Leadership with heart, mind, and soul

Melons or Berries? and 25 Other First Date Questions

Added on by Sam Davidson.

Getting to know someone can be hard, awkward, and even boring. First dates, orientations, staff retreats - they all usually include some version of icebreakers or get-to-know-you questions that are tired. The "What's your favorite color?" train has left the station. So, in an effort to get to know someone better, whether you're sharing your first latte or embarking on saving the world together, here are 26 questions you can ask that should spark a story.

And when you're getting to know someone, you need a story, not an answer. Stories let us shine; they showcase a passion and give us context (not just content). You can tell what's important to someone when they tell a story - what they include, what they omit, when their eyes light up.

Here's to all of us telling better stories.

26 Great First Date Questions

  1. Do you prefer melons or berries when it comes to fruit?
  2. If you could be a background character on any TV show, which would you choose?
  3. Who do you admire that I've never heard of?
  4. If your plans for Friday night were suddenly canceled, how would you spend those hours?
  5. Would you rather shop for the ingredients or bake the cake?
  6. What routine in your life - if skipped or missed - knocks you out of whack?
  7. If you had the means to live in two cities at once, which would they be?
  8. If you found $100 on the sidewalk tonight, how would you spend it?
  9. Who - in your opinion - has the perfect relationship?
  10. What do you think about when you don't think about anything?
  11. What song are you embarrassed to have on your iPod?
  12. How old were you when you got your first cell phone?
  13. Who do you call or write first when you need advice?
  14. Who is the oldest person you know?
  15. Who is the youngest person you know?
  16. Was your high school prom unforgettable or very forgettable?
  17. What's the hardest thing you've ever done?
  18. What did you dream about last night?
  19. If you're going to a potluck, do you make something or buy something?
  20. What is the best meal you've ever had?
  21. If your house was on fire, what one photograph do you grab on the way out?
  22. Why is your house on fire?
  23. If you're in a new city, do you wander or stick to the itinerary?
  24. Where - or who - is "home"?
  25. What is one thing you own that you would never sell?
  26. What do you wish I would have asked you?

Of course, some of these questions may still fall flat. But, you at least won't have to bore yourself with "Boxers or briefs?" and who knows? If the person across the table likes to bring deviled eggs to the cookout, then you can go ahead and plan your exit speech for why you have to get up early the next morning.

Got any to add?

What new, better, fun, and story-giving questions do you like to ask someone you meet?

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