60 Deep Questions to Ask (and Funny Ones to Break the Ice)

Good conversations rarely happen by accident. These questions work at dinner, on a road trip, on a first date, or with friends you have known for years. Start with a few funny ones, then go deeper.

Funny questions to warm up

  1. What is the most useless talent you have?
  2. If your pet could talk, what would it complain about first?
  3. What food would you ban forever if you could?
  4. What is the weirdest thing you believed as a kid?
  5. Which fictional character would be the worst roommate?
  6. If you were a ghost, who would you haunt and how?
  7. What is your most irrational fear?
  8. What would your autobiography be called?
  9. What is the worst haircut you have ever had?
  10. If you could only eat one sauce for the rest of your life, which one?
  11. What is a song you secretly know every word to?
  12. What is the strangest thing you have ever searched online?
  13. Which celebrity would you trust to babysit?
  14. What is the most embarrassing thing in your camera roll?
  15. If animals could vote, which one would win an election?
  16. What was your worst job ever?
  17. What is a hill you are willing to die on that nobody else cares about?
  18. If you had a warning label, what would it say?
  19. What is the silliest way you have ever hurt yourself?
  20. What would be your signature move as a wrestler?

More: funny questions to ask.

Deep questions to ask anyone

  1. What is something you believed five years ago that you no longer do?
  2. When do you feel most like yourself?
  3. What is a memory you return to when life gets hard?
  4. What are you still trying to prove, and to whom?
  5. What does a good life look like to you right now?
  6. Which relationship shaped you the most?
  7. What is a fear you have quietly outgrown?
  8. What do you wish people asked you about more often?
  9. What is the kindest thing a stranger has done for you?
  10. What would you do if you knew nobody would judge you?
  11. When did you last change your mind about something important?
  12. What is a small thing that makes you feel loved?
  13. What part of your childhood do you want to keep forever?
  14. What are you most grateful for this year?
  15. What do you think you are here to do?
  16. What is a hard truth you had to accept?
  17. Who do you want to become in the next ten years?
  18. What does home mean to you?
  19. What is something you have never told anyone in this room?
  20. How do you want to be remembered?

More: deep questions to ask.

For couples and first dates

  1. What made you say yes to this date?
  2. What is your idea of a perfect weekend together?
  3. How do you like to be comforted when you are upset?
  4. What is a tradition you would love to start?
  5. What did your parents get right about love?
  6. What is your love language, really?
  7. What is one thing you want us to try this year?
  8. When did you first feel at ease with me?
  9. What does trust look like to you?
  10. What is a dream you have not said out loud yet?
  11. How do you handle conflict, honestly?
  12. What makes you feel appreciated?
  13. What is your favorite memory of us so far?
  14. Where would you move if money did not matter?
  15. What are three things on your bucket list?
  16. What is a deal-breaker you learned the hard way?
  17. What small habit of mine do you secretly like?
  18. What scares you about commitment?
  19. What would our ideal home look like?
  20. What question do you wish I would ask you?

More lists: questions for couples, first date questions, and questions for friends.

Play them as a card game

Question Cards is a free conversation card game for iPhone and iPad with decks for couples, friends, first dates, deep talks, and funny moments. Swipe through cards, play together on two phones, and find the questions that get people talking. Download Question Cards: Couples Game on the App Store.

Made by Otter Media.