06/23/2016 12:10 EDT | Updated 06/23/2016 12:59 EDT

How To Host A Dinner Party For Complete Strangers

Today, we live in jam-packed cities, yet ironically they can feel far more isolating than smaller, rural communities. I always ask people if they know the other people on their floor in their condo building, and generally their answer is: "not really." Everyone has to eat, so why not eat together?

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Young people sitting in a bright café are having a toast with glasses of white wine during dinner. The glasses are seen from bird's eye view while there is food and flowers on the table.

Before the how... Why?

A few years ago I was in New York for an entrepreneurship boot camp and noticed an interesting trend. A lot of the successful people that came to speak with us frequently referenced how they met each other at group dinners. When I got back to Toronto and was working on building a business, I started to bring the various smart people I knew together for dinners to keep in touch and connect them with one another. Over time, I found that a lot of great connections and ideas would come out of these dinners.

Eating together involves sharing food, sharing ideas and connecting with other people. It's something we've been doing as long as humans have been on this planet. Today, we live in jam-packed cities, yet ironically they can feel far more isolating than smaller, rural communities. I always ask people if they know the other people on their floor in their condo building, and generally their answer is: "not really." Everyone has to eat, so why not eat together?

I started RNDMDNR to solve my own problem. I wanted to be able to meet people with different backgrounds and ideas about the world over a meal.

What I've learned from bringing people together is that hosting requires a bit of finesse. I put this guide together for people in our community who wanted to host a RMDNDR themselves. I hope it inspires you to meet more people over meals whether you become a part of the RNDMDNR community or just start inviting people you know to eat with you more often.

Two Things to Keep in Mind as Host

1. How, What, Why, Who, Where, When?

The three-question rule is simple. When you are engaging in a conversation with someone, when they stop telling you about something ask one more small, one-word question. These questions aren't intrusive and are open ended. Asking these questions does two things:

People are icebergs  -  they keep 90 per cent of the story bellow the surface.

Asking a few extra questions for additional clarification or context can help get people to share things you wouldn't expect. Further inquiry is especially valuable with people who might be a bit shyer or introverted.

People need encouragement  - coach and coax conversation

Head nods and small statements like "I see" or "interesting" help to encourage people to keep opening up. Asking short additional questions that are inquisitive helps people develop the impression that they should share more. In other words, these little questions make people feel safer to share by demonstrating that you care about what they have to say.

2. Everyone is Different

At first, you will want to make sure to engage everyone, but keep in mind that everyone is different. Some people are outspoken, and others enjoy listening. Just because someone is silent doesn't mean they aren't enjoying themselves. As a host, you may feel inclined to ask a lot more of someone who is less talkative than someone who won't shut up. Subtly asking someone who is a bit more quiet for their thoughts on something a more talkative person is rambling on about provides an organic and subtle chance to change the pace.

Three Stages of Every Random Dinner

Stage One  - The Warmup

Make sure everyone gets a chance to stretch

For the first 20 minutes, people will start arriving. Most won't arrive at the same time, so you will have to bridge the gap for people as they arrive. Personally, I find it hard to remember names -- not ideal for someone who hosts people regularly. Remembering stories, however, is much easier, which is why I have a slightly different strategy. I ask questions that give me context as to how I can introduce people without having to mention their name.

Although these questions aren't groundbreaking, they give you a bit of context to get started.


  • Where are you coming from?
  • What were you up to before you got here?

Usually, I follow that up with a secondary inquisition. If they were at work, "What do you do for a living?" Did they mention a neighbourhood? "What's there?" One extra level of inquiry, and possibly a third. Keep in mind the first rule of being a good host is to encourage guests and get below the surface.

When another person shows up, recap a short snippet of what you've learned about each person for the new person who joins the table. Then ask the new arrival a similar starting question. The snippet will show that you are paying attention to the guests that are already there. It also provides each new arrival with some concept of how to engage with others who are already sitting around the table.

Once everyone is around the table you can start to ask icebreakers. Some of my favourites include:

  • If you could study anything and money was no object, what would that be and why?
  • What is one thing you learned from something you've read recently?
  • Who is the best person you follow on social media that you don't know and why?
  • "What's your favourite pair of shoes and why?" is a recent one that a friend suggested
  • A master host I know tends to lead with "What are you most excited about?"

These are curve balls that are easy to hit. You'll notice that each of them is an open-ended question. "What is a great book you've read?" often results in Book Title, but asking them what they've learned gets them to open up and tell a story. Ultimately, these questions are easy to come up with as long as you ask questions that are hard to answer with one-word answers.

After the first 30 to 45 minutes of being mindful, leading the conversation and consciously engaging people, ideally, attendees will start to feel more comfortable speaking up or asking their own questions.

Stage 2 -  Middle of the Road

Cruise control still requires some attention

Midway through each dinner, you may feel like it is on cruise control. People are chatting liberally. At this stage, it's more about making sure everyone feels included in the conversation. Side conversations will start to happen which is not only fine, but a great sign that people are getting along.

If things are quiet, it is a good time to open up about yourself. Since you've spent the first bit of the dinner learning about everyone else, they are likely to be interested in hearing more about you at this stage. I find people ask me a lot of questions about Random Dinner in general; it's likely they will do the same with you  --  only say good things! (Joking! Well, not really.) Share past experiences and why you wanted to host a group of people. Discuss what you are excited and passionate about as a person. At this stage, as the host, you are letting the conversation drive itself, with the occasional course correction.

Stage 3 -  Wrapping Up

"I try to say goodbye, and I choke."

Each dinner has a natural flow of its own, and disrupting that flow is the hardest part. You'd think the most awkward part of the dinner would be at the beginning. It isn't. In the end, people question whether it's OK for them to leave, they question whether or not they're lingering. They question the protocol around heading home for the night.

Typically, what I've found works best is to suggest that you are up for hanging around a bit longer but if anyone needs to leave they should feel free. Do this within 15 minutes of the meal being over. This suggestion gives anyone who wants to get out of there the license to leave while encouraging people to hang around if they are enjoying themselves. Usually once someone leaves, people will make the decision as to whether or not they want to keep hanging out or not.

When people are having a great time but you need to get out of there, draw attention to how awesome it is that everyone wants to keep hanging out, encourage them to stay and tell them why you need to leave.

Want to experience a RNDMDNR for yourself? Sign up for our list at or join us for our first Massive RNDMDNR celebrating Chocolate Day on July 7 at

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