“So many great conversations never happen,” Professor John Cuddeback writes on his blog, Life Craft. “There is nothing like sharing insights with a friend into things that matter, and even things that don’t matter so much. But why is it so difficult?”
Conversation—true, deep, meaningful conversation—is one of the greatest gifts we can experience in our human interactions, and yet such conversations are not all that common. Increasingly, they are shoved to the margins of life by our addiction to technology, our overfilled schedules, and our growing cultural anxiety and isolation. Fewer and fewer people understand the art of conversation, an art so intimately tied to our very humanity. For what is more profoundly human than thinking together with others about important matters? As Aristotle says, humans are both rational and social animals. When you combine those two aspects of our nature, the natural result is conversation.
In the days before television and other forms of modern entertainment, the primary form of human recreation was talking: talking about the past, future, and present, sharing wisdom between generations. In his article “The Work of Local Culture,” Wendell Berry recalls, “There used to be a sort of institution in our part of the country known as ‘sitting till bedtime.’ After supper, when they weren’t too tired, neighbors would walk across the fields to visit each other. They popped corn, my friend said, and ate apples and talked.” That was the natural rhythm and flow of human life and the natural form of rest, relaxation, and true leisure. Entertainment, by definition, involved connection with others. But increasingly, that’s not the case anymore.
Plenty of people yearn for that deeper human connection fostered through true conversation, but often we are too shy or uncertain about how to get things started. One of the biggest hurdles to deep conversation is knowing how to begin. Once the ball of a good conversation is rolling, it often propels itself for hours through its own momentum.
To aid you in your conversational endeavors, then, here are 50 conversation-starting questions to help get you and your loved ones thinking about interesting, exciting, and meaningful things, while deepening your knowledge and love of each other.
Know Thyself (and Others)
- What is your most cherished childhood memory?
- What achievement(s) in your life are you most proud of and why?
- Describe a time when the idea of doing something terrified you, but you did it anyway. Why did you do it?
- What’s a skill you have that not many people know about?
- What’s something you’re nostalgic for?
- What is your personal motto?
- If you wrote a memoir, what would it be titled?
- Do you own any family heirlooms? If so, what’s the story behind it?
- Are you more like your father or your mother?
- How much do you know about your ancestors? Do you have any stories about them?
- What’s the best part about your day-to-day life?
- What’s something you’ve been waiting for for a long time?
- Who is the most influential person in your life?
- Describe an opinion you used to hold but no longer do. What changed your mind?
- What are you looking forward to most in your life right now?
- What’s the most beautiful thing you’ve ever seen? How do you define beauty?
- What do you do when things don’t turn out the way you planned?
- What celebrity do you most look up to (if any)?
- What traditions in your family do you want to pass on to future generations and why?
- Who’s the wisest person you know?
- Willa Cather wrote in her novel “O Pioneers!” that the only way to really help someone is to understand them. Do you think that’s true? What does it mean to truly understand someone?
- In Jane Austen’s novel “Emma,” one of the characters says, “There is one thing, Emma, which a man can always do if he chooses, and that is his duty; not by maneuvering and finessing, but by vigour and resolution.” Is it always possible to do your duty? How do we know what our duty is?
- Choose one of these topics to explore: “Socrates’ own conversation was ever of human matters. Investigating what is pious, what is impious; what is beautiful, what is ugly; what is just, what is unjust; what is prudence, what is madness; what is courage, what is cowardice; what is a state, what is a statesman; what is government and what is a governor—these and others like them, knowledge of which made a gentleman, in his opinion, while ignorance could fairly be called slavishness.” (Xenophon, Memorabilia)
- “Even when experts all agree, they may be mistaken” (Bertrand Russell). What’s something you think the experts are wrong about?
- Franklin D. Roosevelt famously said, “The only thing we have to fear is fear itself.” Do you think that’s true?
- In “The First Circle,” Aleksandr Solzhenitsyn wrote, “You only have power over people as long as you don’t take everything away from them. But when you’ve robbed a man of everything, he’s no longer in your power—he’s free again.” What does he mean by this?
- “We need never be ashamed of our tears” (Charles Dickens). When’s the last time you cried?
- In “Little Women,” Louisa May Alcott writes, “Be worthy of love and love will come.” Do you think she’s right about that?
- “Success is not final, failure is not fatal: It is the courage to continue that counts” (Winston Churchill). Describe a situation where you felt like giving up, but you persevered and eventually were victorious.
- What do you make of Shakespeare’s quotation from “As You Like It,” “All the world’s a stage, and all the men and women merely players”?
- Has a book or movie ever changed your life? What makes a book or movie life-changing?
- What does it mean to be successful in life?
- What makes a home?
- What is leisure?
- Describe the ideal vacation. As a follow-up, what’s the ulti
mate purpose of a vacation?How much does our ancestry shape who we are? Write down three words to describe yourself, then three words to describe the person next to you. Compare. What piece of music most touches your soul and why? As the old saying goes, “Familiarity breeds contempt.” How do we avoid this trap? If you’re married, when and how did you know you’d found “the one”? If you’re not married, how do you think you’ll know when you’ve found “the one”? What is the purpose of education? What does it mean to be a person of integrity? What’s one thing you would change about the world? What does it mean to die well? Just for Fun
- What was the best year the world has ever seen?
- Do you believe in ghosts? Why or why not?
- Do you know any good ghost stories?
- Do aliens exist?
- If you could live in any era of history, which one would you pick and why?
- Describe the best day of your life.
