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Inside a Deli Dinner: My First Experience

May 27, 2026
Inside a Deli Dinner: My First Experience

What really happens at a Deli dinner? One attendee, Ben from Chelsea, walks through his first night out with five strangers.

When we started The Deli, people kept asking the same question: what actually happens at one of these dinners? Do people show up awkwardly? Is it weird? Do strangers really become friends? Here is a write up from one of our attendees, Ben from Chelsea.

Before the dinner

Last week, I attended my first The Deli dinner. Two days before the dinner, I received an email with the details: the restaurant, the time, and the names of the five other guys attending with one sentence about each. I could see some of the interests we shared. I was asked to confirm I'd be attending and I did.

Arrival

I arrived at the restaurant right at 7pm. I went to the host and told her I was here for a dinner with The Deli, and she brought me to the table. There were two guys already at the table chatting about Iceland. We introduced ourselves and I jumped into the conversation and talked about my trip to Iceland back in 2023. Then another two guys showed up and the conversation morphed into talking about working remotely while traveling. By about 7:10pm, we all had arrived. Once we were all together, basic questions came up: where do you live, what do you do, how long have you been in the city. Nothing groundbreaking but fairly simple and chill.

Conversation flows

And then things started to click. The conversation shifted away from introductions and into real stories. One thing I liked about being in a group of six is that the pressure wasn't on any one person to carry the conversation. Someone always has another question, someone jumps in with a story, and someone reacts. The conversation starts moving naturally. I could chime in or just sit back and hear what others were saying. People started chatting about commonalities around work, fitness, sports, dating/being in a relationship. One guy talked about moving to New York during COVID. Another had just started a company. Someone else had moved from Brazil and was still figuring out the city.

And my favorite part was when the jokes started coming. One guy opened up about how a recent date went. Another shared a funny incident at work. The whole table relaxed. At some point, nobody was thinking about the fact that we had just met. It just felt like a normal dinner with friends.

What surprised me most was how quickly people opened up. There's something about sitting around a table with food that lowers everyone's guard. Instead of surface-level networking talk, the conversation became casual and relaxed.

Wrapping Up

The dinners are supposed to be 1.5 to 2 hours. Ours was a little over two. When the check came, the waiter split it up based on what people had ordered. That was nice and eliminated the awkwardness of figuring out who pays what. As we wrapped up phones came out and a group chat was started. We all then walked out together and said our goodbyes. I ended walking a few blocks with one other guy going in the same direction.

Overall, I had an enjoyable meal (Italian place) and great conversation with a new group of guys. The next day, the guy with the funny work story provided an update. I'm looking forward to the next dinner and adding The Deli to the rotation of events and things I do in the city.