This Quick Tip Will Bring Any Boring Holiday Conversation to Life

My grandmother told me never to talk politics, religion or sex at the dinner table. While Grams might have just been uptight, there’s a better reason why: You get nowhere with it, and you learn nothing about another person. But do you just have to be bored this holiday season?

Renowned writer and speaker Fran Lebowitz says, “Great people talk about ideas, average people talk about things, and small people talk about wine.”

I travel for work, which means I’m oft-stranded in an airport bar or at a business dinner with people I’ve never met. The stakes are: It would be nice if these people liked me. But it’s not vital. I could pick a fight with them, just for entertainment, or I could have a nice conversation while talking to an expert witness.

Pretend you’re Sarah Koenig from the Serial podcast: You’re looking for an answer but are interested in the questions the search raises.

There’s something particularly sad about our current state where you walk into an airport bar and everyone’s on their smartphone. But when I want to be sociable with strangers I use what’s called “openers.” These are open-ended questions with no agenda. Job-interview type questions. Something without a yes/no answer. What they reveal about another person can be mundane or fascinating.

My favorite? “Pardon, if someone bought you a gift and they had to guess your size, is it better to go too big or too small?” My friends call it Cashmere Sweater, because the first time it came up we were discussing an unreturnable sweater on vacation.

Because the question is so harmless, you can see the little birthday candles in each person’s eyes as they remember gifts of days past. There is no answer to this question. It works well in groups. Great with couples (who file the resulting info under “Good to Know”).

The debate goes down something like this:
“Definitely too small. For a woman.”
“No. Too big. If she can’t fit into it she’ll feel bad.”
“No. If it’s too big she’ll think he thinks she’s fat.”
“Why doesn’t he know what size I am?”
“He should know what size you are. Wait. What if all your clothes don’t fit because you just lost weight and he gets you more stuff that doesn’t fit? That’s worse. Small. No. Big.”
“Two words: gift receipt.”
“I hate returning things, so get it big so that at least she can wear it at home if it’s baggy.  If she physically can’t fit into the thing, it’s like you didn’t get her anything at all.”

Some people want all the details. Are we talking something adjustable or intimate? The best way to say it is to act like you’re looking for a rule. Pretend you’re Sarah Koenig from the Serial podcast: You’re looking for an answer but are interested in the questions the search for that answer raises.

Older men tend to smile, remembering the time they got it wrong. Everyone—everyone—has a story. If asked, I say something about how my friend just had a baby and he wants to get his wife something that doesn’t feel like maternity clothes. If it’s in an evening environment of age-appropriate people, I like to tell the story of buying lingerie for a woman.

It’s great to ask two girls who are best friends. Or sisters. Cousins. No two people give the same answer when pressed.

I like open-ended questions because you end up learning something different about each person from their answer. Often it leads to another harmless talk. A chuckle story about something Dad did for Mom on Valentine’s day. There are others, but at this point, it’s likely I’m sticking with Cashmere Sweater. Give it a try and maybe you will, too.

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