to leave the app and go on a different one. But could I really blame him? To his credit, he responded to me, which is more than can be said for most of the guys I sent these lines to.

Maya's matches were kinder. When she tried the "I lead a small life" line on Jason*, he told her to just be happy.

"Maybe you just wondering too much [sic]," Jason said, followed by a winky face. "Be positive. Do you like how your life is right now?"

Jason didn't want her to stress, and at least that was nice.

Unsurprisingly, the line that yielded the most varied responses was also the most soul-baring: "What happens to me when I'm provoked is that I get tongue-tied, and my mind goes blank. Then I spend all night tossing and turning trying to figure out what I should have said, for example, to a bottom-dweller who recently belittled my existence?"

There was the apathetic: "Hard to say, I don't really know the situation." Fair.

And the affirming: "I think that's a natural human response, honestly. What did you want to say to this bottom-dweller?"

Both made me feel better about the world. The former, because he wasn’t afraid to admit what he didn’t know, and the latter, because he acknowledged the common humanity in all of us. It should be said that the former unmatched Maya moments later after she asked, “Do you ever think you’re the worst version of yourself?” But that’s besides the point.

So I guess the moral of this story is what we suspected all along: Online dating has evolved since 1998. Of course it has. And earnest existential questions on Tinder mostly beget negative or angry responses. Or concerned responses. Or no response at all.

But do we mourn this loss of innocence? I say no. The internet is scary; stranger danger is real; and I don’t think young Tom Hanks lookalikes with golden retrievers hang out on Tinder waiting to be sent long and winding paragraphs about self-identity, anyway. Keep the Tinder convo light and easy and save the void talk for the bar, is what I say. Also, if he tells you he looks like a young Tom Hanks, he’s probably lying.

And lastly: To all the boys I’ve trolled before, I’m sorry.