The Thrill of Putting Yourself Out There

Five women walk into a bar...

Illustration by my Tuesday dinner date, Nicholas Konrad.

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I. A New Social Experiment: Napkin Night

Two Fridays ago, I met four friends for a fancy dinner and a dating experiment we’ve started calling Napkin Night.

The idea is simple: You gather a group of single friends to go to a series of bars and at each one, someone in the group has to hand a person a napkin with their name and phone number on it.

If this sounds like the kind of thing a bunch of middle school girls might dream up at a sleepover, that is exactly the point.

It turns the solitary and sometimes depressing act of looking for potential matches, into a communal one. It is just as much, if not more, about being spontaneous with your friends, as it is about meeting someone you might actually want to date. And maybe most importantly, it pumps adrenaline and playful stakes into the act of expressing interest in someone for the first time. Something that is sorely missing from my practice of tapping off a like and a “hey how do you get your hair so swoopy?” from the comfort of my bed.

So last Friday, I showed up to dinner with a sharpie marker in my coat pocket, and a manic level of determination to get everyone to participate in this new social experiment. In my mind, the main challenge was going to be logistical: the ink in the bar pen would run out, or our napkins would be too wet from the rings of our drinks, or all the people we’d meet while out would be over the age of 50.

That turned out to be magical middle-school-like thinking too. In reality, the obstacles we faced were much more ill-defined: Some of us were kind of sleepy, we all mainly wanted to hang out with each other, and we didn’t know where to go out. We had competing memories of which West Village bars were tolerable and competing opinions about where single men spend time.

One person’s theory - that single men watch sports and lean casual to divey in taste - led us to a crowded basement level bar where everyone looked about 25.

It was easy to meet people there. I turned around for what felt like a minute to ask Sophia and Natalie a question and when I turned back around, Mary and Audrey were being handed beers and exchanging Venmos with a sweet guy who told us he had shown up at the bar alone after catching a comedy show in the area with a friend.

A few minutes later, I noticed three guys leaning against a back wall who seemed to be continually glancing in our direction. I asked my friends for their bets on their age and then went up to the trio to get the correct answer: They were all 27. One was gay, one was in a relationship and one was straight and single.

We all chatted for a bit, exchanging stories about where we lived and how our respective friend groups had met. (They met when they were living in San Francisco working at the same company.) And when I told them about my newsletter, they pretty quickly offered up their takes on dating. According to them, it’s easier to date as a man in NYC than it is in SF, and easier especially for straight men who can date women well out of their league. I laughed a lot at this at first, and then less as it became clear it wasn’t a joke, and started to resonate with my reality.

Then it was on to the next bar. We went to Due West where there was a cover that none of us were willing to pay. Then to The Garret where the bouncer wouldn’t let in Audrey, who had left her license at home and only had a photo of it on her phone. Then to Galway Hooker, where it was so crowded, we got separated mere moments upon entering the bar and had to text each other: “Meet outside!” to regroup. Finally we made it into Blind Tiger where the Jake Paul - Mike Tyson fight was playing on at least 3 different TVs and the crowd was overwhelmingly male.

It could have been perfect. The bar was packed so tightly with men our age, it was nearly impossible to move, much less order a drink. There was just one problem: The men in this room were paying approximately zero attention to women.

It was almost like entering an alternate reality where everyone existed in a Hobbesian state of nature. The men were so high off the excitement of impending violence that some of them were acting as though they themselves were about to enter the ring to fight. When the TV screens froze, as they did for people all over the country, some patrons stood on stools and yelled at the bar staff to fix the issue. When the bell rung out at the start of each new round, people in the bar called out instructions for Mike Tyson to destroy Jake Paul.

There was an undeniable pull to the room. I found it simultaneously fascinating and repulsive. I couldn’t quite bring myself to leave, but my desire to approach any more strangers that evening shriveled silently inside of me.

In the end, I hugged my friends goodbye and made my way to the subway without giving out a single napkin.

II. The World Before Dating Apps

On one hand, the experiment was obviously unsuccessful. None of us asked anyone out.

On the other hand, we all agreed it had been an unusually fun night, even with the slightly unsettling environment at the end. (One of my friends even had a cute exchange over Venmo the next day with the guy who bought us drinks at the first bar. He sent her $00.02 with a message to the effect of: “I think we’d like hanging out one on one. Just my 2 cents.”)

Napkin night, it seemed, had reminded us all of how thrilling it could be to move through an entire evening open to engagement with anyone. It got me thinking about what life must have been like before dating apps — when people were habitually striking up conversation with strangers when out, and there was a richer creative culture surrounding how to meet potential romantic partners.

I am among the first generation to have come of age in a dating world dominated by apps. I was a junior in college the year that Tinder hit 10 million users — the year that single adults walked out of a bar one night, not realizing that their chance of meeting someone in person would never be as high again. Back then, everyone I could possibly want to date I met simply by waking up and going to class. But by the time I entered a setting where I wasn’t surrounded by single people every day, dating was overwhelmingly mediated by algorithms.

I often wonder about what I missed. The creative practices, the games like napkin night, that must have once been common place. The strange places that radiated with the potential for a romantic encounter (the office! the grocery store!) that no longer seem to hum with the same energy. For all the endless talk of how dating apps have changed modern dating, this is probably the thing I mourn the most.

III. Onward!

But of course, we can’t go back. We can only go forward.

What I’m most excited about today is not the movement against dating apps, but rather the recognition that we can reap their benefits without being singularly dependent on them.

For all the myriad issues dating apps have created or exacerbated, I think they have two major strengths. The first is the most obvious: they expand our access to meeting more potential dates than was ever previously possible. The second I think gets undersold: they remind us that we are not alone. Whether or not you ever meet someone you like on an app, there is some small comfort in knowing that at any given age, in any given geographic area, there are other single people searching for connection too.

At the same time, it’s undeniable that there’s a growing interest in finding more creative, in-person ways to meet people. From niche singles mixers to speed dating events, to (dare I say) running clubs, there’s a resurgence of real-world opportunities to connect without swiping. I’ve also heard good things about apps like 222 that use technology to match groups of strangers together for an activity. And the McCaren park dating wall that lets singles essentially advertise their availability to everyone walking by. Even dating bounties, which scandalized all my friends, seem like a step in the right direction: They incentivize people, through a large cash reward, to put more effort into setting single people up with each other.

While none of these things are likely to replace dating apps, I think they’re an exciting and important development. Like napkin night, they bring back opportunities for unexpected encounters—moments that might help restore some of that magic we lost when connecting with strangers became the exception rather than the default.

Inaugural napkin night, bar #1. Our 27 year old friends and sweet guy with the Venmo are just out of frame to the right. Our photographer, a very kind woman, is yelling at a sea of people trying to enter the bar to stay put so she can get this shot.

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Oh and hey - do you want to share a dating story about yourself? My friends at the New York Times are seeking two different kinds of dating stories right now. Maybe you’d like to submit?

Modern Love wants to hear about the worst date you’ve ever been on. (Host of the pod, Anna Martin, is a reader of the newsletter!)

And Stella Tan (another friend of the newsletter!) is searching for people who are willing to talk about why they ghosted someone, for a magazine story I cannot wait to read.