A Year of Talking to Strangers
For the past year, I’ve hosted a meetup dedicated to having “interesting conversations.” On one Sunday afternoon a month, I gathered random New Yorkers in a public space to discuss life’s bigger topics such as love, identity, purpose, and happiness.
I started the meetup to fulfill a craving for deeper conversations. And for some reason, I felt more comfortable sharing my innermost thoughts with complete strangers than with friends (which probably also explains why I write online…).
The format of each meetup was the same. I divided attendees into groups of 4-6 people and gave each group a list of pre-written questions split into three sections.
“Past” questions tackled your childhood and how you were raised.
“Present” questions asked about who you were today and what you believed today.
“Future” questions focused on what your goals were and where you see yourself in the future.
So if the meetup topic was “Love,” a Past question could be “What was your first crush like?”. A Present question, “Do you believe in love at first sight?”. And a Future question, “How do you want to change your approach to love going forward?”.
Each 4-6 person group would discuss the first set of questions for thirty minutes before everyone regrouped to share any insights gleaned from their smaller group discussions. This process was repeated two more times with the entire meetup lasting approximately 2 hours. The format was meant to encourage rich intimate discussions while still building a broader sense of community.
By now I’ve facilitated dozens of discussions and met hundreds of people. My biggest takeaway is that we are more similar than we think. We are all human and we all have the same range of emotions. So while none of us share the exact same experiences in life, we can usually still relate to where other people are coming from. We have all known love and heartache, joy and disappointment, pride and frustration. As a result, I wanted to share some of the themes I saw across my meetups. I hope this article helps someone out there recognize that they’re not alone in what they’re feeling.
Anyone can be lonely.
We met at 60 Wall Street Atrium, a public space known for its massive trelliswork pillars and fake palm trees. I wish I had known the space was also known for its lack of heating because when I arrived, the attendees who were already there were tightly bundled in their winter coats.
The day’s discussion topic was “Friendship.” Seated in my group was a man in his mid-40s named Mike. To be honest, I was a little annoyed with Mike. As everyone else introduced themselves, Mike was entirely focused on his phone.
We started the first question, “What were your friends like growing up?”. Everyone else shared stories about their childhood friends but Mike never looked up. Suddenly Mike was the only person left who hadn’t said anything. We all turned to him, and noticing the silence, Mike finally put his phone down.
“So is this like a group to make new friends or something?” Mike asked.
Mike clearly hadn’t read the event description. But I was also surprised that a person who appeared as connected as Mike was looking for new friendships.
I explained that while friendships can develop from the meetup, the primary purpose is to discuss the topic of friendship.
“But are you looking to make new friends?” I followed up.
“Yeah, well it’s just that I lost all my friends,” Mike responded in a matter-of-fact tone.
I wasn’t expecting that response. I asked Mike if he would be willing to elaborate.
“All my friends just ended up getting married, moving to the burbs, and having kids. So now I don’t have any friends left.”
“But that doesn’t mean you aren’t friends anymore,” someone else offered.
“Well, it certainly feels that way when nobody wants to hang out with someone who is 40 and single. Nobody wants to just go to a bar and grab a beer anymore,” Mike replied.
“And then I had a really close friend until recently,” he continued. “But then he did some dumb sh*t and wanted me to lie for him to his girlfriend. And I didn’t want to be put in that position so I told him no and that pretty much ended that friendship.”
I felt the bitterness in Mike’s voice. I could also relate. By the end of 2022, a lot of my friends had also left the city. Either because of work, family, or just to live somewhere with less absurdly high rent, friends I had known for years suddenly moved out of my life. And while I still consider them my friends, and we do keep in touch, the relationships just aren’t the same.
Mike’s story reminded me how pervasive loneliness is. We tend to think of loneliness as the absence of friends or loved ones. But my meetup made me realize that loneliness is more nuanced than that. Loneliness is when you don’t feel like anyone gets you. You can have lots of friends but if you don’t feel like anyone understands you, you’re still destined for loneliness.
At the same meetup was Daniella, a young adult in her early 20s explaining how lonely she felt despite living with her childhood friends. “I just got my first real job and I want to improve my life,” she elaborated, “but my friends continue to act like kids. I feel like I don’t know them anymore.”
Mike and Daniella’s pain wasn’t just from spending less time with their friends, but also because they felt like they no longer knew their friends and their friends no longer knew them. Loneliness is not based on the quantity of your relationships, but the strength. One strong connection can erase loneliness in a way that being in a room full of friends sometimes can’t.
So anyone can be lonely.
Answers are rarely the answer.
The topic was “Identity.” We were in the “Present” section discussing whether we should always be true to our identity or whether it was sometimes okay to hide our true selves.
Jessica, a Black woman in her 30s shared. “I constantly police how I behave at work because I don’t want to play into the stereotypes of my race or gender. I intentionally act calm and rational to avoid being dismissed as a loud black woman. Even for this meetup, I spent an extra 30 minutes planning what I would wear to appear approachable.”
There was a noticeable silence as everyone processed what Jessica said.
Finally, another attendee spoke up and quietly said, “I’m so sorry. I couldn’t even imagine what it’s like to analyze every decision like that.”
Jessica gave a fantastic answer.
Jessica also didn’t answer the prompt.
When I first started the meetup, one of my goals was to provoke some healthy debate. While I didn’t want to start any heated arguments, I did want to start some lively back-and-forth discussion.
That did not happen.
