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Photograph: Courtesy CC/Flickr/Kevin Case

Here's what happens when you spend a week chatting up 35 strangers in New York

By Lindsey Sullivan

People flock to New York for a variety of reasons. (Here’s 50 if you’re having one of those days where you got stood up by a date, or worse, the MTA.) New York’s food, art, landmarks, traditions and attractions hold infinite possibility for everyone from the wide-eyed newbie to the born-and-raised naysayer. But the greatest thing about New York is the people who make it what it is: a constantly humming hub of cultural phenomena, from Hamilton to the cronut. People come to New York to experience these near-impossible dreams; they stay because of the people they can share them with.

So, if this city’s endlessly interesting population of inhabitants is the basis of its lasting appeal, why is it that starting a conversation with a random fellow New Yorker is so terrifying? 

Having moved here in April, I began asking myself this question on subway platforms and in coffee shops. Sure, I have great friends, roommates and co-workers to spend my time with. I have been described as “friendly” and “extroverted.” But when it came to chatting up people I didn't know, I would freeze and find excuses: “They look busy” or “Eh, I really like the song that just came on my shuffle anyway.”

A friend of mine from college strives to talk to five strangers a day. “Because you never know!” he said when I once asked him why. I was fascinated when he shared this daily ritual with me, and wanted to try it out. There were some rules: I couldn’t meet any of the whopping 35 strangers (that’s five strangers every day for a week) online. Getting introduced to someone on Tinder and Bumble would be cheating. I had to try to keep things fair by varying the ages and genders of those I would approach and where I would approach them (Read: I couldn’t just tell every fellow fierce chick on the subway that I liked her shoes.) I also had to have more than two “back-and-forths." For example, if I said “sorry” to someone for bumping into them in the street and got an “all good/eff yourself” back, that wouldn't count.

I started on a Sunday morning and was shocked at how nervous I was to start my task up each morning for the next week. I had no idea how to determine who would be a good candidate to speak with, what would be an effective opener or how each person would react. My fear was one of the biggest takeaways from the experience—especially when I felt fantastic after speaking with each stranger. I was especially apprehensive about approaching men. As a young, heterosexual woman, there were a bunch of reasons talking to dudes makes me particularly anxious: My middle school dance nerves kick into high gear around cute guys. Don’t get me wrong, I’m an effing delight once I feel comfortable talking to a guy. It was just getting comfortable that seemed so difficult.

Discomfort also plagued the potential for conversations with males I wasn’t necessarily romantically interested in: What if they thought I was hitting on them? What if they said something gross? Or worse, what if they tried to do something gross? It sucks that we live in a world where justifiable fear is a reason women and men don’t bother meeting in person.

However, there were some far more positive takeaways than the fear.

For one, I simply left my apartment more. It’s easy to get into the habit of working and then staying cozied up at home; New York simply becomes a backdrop to our office time and errands as opposed to a place we venture out and experience.

On Sunday, I took a Zumba class in Hudson Heights; the instructor and I chatted for a while about her day-job as a math teacher at a high school in the city (“ it really like Gossip Girl?”) and how she was obsessed with her new place in New Jersey (Seriously!). I also met an older woman who had already walked across the goddamn George Washington Bridge that morning. Later that same day, I went to Trader Joe’s, where I dubbed the gentleman giving out cheese and cracker samples “The Cheese Cracker Fairy.” He was very pleased.

Monday night, having exhausted my subway chat-ups (and realizing talking to people on the subway on a Monday morning is the worst) I took the book I was reading to my local coffee shop, chatting up my barista and a couple that was sitting by me working on a video project. I hit up the High Line, Washington Square Park and (my new favorite place to chat up dudes) The Strand, three places I hadn’t set foot at all summer, to talk to a slew of strangers. I even tried a stand-up comedy open mic (arguably wayyy scarier than talking to 35 randos) and came out of it with a new friend.

