3 Dares for Better Conversation this Holiday Season

How can we be so busy and still feel so lonely?

That’s a question on my mind this week as I finished my last work trip of the year, hosted and attended Christmas celebrations, and sent an endless volley of emails and texts trying to solidify plans for the coming weeks. 

In the midst of holiday festivities, we can feel like we’re communicating but not connecting because our conversations so often stay at the surface level. It’s small talk, not talk that matters. 

Remember the kids’ game “truth or dare”? Well, it’s true that many Americans are feeling lonely. (We’re in an epidemic of loneliness, according to the US Surgeon General.) So here are three dares—designed to help you strengthen relationships with the people that matter this holiday season. 

At your next family gathering or that final office holiday party, I dare you to do these three things:

  1. I dare you to ask a wide open question.

  2. I dare you to be the most interested person in the room

  3. I dare you to answer the question you want to be asked

Asking wide open questions

You know the difference between closed questions with a predictable, often one-word answer and open questions with less predictable, more subjective answers. This holiday, try for wide open questions. 

Here’s an illustration:

Closed: How’s work?

Open: What kind of projects do you like at work?

Wide open: How has work changed lately?

How’s work? is a mostly closed question, likely to get a predictable answer like “Busy” or “Good.” Asking a question about projects they love says, “I want to hear some details. Tell me what matters.” But it does contain the question to being about projects. A wider open question, like “How has work changed lately?” gives people a chance to respond about a project or anything else that is on their mind.

Be the most interested person in the room

You notice the word change there, right? I’m not suggesting you be the life of the party, the most interesting person in the room. (Remember that ad campaign? Instead, be the most interested. The most curious. 

Ask wide open question, then ask follow up questions. Make connections between ideas. 

In my experience, most people want to talk about themselves IF they feel safe and know the other person is genuinely curious. Research even shows that when on a first date, the other person is more likely to be interested in you if you ask more questions of them. 

The hardest part about being the most interested person in the room isn’t that you have to ask questions. It’s that you have to truly listen. 

Answer the question you want to be asked

You can’t always count on being asked a good question, but you can answer the way you want. 

“How are you?” is a bland question, but you can give a genuine, even vulnerable answer. Tell your friends about the great movie you just saw, tell your grandma about the new recipe you tried, and tell your colleague about a family holiday tradition you’re looking forward to.

When my brother died earlier this year, I desperately wanted people to ask me, “Tell me about Logan.” I wanted to talk about him. I did not want to answer, “How’s your family doing?” one more time. We weren’t doing great, but talking did help. So I learned, with friends who truly cared, to share the memories of Logan that had been on my mind when they asked how I was. 

What happened when I did? My friends listened with care. They were more than willing to hear my stories. It was less awkward than I thought, and truly helped me process my grief.  

Try it—what you want to talk about may be less serious, but it will still be significant if you are sharing something you care about. And your conversation partners are likely to respond in kind. 

I dare you to ask better questions, listen more actively, and share what is significant to you this holiday season.



Photo by Antenna on Unsplash

Previous
Previous

How to Develop Leaders: Stop Giving Answers, Ask More Questions