26 questions to spark great conversations

Whether it’s strangers at the table, family members at a reunion or new co-workers in the hallway, we all have people we struggle to make conversation with.

You can do better than talking about the weather. Or your jobs. Or whatever political, religious or social issue is hot these days.

You can come prepared to change things up.

Here are some thoughtful questions that could help you start beautiful, funny or heartfelt conversations.

All-time favorites:

• What song or singer do you always love listening to?
• What are your top three favorite movies of all time?
• If you could eat only one thing for the rest of your life, what would it be?
• What book would you recommend to your friends?
• If you had unlimited money and time, what would you want to do? Where would you go? Who would be there? How would you fill your days?
• What do you think the best age to be is? Why?

Family and friends:

• When/how did you know that your husband/wife was “the one”?
• How did you choose your children’s (or pets’) names?
• What’s something you admire about each person here?
• What’s the best advice your parents gave you? Did you listen to it?
• Who is someone that inspired you in your life? How so?

Life experiences:

• What moment in your life do you remember laughing the hardest?
• What’s something you’re really good at? What’s something you wish you were really good at?
• What’s something you did that was embarrassing at the time, but you now see the humor in?
• What was your favorite thing to do as a kid? (What did you save your allowance for? What did you race home after school to do? What did you write, talk and dream about?)
• What moment in history do you most vividly remember? (Where were you? What were you doing? How were you affected?)
• What are you most proud of in your life?

Lessons and advice:

• What’s the hardest lesson you’ve ever learned?
• What did you learn in your career that you wish you had known earlier?
• What’s your number one piece of life advice?
• What do you hope people remember about you?

Holidays and special events:

• What was your most memorable birthday? Why?
• What’s your favorite holiday memory?
• What’s the best gift you ever received?
• What’s the best vacation you’ve ever been on?
• What’s your favorite holiday tradition? How did it start? How has it changed over the years?

Listening to someone is an act of kindness.

Asking a person about their life, loves and thoughts can be a gift to you both.

Whether it’s a complete stranger or a family member you thought you already knew everything about, take some time to ask someone to share their story with you.

You’ll likely love hearing about it just as much as they love talking about it.

Want to show someone their story matters?
Our residents would be honored to talk to you.
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Additional resources: StoryCorps, TED, On Being, Humans of New York, Brain Pickings