Questions that dig deeper

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Last week, I was commissioned to put together some table topics for a church event to serve as a series of conversation starters. We go to a multigenerational church with more older members. Putting together some questions meant to help people dig deeper across generations was challenging, but I think I got a few good ones. If you’re ever in the need for something similar, or if you just want more questions in your repertoire for when you want to get to know people better, feel free to use the ones below!

I didn’t write all of these, just some! Others are curated from other sources, many of which I’ve forgotten over time.

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If you had to teach an introductory course about any topic of your choice, what would you teach?



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If you had to limit your phone to only four apps, which would you choose?



What is the most interesting question you’ve been asked during a job interview? (How did you answer?)



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When you think about it… do nachos count as salad? Why or why not? Make your case.


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What was your most memorable birthday?


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What soup is the best soup?

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What was the strangest movie that made you cry?

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Pick two:

Unlimited free food from anywhere at any time, y

our dog living as long as you, or u

nlimited free travel

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What was the last thing you did for the first time?


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You need to pay for a life saving surgery and your only hope is to win the money on a game show, which game show would you choose?

What is the most interesting fact about bugs that you know?

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What is the best advice about money you’ve ever gotten?

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Would you rather have three extra hours every day or one extra day every week?

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What holiday tradition is the worst?

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How has your birth order in your family impacted you?

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Share a great quote.

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What is a privilege you were born with that has benefited you?

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Have you ever saved a life or witnessed somebody saving a life? What happened?

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If your furniture came to life like in Beauty and the Beast, who would you hang with? Who would you be afraid of?


Do you have thick boundaries between your personal and professional life or are they more integrated? Why?

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What was the most unusual job you’ve ever worked?


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What did you decorate your walls with when you were 17 years old? (Did you even decorate your walls?)



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How do you stay informed with what’s happening around the world?



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If you could instantly teach yourself three languages, which three would you pick?


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How do you handle frustration?


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What is the most common misconception about you?

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What place-to-eat are you most excited to bring out-of-town visitors to?

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If you could master any skill that you have absolutely no experience in, what would you choose?

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What recharges you?

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What popular piece of technology do you have zero interest in actually owning?

What was the most memorable sporting event you’ve attended?

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Tell your life story in six words.

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They say that when a person’s body shuts down, hearing is the last sense to go. What do you want to be the last sound you hear?

How did your parents meet?

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If you could master one instrument and one language, what would you choose?

What word best summarizes your year?

If a mega-philanthropist gave you a large endowment to start a foundation dedicated to any cause, what would you fund?

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Who was the last new friend that you made?

My life will have been well-lived if: ______________________

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Of all the people you know, who has or has had the most bizarre job?

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If you could install a portal between your home and any other place in the world, what would you choose?



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If they made a musical about your life, who would you want to compose the songs?



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When you think about it… does cereal count as a soup? Why or why not? Make your case.


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You are a superstar and your agent advises you to endorse just one- product you use regularly. Which do you choose?



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What age do you feel like you are?

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It’s almost 2019. What piece of technology are you surprised still exists?

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What was your awareness or perception of your family’s finances as a child? How has that impacted you as an adult?

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Scariest animal encounter. Go.

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What is an unpopular opinion you have when it comes to music?

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If you were to have to completely switch careers, what would you want to try doing?

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New York, Los Angeles, Chicago, or San Francisco?

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What was something you ate as a kid that you thought was completely normal only to discover later in life that it wasn’t.

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Which round of trivia night is yours to dominate?

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What amazes you the most about your grandparents?

Would you prefer to have a housekeeper, a personal chef, a gardener, or a personal secretary?

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What other countries play a role in your family’s history? How connected are you to these places?

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What YouTube video always puts you in a good mood?

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If you had to wear the same thing every day like Steve Jobs, what would you wear?

How do use Facebook?

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If you were tasked with creating a documentary about any topic and given unlimited funding, what topic would you cover?

Philippe Lazaroblog18, blog