On speaking to strangers

It’s every girl’s dream*: the meet-cute in the park with a handsome stranger. He becomes inexplicably smitten and whisks her into a world of glamour and chic cocktail parties and weekends in St. Bart’s. The modern fairy tale, brought to you by Gossip Girl and unrealistic millennial aspirations, n’est pas?

But how does she know, at first, that he is who claims to be? What proof do we ever have of identity?

*Not actually every girl. Only basics like me.

Strangers are everywhere, of course. We operate on either side of a thin line: ignoring those we don’t know, or taking the leap of making a connection. Usually, that thin line is a threshold—literally. Step inside a restaurant or bar, and boom—everyone in the room is on-limits for conversation. Step back onto the sidewalk, and New Yorkers avoid dreaded eye contact at all costs. Place denotes identity in our society. In the city’s whirlwind of anonymity and dense humanity, location is all we have to cling to when we’re trying to figure out the people around us. That’s why we ask the rote questions: where do you live? Where do you go to eat, to drink, to work out? We relax only when we’ve pinned someone down on our mental maps. There’s a story to tell here, and it’s about class and money and how much we’ve tied social identity to access. It’s about how much that access comforts us, makes us feel kinship, lets us trust.

So when encounters occur outside of transactional spaces like bars or cafes, outside of the borders that contextualize a stranger’s presence and allow us to craft the rudimentary outlines of their narrative, it’s a jolt. In public spaces, we are anyone and everyone. There’s no way to tell where we’re from, where we belong. Stories are malleable; encounters are fate.

A few weeks ago, I found myself locked out of my apartment. It was one of those sticky, golden early fall evenings and my roommate would be home soon, so I trotted off to Washington Square Park to waste some time people-watching. I stretched my legs on a bench, observed some squirrels, checked my Instagram.

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Not Washington Square Park, but same sunset vibe.

“Excuse me, do you know where NYU is?” a stranger asked. I glanced up. He was a bit scruffy: baggy pants, scuffed sneakers, beginnings of a beard. He carried a Whole Foods shopping bag in one hand and a briefcase in another. I half-registered his question and replied offhand that it was “pretty much all around.”

“Are you a student?”


“But you live around here?”


“Do you like this neighborhood?”


“And what do you do around here?”

“I’m sorry, but I’m not in the mood to chat.”

Usually, that’s a line that works. I went back to my phone.

But not so fast. A switch flipped in him; he began to yell.

“… and here I am, just trying to make conversation, be nice, I thought maybe you were homeless, I was going to give you some money, but no, you are just going to write me off like this?!”

The performance of his anger was expansive, almost laughable in the drowsy evening. On the light-dappled lawn behind me, a woman in a lawn chair went on reading her book. Across from me, a couple of tourists licked their ice cream cones, nonplussed. He was acting out a different script, disrupting the scene the rest of us were playing so placidly. Whatever, I thought, I was here first—and I had nowhere else to go. Better to smooth it over, let him move on.

“I didn’t mean to upset you.”

“Do you even know who I am?!” he shouted, gesturing broadly, as though the whole park should know, did know. The light was seeping out of the day. A rat scurried through the bushes next to me. I shook my head, trying to keep my face blank. This is absurd, I thought. My poker face must not have been enough, because he paused for a moment in his rant—and sat himself down on the adjacent bench.

I blinked. There was no getting out of this one now.

“Let me start over. We got off on the wrong foot, is that how you say? My name is Giovanni. Giovanni Gabbana.” He waited for my reaction. “You know Gabbana?”

“Like Dolce, the Italian brand?”

He was excited now. “Yes, exactly! I am Gabbana’s nephew. I am the heir to the brand.”

Look, I know how this all sounds. But when a foreign stranger comes up to you in a park on an otherwise nondescript day and professes to be an heir to a famed Italian luxury fashion brand, your interest is piqued. You begin to hope. Maybe this is the right stranger. Maybe this time…

He was a talker, Giovanni, and he talked for the better part of an hour. Unceasing eye contact. Classic Italian intensity, hand gestures, superlatives. I kept my responses to the minimum; where I was from, the industry I worked in. He said he was a Harvard grad, went to Columbia Business School, had been an early funder of Snapchat, founded a tech company called CyberWise. He was a socialite and a Tribeca resident; he told me his address on North Moore St, mentioned his favorite local restaurants, and said I should swing by. He had been at a fashion show with Jessica Chastain last week. He vacationed in Ibiza. He grew up between London and Milan. Would I like to join him for coffee next week? He could introduce me to some people who might help me with my career…

At 8:30pm, an alarm on his phone went off. “Ah, yes,” he said, “that’s to remind me to go home. I used to stay out very late. I was a party boy, some people maybe they think I’m a dick because of it, but I’m getting better now, I’m staying in,” and he kept going on. He gave me his email and his phone number (“…and this is not my publicist’s number, which I usually give, but my private phone, OK?”) and said that it was up to me, he knew it was crazy to meet in a park, but it was fate, I intrigued him, I was not what he expected, I was different, no Prada handbag, no pretension. I said nothing but “thank you.” Eventually, finally, he left. I blinked and looked around: night had fallen.

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Washington Square Park, shining bright.

When I got home, I Googled him. I needed to pin him down, verify his claims. If we had met in a bar, I would never have doubted. But it was the park… it was a public space.

His LinkedIn corroborated his story. I’m a former investigative reporter, though, and one source is never enough. So I dug deeper, looking for a paparazzi photo, a mention—but what I found was both terrifying and sad. He was a fraud. He had been arrested for grand larceny and locked up in 2009 for credit card fraud, accused of scamming his so-called “friends” out of hundreds of thousands of dollars to spend on partying at nightclubs and living in luxury at the Waldorf. Since his release, however, his behavior hadn’t much changed; he was spotted spinning his story in Washington Square Park to a young woman back in 2010, too.

I did not send him the email I had promised.

Right now, I’m sitting in a cafe in the West Village, listening to soft French jazz as cigarette smoke drifts in through the open windows. It’s 4:30pm on a weekday afternoon, and people are thinking about a glass of red wine.  

But I’m thinking about the threshold, the thin line, between the sidewalk and the cafe, and how I always believed in its ability to connote identity, and how maybe that trust is misplaced. I’m thinking about the difference between Giovanni and the man sitting next to me in his navy cashmere sweater, MacBook out. I’m thinking about how we make strangers familiar by association with places and things.

I’m also thinking about how Giovanni tricked me; about how careful we have to be about trust; about how the stories people tell are not necessarily true, even if they say the right things. The article written about Giovanni shows he was savvy to this fact. He knew he would receive access only if he pretended to have it already. He knew I would speak with him only once he signified that he was worthy of being spoken with. He could no longer pay for tables at a nightclub, but he could still convince me that he belonged there, with a glass of Dom Perignon in hand.

There is a difference between the stories we tell and the truth as it is. In a conversation with strangers, we surrender our ability to discern that difference. We accept that fantasy and reality might coexist. It doesn’t really matter if we are in a restaurant or on the street, after all. The restaurant just requires that we pay for the illusion of safety, of belonging, of trust. And what is money but an illusion of its own?

So if the man in the navy sweater said hello, I’d say hello back. And I’d have that chat with Giovanni again. Speaking to strangers is half the fun of this city. It’s how I learn my responses to the unknown; it’s how I step outside of my comfort zone. The only barrier is my own sense of superiority. The only fear is that the stranger will be crazy. And if he is, like Giovanni? The story speaks for itself. There is no fairy tale without risking an adventure.

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Strangers all around.