50 Thought-Provoking Questions to Ask for Better Conversations

Fifty conversation starters focused on ideas rather than your feelings—and how to keep the conversation going after the first question.

Look up thought-provoking questions and you'll mostly find questions about you: your biggest regret, your dream dinner guest, what the movie of your life would be called.

These questions are what I call "pseudo-deep": they sound deep and thought-provoking, but they don't really make you think.

The most interesting questions are those aimed at something bigger than yourself—at what's fair, what's true, what we owe each other, and where we're going and whether we even should. Nobody walks into the room with a finished answer to those. You work it out while you're talking, and so does everyone else at the table. That's what makes a conversation worth having.

So here are fifty truly thought-provoking questions, grouped by the kind of thinking they ask for: what if, what's real, what matters, and how we live together. (Looking for ethical questions based on what's right and wrong instead? Those have their own list.) After the list comes a short guide to asking them. Then one complete card, front and back, shows what happens after the first answer.

Who I am: I'm a former teacher & instructional coach—7 years specializing in classroom discussion and critical thinking strategies. I hold a B.A. in Philosophy. The notes on how to ask these come from a lot of hours watching what a room does in the minute after a good question, and after a bad one.

What makes a question thought-provoking?

A thought-provoking question is one you can't answer from memory. You have to work out what you think while you're saying it.

"What's your favorite book?" asks you to remember something. "If your memories could be perfectly recorded and replayed, would that make your life better or worse?" asks you to decide something you've never had to decide. The second one is harder and slower, and it's much more interesting to listen to.

A good question has three things going for it:

• You probably haven't answered it before. Not out loud, at least, and maybe not in your head either.
• It points past you. The subject is an idea, not your history or your feelings (even though your answer ends up saying a lot about you).
• The why is better than the what. "Yes" and "no" are both fine answers. The reason underneath is where the conversation is.

50 thought-provoking questions

Every question here comes from the THINK. deck. Eight are printed on the front of a card, word for word. The other forty-two come from the follow-up questions on the backs of cards. Some of those are reworded slightly so they make sense on their own. Use them at dinner, on a long drive, with old friends, or in a classroom. That's what they're for.

What if

Hypotheticals. Nobody's asking whether it could happen. The answer tells you what someone values.

1. If your memories could be perfectly recorded and replayed, would that make your life better or worse?
2. If you moved to another country, what would you actually do—adopt the customs or insist that yours be accepted?
3. Would you trust an AI to govern society if it could eliminate war, corruption, and waste?
4. If you found out your parents had edited your genes before you were born, how would that sit with you?
5. If a technology exists that could control the climate, should we use it?
6. If everything you did online were permanently tied to your real name, would you act any differently?
7. If you lost your job, your savings, and your housing in an economic collapse, what would you actually want the government to do?
8. If you personally had a profound religious experience, how much would it change your beliefs about reality?
9. If you had the chance to live on another planet, would you go?
10. If you were put in charge of helping a struggling community, what specifically would you do first?
11. If your home became uninhabitable because of decisions made by people in another country, what would you actually want from them?
12. If every country put its own interests above everything else, what would the world look like?
13. If you refused a treatment that would probably save your life, how would you want the people who love you to react?

What's real

What's true, what counts, and how you'd know.

14. If a digital copy of your consciousness exists, is it truly you or just a simulation?
15. What makes a religious experience count as evidence for God rather than just a personal feeling?
16. Is there a difference between being happy and being entertained?
17. What makes something a "right" rather than a privilege?
18. How would we know if an AI is truly conscious or just really good at imitating it?
19. Can things really be "owned" by a culture, and what does that look like in practice?
20. Have you ever been taught something in school that conflicted with your beliefs?
21. Is a drug that saves lives a product or a public good—and does that change who controls the price?
22. If your happiest moments happen online, does that make them any less real?
23. Is political speech a form of free speech, or should it be held to higher standards of truthfulness?
24. What makes land "sacred," and who gets to say?
25. Have you ever held a strong opinion about how people somewhere else should live—and what made you so sure?

What matters

What's worth wanting, keeping and protecting.

26. Is dying part of what makes us human, or just a problem we haven't solved yet?
27. How much does access to nature actually matter in a good life?
28. What should a society reward more: effort, skill, risk, or results?
29. Is marriage still important, or has society outgrown it?
30. Should humans keep trying to tame the natural world, or is there wisdom in leaving some things wild and unpredictable?
31. Is voting valuable because of what it does or because of what it represents?
32. Is progress defined by what a place becomes, or by what happens to the people who lived there?
33. Even if gene editing had no side effects and guaranteed results, why might some people still oppose it?
34. Is there anything from your own culture you'd feel strongly about if it was taken and used without context?
35. Is the goal of education to transfer knowledge, or is there something more to it?
36. What exactly about intelligence makes us feel like it's worth protecting?
37. What should matter more: helping workers, protecting businesses, or overall economic stability?

