How To Have Better Conversations This Holiday Season

Nov 24, 2019

We’ve all been to that holiday gathering where there are a lot of humans in a room who have no idea what to say to each other but desperately want to connect.

Now, let’s be clear, I don’t recommend approaching your next family gathering or office holiday party as if you’re hosting a talk show. But as the host of Talk of Iowa it’s my job to ask people questions, and I do have some useful tips to share.

Small talk is small

When you haven’t seen someone for a while, it’s important to catch up, but most people don’t want to talk about their job on one of their few days off. Most kids don’t want to talk about school when they’re on a break. Your family members and friends who are struggling with illness or injury likely don’t want to detail their health problems on a day that is supposed to be fun.

How do you get to the good stuff? My best advice is to be more thoughtful with your questions. 

If you ask someone to “tell you what’s new,” they might get nervous and start rattling off a list of dates and names. They also might simply say “not much.” Then what?

If you haven’t done your research (to be transparent here, this is a euphemism for social media creeping), be creative. Think about things you could ask that will allow someone to tell a story.

What was their first job? Where did they go when you moved away from home for the first time? If they are married, how did they meet their spouse? What is something interesting they’ve read lately? If they could be any animal in the world, what would they be? What Thanksgiving dinner dish do they feel best represents their personality and why? You can also having fun assigning dishes to the rest of your relatives!

Older relatives 

When I was a teenager I realized that my grandparents were really interesting people. I wish I was better at asking questions back then, but I did have one super power on my side. I was a good listener, and I was interested in what they had to say.

Carl Nebbe is pictured on the far left in 1934 on the road with the Carl Nebbe Orchestra. He was the leader of the band and played tenor saxophone.
Credit Charity Nebbe / Special to IPR

Listening is the most important part of having a good conversation. Be engaged, pay attention and ask the follow up questions that come into your mind.

My Grandpa Nebbe lived a fascinating life. He was legally blind but still managed to become a professional musician. He played saxophone and clarinet and was the leader of a dance band that traveled the same circuit as Lawrence Welk. His stories were fascinating and he was good at telling them. The problem was that he didn’t think his stories were interesting, and it was hard to get him talking.

Ask you older relatives about their childhood memories. What kinds of games did they play when they played with their siblings in the snow? What was the worst blizzard they remember?

How did they cool off when it was hot outside in a world before air conditioning? What was the worst fight your grandpa ever had with his brother, and what was it about?

As weird as it might sound, asking about disasters sometimes make for the best stories. Holidays that go as planned tend to blend together in our memories. The holidays that almost didn’t happen are the ones that stand out, so ask about those.

Kids, tweens and teens

Kids are particularly good at shutting down the conversation with a brief answer. You want to talk to them, but they may not be too excited about talking to you. If you ask them yes or no questions, you’ll get a yes or no answer.

When I host a talk show, our producers and I do lots of research before we go on the air to do an interview. When it comes to the kids in your life, do your research. Find out what the kid, tween or teen you want to talk to is excited about. Are they into Minecraft? Fortnight? Band? Dinosaurs? Soccer?

Consider asking the teenager in your life to tell you what it means to “spill tea” or “ship” someone. You might gain a whole new vocabulary, but better yet you’ll have fun and get some insight into the life of a person you love.

Young adults and middle-aged family

Listening is the most important part of having a good conversation. Be engaged, pay attention and ask the follow up questions that come into your mind.

Family members aged 20-60ish can seem like the hardest age group to make conversation with if you don’t want to talk about work. And as I stated earlier, there are many more interesting things in anybody’s life that they would likely rather talk about than their job.

Parents love to talk about their kids, but if that’s boring for you, ask what they have been doing lately in their free time. Maybe they’ll surprise you by having a really unique and interesting hobby, or maybe you both love the same podcast or tv show.

Getting out a box of old family photos can lead to great conversations with people from all generations. Those of you who were on that family vacation to Yellowstone will have fun reminiscing and the stories might be fun for the family members who weren’t there.

If you do this, try not to get hung up on names and dates, just enjoy the memories. Pro-tip: If someone you love remembers something differently than you do, you probably don’t have to correct them or start an argument.

When I invite someone to be on Talk of Iowa they often come prepared with a story they want to share while we’re on the air. You can do that too! Think about a few stories from your own life that will get people laughing or reminiscing. When you give a little of yourself, people often respond by giving back.

Things NOT to do

While we’re talking about great tips for better conversations, let’s also talk a little bit about what I wouldn’t do.

Given the news right now, do not talk politics unless you absolutely, positively know what you’re getting into and it helps if everyone in the room is basically on the same page. Thanksgiving is not the day that you’re going to convince your dad to change his party affiliation. Needling your sister about supporting a candidate that you don’t like isn’t going to be fun for very long. Having respectful conversations about different beliefs can be an important and powerful experience, but the holiday dinner table might not be the right place for it.

Try not to be THAT relative. Your single 20 something or 30 something family member probably doesn’t want to discuss their dating life with you. If they want to talk about it, they’ll bring it up. DO NOT ASK.

The childless couple in your family may be not quite ready for kids, childless by choice or dealing with fertility challenges. DO NOT ASK. Are you curious? Of course you are! I’m curious too, but there are better, kinder and more discreet ways to satisfy your curiosity.

Are you the one on the receiving end of unwanted questions? Don’t let it ruin your day! If you are that single 20 or 30 something family member you know you’re going to get this question. Prepare yourself to deflect and change the subject with a fun question of your own.

And finally, always remember that this is Iowa, and we all love to talk about the weather.

Good luck and have some pie for me!