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Fun First Date Questions

When I had my first phone date with my now boyfriend I was quite nervous. Not knowing whether there would be any awkward silences I went online and wrote down my favorite twelve questions out of the hundreds I had found. The amount of fun first date questions you can find online is incredible, if not a little overwhelming, so I’ve listed the best for you below for when you do meet that special someone.


  1. Do you have any brothers or sisters? Older or younger?
  2. Do you have a bucket list? What is / would be on it?
  3. Have you ever kept a new year’s resolution?
  4. What makes you happy?
  5. What’s the most spontaneous thing you’ve ever done?
  6. What’s the most embarrassing moment you’ve ever had?
  7. What’s your favorite movie?
  8. What’s your favorite music album?
  9. What do you like the most about where you grew up?
  10. Where would be your dream place to live if money was no object?
  11. What would you buy if you won the lottery?
  12. What would be your dream job?
  13. What is your greatest strength?
  14. What’s your proudest moment or greatest achievement in life so far?
  15. Which football team do you support and why?
  16. What three cities would you never ever move to – even for the job of your dreams?
  17. What is the best gift you’ve ever received?
  18. What is the most thoughtful gift you’ve ever given?
  19. Who has had the biggest influence on your life and why?
  20. Do you have any nicknames? How did they come about?
  21. What one piece of advice would you give to your eighteen year old self, knowing what you know now?
  22. What are your deal breakers in a relationship?
  23. If you could travel back in time where and when would you travel to and why?
  24. What do you think is the most important life lesson anyone could learn and why?
  25. What’s the best advice you’ve ever received?
  26. What’s your favorite book and why? Do you read much?
  27. Do you believe in aliens?


What do you think about the questions? Do you have some more of your own?  Are there any questions that don’t appeal? Please share your thoughts in the comments below to gain encouragement, insight and support from our community, we’d love to hear from you.

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