This Thanksgiving, get to know friends and family all over again with question games

Linda and Harvey Williams have a giant extended family, and a head count of 50 at their Thanksgiving meal wouldn’t be a surprising number.

That’s a lot of mouths.

But we’re not talking here about mouths to feed, we’re talking about mouths for talking.

Holidays are an opportunity for familial conversation that can head in several directions — all too often, south. This might be a good time to pull out a few tricks to promote fun and healthy conversations. No eye-rolling, teenagers.

“When I want to get a conversation started,” says Linda Williams, a grandmother, mother, sister, aunt, in-law, etc., “I bring out something I call ‘You tell me, I’ll tell you.’”

For example: Tell me something that scares you and I’ll tell you something that scares me.

“When we have time to keep it going, it typically leads into a whole bunch of conversations,” says Williams of Kansas City.

That’s important, says Laura Markham, clinical psychologist and parenting author, because the discussion among relatives during holiday times is not always, um, illuminating. Promoting healthy conversation can take a little planning, but not much.

“Otherwise you risk having the same old conversations you have with everyone every year,” Markham says.

Jennifer Schmidt, a popular blogger at and an advocate for enhancing family conversation, swears by the “conversation starter” game, short questions or prompts that can be pulled out of a jar to give direction to, and open up, good discussion.

Her family has been using the game for years, having stockpiled 240 questions. The questions can be fun and lighthearted or, when folks are more accustomed to the tradition, fairly deep, she says.

It’s a simple matter of picking a question, usually at random, and having one or more answer it. Or each person can pick his or her own question to answer.

Some eye-rolling? Maybe as an initial reaction, says Schmidt, whose five children are 11 to 20, but even teenagers come around.

“We’ve done it for parties, with teenagers around the table,” she says. “You might think they wouldn’t enjoy it, but they love it. Teens love to talk about themselves.”

Once, a visiting teenager, new to the game, positioned the conservation jar in front of him and pulled out question after question, answering each one, until finally Schmidt had to suggest he yield the floor to someone else.

“It was a testament to the fact that when you open up this theme of communication, people will want to participate,” she says.

The questions — which also can be story “prompts” — can produce anything from a good laugh to a personal insight to the unearthing of a lost story, and all of those things are a plus, Schmidt says.

Sometimes an answer will reference a deceased relative or an event that occurred before many in the room were born.

“My kids will say, ‘You never told us that!’” Schmidt says. “It can bring up stories that have been lost and allows for them to be passed to the next generation.”

If a conversation game is a new ritual, some people might feel awkward or uncomfortable, Markham says. The host should assess the crowd and try to keep folks from feeling put on the spot.

When the squirm factor feels high, allow choosers to skip a question they don’t like and pick another, she says.

At first, she says, use questions intended to be mostly entertaining: “If you got a tattoo, what and where would it be?” Or ones that can be answered in a light-hearted way, such as “What would your perfect day look like?” and “What do you find most inspiring in other people?”

Harvey Williams uses another strategy to launch conversations, particularly with younger relatives: He plays dumb, so to speak. To a grade-school student he’ll ask basic questions about a day at school, which gets the youngster to spell out what goes on there but then sparks personal tales.

“Immediately they’ll feel like, ‘Well, I’m dealing with someone who doesn’t know anything, so I guess I’ll have to explain it,’” he says.

Maril Crabtree of Mission plays another trick, which is mostly inside her head. She approaches someone she knows well almost as if she’s encountering that person for the first time, listening to them without all the memories, expectations, disappointments or irritations.

“Your mindset is, ‘That person looks interesting. I think I’ll find out about them,’” she says.

Markham understands the desire to broaden and sometimes deepen the conversations at big family gatherings. She has spent more than one long evening with relatives only to realize that she discovered almost nothing new about anyone.

On the flip side, Markham recalls going out on a limb and asking a somewhat distant relative about his childhood, a subject she had never broached with him. He was older and always seemed stern. She knew they were on opposite ends of the political spectrum.

“I was blown away,” she says. “I found out he had been taken in and raised by people who were not his parents. I had no idea he endured an ordeal like that. I saw this strength in him.”

Markham says we use stereotypes with strangers, or course, but we often do the same with co-workers and relatives, slotting folks as foodies, sports nuts, goofy elementary school kids, etc. Maybe this year is the time to break through, she says.

“Wouldn’t it be nice to know a little bit more about them as a person?”

No harm in trying the conversation game, Schmidt says.

“We are fighting for family time, and a lot of people don’t know where to start,” she says. “What I hope this does for families is to bring back a culture of conversation.”

To reach Edward M. Eveld, call 816-234-4442 or send email to Follow him on Twitter @eeveld.


Blogger Jennifer Schmidt and others offer these ways to fill a conversation jar with questions. Or, write your own. Just cut out or write on slips of paper or labels.

Several ways to play: The first player draws a question, answers it and asks the same question to another person. Then the jar passes to the next player. Or draw a question and have everyone answer it. Or have each player pull a question and answer it, in which case you might need more questions. Schmidt has a long, printable and free list at


▪ If you absolutely had to gain 10 pounds, what would you eat?

▪ When was the last time you laughed so hard tears came to your eyes?

▪ If you could live in any home from a TV series, what home would it be?

▪ What comes to mind when you hear “road trip?”

▪ If you could be an Olympic athlete, what would your sport be?


▪ Would you rather time travel 50 years into the past or 50 years into the future?

▪ When was the last time you cried?

▪ Are you a leader or follower? How do you know?

▪ If you had an extra hour every evening, what would you do with it?

▪ What’s the most courageous thing you’ve ever done?


▪ Which person in your family do you look like the most?

▪ What job do you never want to have?

▪ If you stayed up all night one night, what would you do?

▪ What’s the most trouble you’ve gotten into — so far?

▪ What’s the most important thing your parents have taught you?


▪ What do you do that you vowed you never would?

▪ What is the most beautiful place you have ever seen?

▪ What was your first or worst teenager job?

▪ If your life got stuck at one age, what age would it be?

▪ What’s something you should throw away but don’t?