Four ideas for sparking better dinner conversations

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A few years ago I attended a wedding as a guest and was excited to be seated at a table with a bunch of writers from the Daily Show. I anticipated it would be a funny and engaging group to chat away the next four courses with, but after some brief and awkward small talk—"So… how do you know the bride and groom?"—our attempts at carrying on a conversation amongst eight people ultimately felt too strained and tiresome and we all quickly settled into just talking to the people we came with. We were a diverse group of smart, interesting, creative people and yet that dinner felt like a painfully slow elevator ride where we were just trying not to make eye contact with each other in case someone tried to talk to us again.

A lot of thought goes into seating arrangements, a lot of negotiation and consideration of how to organize a vastly diverse group of relatives and friends, from different cultures, circles, and families, in a way that has some semblance of order or harmony. But in my experience, the thought process usually ends there. Many couples stick people at a table with a group they may or may not know, may or may not have anything in common with, and then leave them to their own devices, putting the responsibility on them to forge or deepen connections, fuel the conversation, and make a long meal engaging and fun. If the folks together at the table aren’t already acquainted, it’s quite like being at a dinner party with a bunch of strangers, and without a little support—and I don’t just mean the social lubricant of alcohol, though that certainly might help—it can be painfully uncomfortable for many people. How do you quickly orient people to each other to facilitate meaningful conversations?

I see the dinner portion of a wedding as an incredible opportunity to bring people together. The whole point of having a wedding is getting everyone you love together in celebration, but people need some guidance if they’re going to create a sense of unity amongst themselves. It’s unfair to leave the work of connecting the sole responsibility of your guests, so here are a few ideas for how to create an environment for connection.

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ASSIGN HOSTS

If this was a dinner party and not a wedding, the hosts would have the opportunity to introduce everyone to everyone else, but that’s largely impractical and impossible when the couple’s attentions will be fairly occupied. If you have multiple tables, consider each table as its own private little dinner party. There might be a compelling reason for the choice behind seating certain people together, but unless they are in on that reason, to the people at that table, it might feel a little arbitrary. A good dinner party has a great host or hostess. Consider assigning someone at each table to act as host, welcoming everyone to the table, making introductions, pouring wine, perhaps making a private toast to the table giving some insight into their relationship to you as a couple and why everyone was selected for this particular table, and asking some engaging questions to the group to get the conversation flowing. They can create a sense of camaraderie amongst their table, treating it as an exclusive club only those particular guests get to be a part of.

Some couples are hesitant to put any of their guests to work at their wedding and may resist the idea of handing out jobs, but for the people chosen for this role, it’s actually an honor to be singled out for their outgoing personalities and warmth. Obviously some thought would have to go into who would be the best people to host, and their willingness and openness would clearly factor into that choice. But everyone probably has a few friends and family members who are clearly perfect for and would relish this opportunity. Similar to inviting people to be in the wedding party, an invitation to play host at a table is a way of letting someone know they are trusted and appreciated. They don’t even have to publicize or announce their role. They can be just as successful in the role by just secretly being that super friendly person at the table that makes everyone else feel welcome and takes responsibility for the conversational flow.

CONVERSATION MENUS

Instead of having a menu of the courses to come on each plate, consider a printed conversation menu (like this, but designed to fit the wedding suite). The reality is, some people are just painfully uncomfortable starting up a conversation with a bunch of people they don’t know very well. Even the most extroverted folks often find it uncomfortable having to strike up conversations with strangers. A conversation menu is a great way to alleviate this anxiety for guests, and spark some truly engaging and meaningful discussion between them. Each course can include a topic or question to get them started.

The trick to a good conversation starter is that it gets people sharing personal stories rather than just opinions as storytelling connects us to one another more deeply. You can come up with some questions that are relevant to the guests or the wedding, but here are a few ideas to get started:

  • Describe a meaningful moment you’ve had in your life.

  • What does marriage mean to you?

  • What is something you’ve changed your mind about?

  • What did you learn about relationships from your parents? What have you tried to unlearn?

  • If you had to join another family, what type of family would it be?

  • What's the nicest thing anyone's ever done for you?

  • What small every day pleasure do you love?

  • What do you still want to discover in the world?

  • How would you like to be remembered?

If you need more ideas for great conversation starters, I highly recommend We’re Not Really Strangers. It’s a game of questions designed for connection, but the deck would be great inspiration, or just leave a stack of cards on the table!

15 TOASTS

The 15 Toasts model was created by the Art of Gathering author, Priya Parker. Tasked with getting a group of 15 people to converse from a place of vulnerability and authenticity in the context of a larger corporate event, she came up with the idea to invite everyone to give a toast on a specific topic. To keep things moving along, choose someone to start, and then each person picks the next person to give their toast. Parker has now been utilizing this approach for years and it has yielded incredibly real, honest moments of humanity and connection. An obvious choice for topic is to toast to marriage, but feel free to get creative or existential with it: to happiness, to romance, to beauty, to truth, or to the moment that changed my life. Choose a topic that feels personal and relevant to the couple, and then briefly explain the idea at the start of dinner.

INVITE GUESTS TO SHARE THEIR FAVORITE MEMORY

If you want to keep it simple, when the wedding couple thanks everyone for coming and welcomes them to start eating, they can invite their guests to share their favorite, most embarrassing, or most meaningful memory they have of each of them, or the two of them as a couple. Sharing personal, relevant, and meaningful stories is far more engaging than just sharing how they know them or why they are at their wedding. It has the added benefit of guests learning something new about the couple, and since only a few choice people are typically invited to give toasts to the whole room, it essentially gives everyone the opportunity to share what they mean to them.

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