Participants were less interested in directly answering the prompts than in sharing their experiences and listening to the experiences of others.
Kevin, a young adult in his 20s, disclosed how he was experiencing a crisis of identity as he struggled to navigate between being “Asian” and being “American.”
Sofia, a Russian immigrant in her 30s, discussed how her recent divorce made her question her identity now that the reason she moved to the US was taken away.
Josh, a man in his 40s from Queens, discussed his experience in New York where everyone’s identity seemed tied to what they did for a living. Josh admitted he would sometimes inflate his job title to gain the respect of those around him.
Hearing different experiences was fascinating but most attendees, myself included, usually left the meetup with the same opinions that they came in with. So at first I was dismayed. What’s the point of hosting a conversation meetup if there wasn’t any substantive conversation? But as I hosted more events, I noticed the same people came back month after month. Why were people coming back if they weren’t learning anything?
I remembered something an attendee told me at my first meetup. The meetup had just finished and I was thanking everyone for attending when an attendee profusely thanked me in front of the group. I was a little embarrassed since I didn’t think I was doing anything great and I said as much. However, the attendee insisted I was making an impact.
“You’re building community,” she said, “And that’s unbelievably important.”
People weren't coming to my meetups to get answers. People have books for that. People have Google for that. People now even have Chat-GPT for that. And if we’re honest, there aren’t real answers for the topics we were discussing.
Instead, people were coming to the meetup for the other people. People were looking towards each other for strength, to feel less alone, to hear stories, and to be heard. So the meetup topic didn’t really matter and the question prompts really didn’t matter. “Answers,” weren’t what people wanted, “people” were.
We all want our experiences to mean something.
The topic was “Crossroads.” The question was “Have you ever been at a crossroads in your life before?” As soon as I read the question, Mark, a man in his early 50s, jumped in.
“I was on Wall Street for a while. And while the money was great, I was miserable. I hated getting out of bed every day. One day I asked myself what I was doing this for. I couldn’t come up with a good answer! So I decided to quit my job and pursue something I have been wanting to explore for a while, acting. And that’s what I’ve been doing for the past year.”
Mark was not done.
“What I realized is that the voice in our head tries to trick us. It makes us believe things that aren’t true. The voice in my head told me that if I left my job, everything would turn out terribly. But that’s a lie. So a game I like to play is to imagine the worst-case scenarios of a decision. If I quit my job, what would happen? Would I be homeless? No, I own my apartment. Would I starve? No, I have savings. Would I not be able to afford nice things? Well, yes, but is a flashy car actually important to me? And what I realized is that the scenarios are usually not that bad. You just have to keep asking yourself “So what?’”.
Mark then started sharing examples of famous entrepreneurial figures from history who pursued their dreams and succeeded. Somewhat ironically, he interspersed his examples with personal stories about how unhappy he used to feel when he would compare himself to his coworkers. Mark shared for 10 minutes before another attendee was finally able to cut in.
I don’t share this story to criticize Mark’s verboseness. I’m sharing because Mark finally made me understand what it means when someone says, “I want to share my story.”
I used to think that only highly successful individuals or people had the right to talk about their experiences and give advice. A reader once gave me feedback that they wished I shared my personal experiences more in my articles. At the time I thought the reader was being silly. Why would I share my story? I haven’t done anything remarkable.
But these meetups proved to me that I was wrong. It’s in our human nature to want to share our story. It’s not to make ourselves feel important, but because we want what we’ve been through to mean something. We don’t need to be extraordinary people to have gone through extraordinary experiences.
The people who came to the meetup hailed from different ethnicities, genders, sexualities, and socioeconomic classes. So I heard a lot of different stories. But after each story, individuals would consistently pull out the wisdom they gained and relate it to how they live today.
Like Michael, an older man in his 60s who used to be highly involved in the art world and had interacted with people from all different walks of life. His prior experiences taught him to never judge someone based-off how they look, but only by who they are as a human.
Or Kevin, a young adult in his 30s who happened to be neurodivergent. Due to his differences, Kevin had struggled to hold down a job in the past, even leading to times of homelessness. When the advice of being “true to yourself” came up from another attendee, Kevin was passionate to add how that was easier said than done.
Or Emily, a middle-aged woman who recently returned to New York to raise her niece. Hailing from a large family with multiple brothers and sisters, Emily always had a relevant anecdote or piece of advice to share regardless of the topic.
As humans, we live off stories. It’s how our brain works. The fact that the universe is absurdly random is a fact we ignore in our day-to-day lives. We prefer to live in a world of cause and effect where good deeds are rewarded, bad deeds get punished, and our experiences mean something.
So by sharing our stories, we are not only entertaining our audience but also making sense of our own world. We are arranging our lives in a logical progression to explain how we arrived to where we are today. The story we tell others is as much for their sake as for ours.
Closing Thoughts
Even as I write this article, I question whether I am actually trying to pass on knowledge or whether I am just trying to make sense of a bunch of disparate experiences. The jury is still out.
Regardless, while I am not sure I will host this meetup forever, I am extremely grateful for the experiences I have had, the stories I have heard, and the people I have met. If you’re curious to learn more about the logistics, feel free to email me at latenightfroyo@gmail.com!
NOTE: Each story shared is based-off a true conversation from one of the meetups hosted in the past year. However, to protect the identities of the attendees, I changed the names, ages, and genders of the people in this article. In some cases I also slightly adjusted or combined stories as well.