I Had Dinner With Six Complete Strangers. Here’s What Happened. 

By Gabby O’Keefe, Director of Communications, New York Press Association 

There are a lot of things I’d sign up for without giving them a second thought. A road trip? Absolutely. A weekend getaway? Count me in. Dinner with six complete strangers? That one made me contemplate a bit… 

A few weeks ago, I was doing what most of us do when we have a few minutes to spare, which is mindlessly doom-scrolling Instagram after a long day at work. That’s when I came across an interesting post from the Saratoga Dispatch promoting something called the Dinner Club. Since Saratoga Dispatch is one of our NYPA members, I was immediately intrigued. Part of me wanted to engage simply because I love supporting our members. The other part of me was just super curious. I’d never heard of anything like this initiative before, and if I’m being honest, I wasn’t entirely convinced people would actually sign up to have dinner with random strangers. 

What I didn’t realize was that the experience started before I even clicked “register.” I was never asked about a time or a restaurant that worked for me. I was just asked to fill out a questionnaire. I expected the basics: dietary restrictions, maybe whether I preferred indoor or outdoor seating, etc… There were questions like that, but it also asked things I definitely wasn’t expecting. How would you describe your personality? How do you usually approach conversations with people you’ve never met? What are you hoping to get out of the experience? Then came my favorite question of all: If you had to describe yourself using only one emoji, which one would you choose? 

I actually laughed. 

It felt less like I was registering for a group dinner and more like someone was trying to figure out who I’d naturally click with. I didn’t even think twice about my emoji choice at all. The second I saw the question, I knew I was picking the painting-my-nails emoji. It just felt very… me.  

Then, the day before the event, I got another email. Instead of introducing me to the people I’d be sitting with, it introduced me to a lineup of emojis: a martini glass, a smiling face, bacon, a laughing face, and a goofy face. That was it. No names. Just emojis. 

Naturally, my first thought was, Okay… who’s the bacon? Out of all the emojis someone could choose, bacon was definitely not one I was expecting. 

So I started making up stories in my head. Maybe the martini glass loved a good dirty martini and lived a very posh lifestyle. Maybe the laughing emoji was going to be the funniest person at the table. Maybe the bacon emoji… just really liked bacon? 

As it turns out, I was completely wrong. The martini glass ended up belonging to one of the sisters from New Zealand, who laughed and admitted she picked it simply because she enjoys a good cocktail every now and then. Her sister had actually been a last-minute addition to the dinner, so she never got the chance to choose an emoji at all. And the bacon? The bacon belonged to one of the women at my table who, without missing a beat, smiled and said she chose it because she was feeling “sizzlin’.” Iconic. 

The day of the Dinner Club, I received one final email with what table I would be sitting at, which was the Red Table, and what restaurant we would be having dinner at, which was the Coat Room, a hidden speakeasy tucked away just off Broadway in downtown Saratoga Springs. 

Going into the evening, my expectations were pretty low. I remember thinking, How many people are actually going to sign up for something like this? Well, turns out… a lot.  

When I arrived, there were a bunch of people seated on the second floor of the restaurant. There were people of all ages and backgrounds, and there was this quiet excitement in the room because nobody really knew what the night was going to look like. 

I found the Red Table. There were six people already seated, and I immediately noticed I was the youngest. Honestly, that didn’t surprise me, nor did I care at all. What surprised me was how welcoming and kind everyone was. Within ten minutes, we’d already skipped past the awkward small talk and dove deep into meaningful conversations. 

One woman had worked for the New York State Legislature in a department similar to where I worked before joining the NYPA, and we ended up realizing we knew several of the same people. Small world, right? 

Sitting directly next to me sat two sisters originally from New Zealand. One now lives in Saratoga, while the other was visiting with her son. Earlier that day, he had officially become a U.S. citizen, so naturally, without any thought or hesitation, the entire table raised a glass, and just like that, seven people who had only met thirty minutes earlier were celebrating such a huge life moment together. From that moment on, it didn’t feel like we were strangers anymore. 

By the time our food arrived, and yes, I’m still thinking about the incredible basil pesto pasta from that night because it was that good (shoutout to the Coat Room chef), it felt like I’d somehow known these people for years. Looking back, that questionnaire suddenly made perfect sense. None of us had been thrown together at random. The personalities around that table complemented each other so naturally. 

After dinner, all of the groups met up at Walt & Whitman Brewing which was a short walk down the street. The seven people at my table quickly became 50 people at a bar, sharing stories from their own dinners that very night. As I chatted with different people and got to know how they heard of the event, I quickly realized most of these people were loyal Saratoga Dispatch readers. They talked about the publication the way people talk about something that’s woven into the fabric of their community. That, to me, was beyond special. 

One conversation, though, has stuck with me ever since. I met a woman at the after party gathering named Amanda who had recently moved to the area with her husband. She told me she barely knew anyone and had signed up for the Dinner Club hoping to meet people. By the end of the night, she’d met dozens of new faces and already felt more connected to her new hometown than she had just a few hours earlier. I couldn’t stop thinking about that on my drive home. 

Working in communications, I spend a lot of my day looking at engagement metrics. And as much as those numbers matter, gatherings like this you just simply cannot measure. You can’t put a number on a new friendship or graph the feeling of finally meeting people in a town where you’ve just moved. 

As our industry continues asking how we can better engage our communities, maybe the answer isn’t always another newsletter or social media campaign. Maybe, every once in a while, it’s as simple as putting seven strangers around a table and trusting that good conversation will do the rest.