How we live together

Trust, rules, schools, and what a society has to share.

38. When is it okay for a group of people to break away and start their own country?
39. Are there any values that people must agree on for society to work properly?
40. Is some level of distrust in government healthy?
41. Should public schools be completely neutral towards culture or adapt to the communities they serve?
42. Should the size of a business affect what it's required to pay its workers?
43. If millions of people believe their votes don't matter and stay home, what happens then?
44. Should internet access for minors be regulated or would that be government overreach?
45. Does society lose anything important when religion declines?
46. Does living somewhere give you more of a right to decide what happens there, even if it's considered harmful by outsiders?
47. What would a government have to do for you to deeply trust it?
48. Do libraries have a duty to reflect community values, or do they serve deeper principles of intellectual freedom?
49. If unhealthy choices drive up costs for everyone, is that enough reason to regulate personal choices?
50. Do you think society as a whole would be better or worse if we knew whether or not God existed?

Where to start

Fifty is too many for one evening. You need one.

• Around a dinner table, go with questions 1, 16 or 27. Nobody needs any background, just an opinion and a reason for it.
• With a close friend or partner, choose questions 8, 26 or 39. You'll find out what they actually value.
• On a long drive, try questions 3, 12 or 14. They're big, they're open, and they don't need a quick answer.

After the first question

Many conversations with potential can fall apart after the first question. The other person says, "Yeah, I guess so." You respond, "Yeah, me too," and what could have been something interesting simply dies.

What's needed instead are good follow-up questions, which is exactly why THINK. provides three "Deep Dive" questions on every card. These are designed to push your thinking—to consider the specifics, the boundaries, the possibilities that the first question opens.

Here's question 1 exactly as it appears in the deck: the question on the front, the three follow-ups on the back.

If your memories could be perfectly recorded and replayed, would that make your life better or worse?

On the back

• Is there any specific memory you'd want to record—and any you'd want gone for good?
• Does forgetting serve a purpose?
• If you discovered that some of your most meaningful memories were untrue, how would that change you?

The first answer usually comes fast, and it's usually "better." Who wouldn't want their best day back?

Then the follow-ups go to work. The first makes it specific, and once you've picked the memory you'd keep, you've already thought of the one you wouldn't. The second asks whether forgetting is a flaw at all, or something we'd miss. The third pulls the floor out from under the whole question.

Three questions in and "better" usually isn't the answer anymore. That's the conversation doing its job.

Every card in the deck works this way. If you want to get better at asking follow-up questions, I broke down the pattern in 50 moral and ethical questions to ask.

Quick questions

What is a thought-provoking question?

It's a question you can't answer from memory. It doesn't ask you to recall a fact or a preference. It asks you to reason your way to a view, usually about something bigger than yourself. The best ones have more than one honest answer, and a reason underneath the answer that's worth hearing.

Is a thought-provoking question the same as an ethical question?

Not always. An ethical question asks what someone should do, or what makes something right or wrong. Plenty of thought-provoking questions do that, but most don't. They ask what's true, what matters, or what would happen if. This list leaves right-and-wrong questions out on purpose, because there's a separate list of moral and ethical questions for those.

Are thought-provoking questions the same as deep questions?

Not quite. People usually think of "deep questions" as meaning personal ones: your fears, your regrets, the thing you've never told anyone. There's a place for those, and plenty of card decks are built around them. But questions that are truly deep—that are thought-provoking and worth exploring—point outward at ideas: what's fair, what's true, what we owe each other. You learn a lot about someone either way. With these, you learn what they believe and how they got there. (I wrote more about that split between feelings, fun and ideas in this comparison of conversation card decks.)

What are good thought-provoking questions to ask friends?

Ask the ones where you genuinely can't predict what they'll say. From the list above, 2, 30 and 36 work with almost anyone. If your friends like something harder, try 15 or 18. People are often still talking about those on the way home.

Can you use these with teenagers or in a classroom?

Yes, and the tech questions are the easiest way in. Teenagers already live inside questions 6 and 22: who they'd be if everything they posted carried their name, and whether an online life counts as a real one. Start there, then move to 44 or 35 once people are talking. They'll have opinions about both. In a classroom, have everyone commit to an answer on paper before anyone speaks.

Where do these questions come from?

They come from THINK., a conversation card deck I made. It has 120 cards across eight categories, with one question on the front of each card and three follow-ups on the back: 480 questions in all. Eight of the fifty above are printed on the front of a card, word for word. The other forty-two are follow-ups from the backs of cards, lightly reworded where they needed it to read properly on a page. The card in the section above is complete, front and back, exactly as it ships.

If these are the questions you'd want to spend an evening on, that's what THINK. is: 120 cards, eight categories, one question on the front of each card and three follow-ups on the back. See the THINK. conversation card deck →