Fifty Great Date Ice Breaker Questions to Keep the Conversation Going

Updated on Sep 29, 2023

Sometimes it can be challenging to keep the conversation going on a date. Here’s a list of questions that can help.

I’ve been there. You’re on a date and the conversation goes quiet and you’re desperately trying to think of something to say.

So, I brainstormed and came up with fifty questions designed to spur interesting conversation on a date. There are tons of icebreaker questions available online, but these are specifically for dates. I’ve tried to steer clear of the first-date-taboo-topics of politics and religion, although the conversation could go there.

So, print these out and use them as your “cheat sheet” on your next date!

Fifty Date Ice Breaker Questions

  1. Describe something you’ve done that you’re really proud of. What is your greatest accomplishment?
  2. Describe a time when you experienced something that was almost too good to be true.
  3. Did you ever have a celebrity encounter? Describe what happened.
  4. You have to give an educational or inspirational TED talk five minutes from now. What topic would it be on?
  5. What was the best place you went for vacation?
  6. If you go could anywhere for a vacation, where would you go?
  7. Describe an argument you had with a previous boyfriend/girlfriend. Who was at fault? Who won?
  8. What are your pet peeves?
  9. What aspect of yourself are you currently trying to improve?
  10. What is the funnest thing you’ve done in the last week? Month? Year?
  11. What is the dumbest thing you’ve done in the last week? Month? Year?
  12. What do you do for exercise?
  13. Are you a city person or a country person?
  14. Describe your ideal dream home. Art Deco? Midcentury Modern? Craftsman? Spanish Style? Mediterranean?
  15. If you could go back in time to when you were a teenager, what advice would you give yourself?
  16. How is your relationship with your siblings?
  17. What is your favorite “guilty pleasure” movie?  (i.e., a movie that you know is awful but love watching anyway; mine is “Con Air”, haha.)
  18. What is the best movie you’ve seen recently?
  19. What was the best concert you’ve been to?
  20. What is your favorite city and why?
  21. Which is cleaner: your car or your bedroom?
  22. Do you like to cook? What is the best dish that you can make?
  23. What do people compliment you on most frequently?
  24. Describe the worst date you’ve been on.
  25. Describe the best date you’ve been on.
  1. What is the most embarrassing thing you’ve done on a date?
  2. How did you meet your best friend? Why do you get along so well with them?
  3. If you had to live in a different country, where would you live?
  4. Do you like roller coasters, bungee jumping, or skydiving?
  5. What were you like as a kid? Well-behaved? Class clown? Jock?
  6. What sports did you do in junior high or high school?
  7. What did you want to be (for your job) when you were in elementary school?
  8. Do you believe in ghosts? Have you ever seen or experienced a ghost or something unexplainable?
  9. Coffee, Tea, or neither?
  10. Beer, wine, or cocktail?
  11. If someone mistakenly deposited $200,000 into your bank account, would you report it if you knew it wouldn’t be caught otherwise?
  12. What would you do if you won 1 million dollars today?
  13. When was the last time you dressed up for Halloween and what did you go as? What was your best Halloween costume?
  14. What celebrities did you have a crush on when you were in high school? Now?
  15. What is the most adventurous or spontaneous thing you’ve done?
  16. What books are you reading now? Or, what is your favorite book?
  17. What was the last thing you made that most people would normally buy?
  18. What is your greatest natural talent or skill?
  19. Are you a morning person or a night person? What time do you go to bed and get up?
  20. What is one thing you would change about your body if you could?
  21. What is the best or worst job you’ve had?
  22. What would be your dream job?
  23. What was the best advice anyone ever gave you?
  24. Do you have any recurring dreams? Describe them.
  25. What are the best and worst parts of your personality?

Bonus Question

Which one of these words best describes you? Explorer, creator, teacher, healer, performer, defender, or something else?

Let me know how these work for you. If you have a favorite question not listed here, please let me know in the comments and I’ll add it! – Brian

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