Interesting Conversations and Making a Connection

Some people are so good at “chitchat”; I am not. I prefer real conversations with meaning, controversy, humor, passion, or something you can take with you. I love it when you can really get people talking. I took a bunch of teenagers on vacation once with another mom. We had dinners every night, and each day they were on their own. At dinner, we posed different questions. It was fascinating to hear their answers; they shared experiences and insights, and it was really fun to listen. I can’t imagine having had five nights of chitchat. Over those five dinners, we got to know those kids so much better and built connections with them that have lasted for decades.

I love “connecting” with people I care about on trips or at an occasion as simple as a dinner party. If the guests don’t know each other, I always ask each to tell a little about themselves—and then I softly encourage a time limit.

I often use the “questions game” at dinner parties. I mix people up, meaning I sit people together who don’t know each other well. My friends come from many different places and from different lines of work, religions, and income brackets. They’ve experienced different traumas and tragedies and have different passions. They bring all this to the table when they engage in conversation. Almost any question works as a starter, but here is a short sample:

• Who do you love most in the world and why?
• If you could have any job anywhere, what would it be?
• What is the most embarrassing thing that ever happened to you?
• You get one “do-over.” What is it?
• Which of your parents influenced you the most and why?
• You are given three million dollars, and you have to give it away. What will you do?
• You can fix one major thing in this world. What will it be?
• You have a month’s sabbatical during which you will go and help a charity. What will it be and why?
• If there were one thing about you that you could change, what would it be?

Taking conversations beyond the surface level isn’t always easy. People feel comfortable at the surface, and moving deeper often entails a bit of risk. But the most rewarding relationships and conversations tend to happen when you move beyond the surface. You might just make a great new friend.