My most bizarre conversation openers were always rewarded. The cop outs that were “Hey” and “I like your shoes” usually led to stale small talk or only got one back-and-forth out of the stranger I was wasting time on. My best openers of the week? “Does that book actually say ‘assholes’ on it?” and “I’m kind of obsessed with Stanley Tucci. Can you help a sister out?”. Both were said at The Strand; a bespectacled chick was buying Assholes: A Theory of Donald Trump for her boyfriend (awww) and my quest for The Tucci Table was met with a conversation about favorite movies from the super cute information desk guy.

“I’m obsessed with your dress” worked way better than “I like your dress” when it came to breaking the ice with the ladies; I basically became a Casanova. I can now chat up any girl, any where, about pretty much anything. One of the smoothest tricks I learned? Offering to take the photo of a girl (and her group of pretty friends) struggling to snap the perfect selfie. This trick also worked wonders on a super cute family from England trying to take a picture with their adorable kids in Times Square. 

I parked myself curbside by outdoor seating areas of restaurants: “Hey! I’ve been meaning to try this place. How is it?” I asked cashiers who rang me up what they did when they weren’t at work and whether customers had been treating them nicely today. I also spent a great deal of time inside my head feeling apprehensive: What am I going to talk to this person about?

Luckily, another takeaway I had during my week of bothering people was this: Every person is New York has a prop. It could be a guitar case or a book, a dog or a killer lip color. For me, cool lunchboxes (“Thanks! It’s called a ‘PackIt.’”), a “Happy Birthday!” balloon (“I’m 27 today! My co-workers gave it to me, so I’m bringing it to dinner with me.”) and even a cockatoo (“Give me your email address! I’ll send you the e-vite to Lolo’s birthday party next week!”) were just a few of the conversation starters that serendipity presented. (For real: I met a guy in Washington Square Park that had a pet cockatoo on his shoulder. Her name is Lolo, and I was invited to her birthday celebration and encouraged to bring friends next week.)

Everyone in New York is constantly performing in character, some trying to stick out just as firmly as others hope to stay n the background. It can be as simple as a Trader Joe’s bag or an iPhone case; there is always a way into a conversation. Once you find that way in, it’s all about the delivery: are you genuinely excited about talking to this person? Or are they just another person you need to check off your list to make that deadline? Is what you’re commenting on really any of your business, or are you just trying to get a reaction to say “Hey, I’m so cool I talked to a stranger”? It’s important to realize that in taking the brave step outside of your bubble, you are stepping into someone else’s; their mood, experiences, victories and fears from the last week, last day, last hour are just as valid as yours are. In speaking to my 35 strangers, I began to remember: these are people, not just the creatures I avoid eye contact with as I flick through the photos of my Instagram feed (which, let’s be real here, hasn’t changed a bit between the 125th and 86th Street stops).

Going into this experience, my goal was to be completely confident in approaching anyone as the last day of my week rolled around. I had so many tools: locations, openers, a far better sense of paying attention to detail, even as I zoned out at the grocery store and on my way to the bank. The last stranger(s) I spoke with offered the quintessential New York moment that I was looking for. My roommate and I headed out to the neighborhood watering hole and after a drink with a boisterous group became invited to a birthday party that brought us to another bar on the Hudson and into several conversations with new friends whose numbers we were able to grab before calling it a night. Turns out, a fellow friend, a Saturday night and liquid courage are the perfect ingredients for chatting up strangers in Manhattan.

As I look back at my week, the one thing that sticks out is that every time I talked with some new it left me feeling better. I’d feel less lonely, more optimistic or—at the very least—absolutely entertained. To be sure, talking to strangers is scary. But if I hadn’t tried, I wouldn’t have a few new friends, a killer lunch box recommendation or an e-vite to a cockatoo’s birthday party in Washington Square Park for next weekend.

Lindsey Sullivan is a writer and professional theater dork at She's geeking out 100% of the time. Nerd out with her here and on the Twittah. 


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