35 Questions To Guarantee You'll Never Have A Boring Date Again

One thing I’ve learned from being a coach is that a truly great question can make magic happen.

Not only do I get to learn something awesome about someone else, but often as a result of me asking the question they realize a life-changing truth inside themselves.

Every person has a story.

Everyone has something that makes them unique, interesting, attractive, curious, mysterious, deep, or soulful.


If dating has slipped into the realm of “this is like pulling teeth” for you, then I encourage you to play a game by getting someone you meet to say “Wow, that was a great question!” during your date.


Because you’ll discover something awesome about every person you meet, and they’ll feel close to you in a way that exceeds the usual Tinder hook up.

I’ll give you 35 thought provoking questions that can make first dates a whole lot more fun and intriguing.

Here are some of my favorites:

  1. What should I know about you that I’d never think to ask about?
  2. What really makes you laugh?
  3. What is something you wish you did more of in your life and something you wish you did less of?
  4. If you won the lottery, what is the first thing you’d do with the money?
  5. What’s one fear you know is holding you back?
  6. What’s your favorite book of all time?
  7. What is a piece of advice that you were given that if you listened to it, you would not be where you are today?
  8. What’s your favorite place in the entire world?
  9. What’s something many people fear that doesn’t scare you at all?
  10. If you had to name one thing that really makes your day, what would it be?
  11. Who has been the biggest influence on your life?
  12. What is an accomplishment you are really proud of?
  13. What’s your favorite way to spend a weekend?
  14. What is one day you would love to relive?
  15. Is there anywhere else you would love to live?
  16. What do you hate most about dating?
  17. What’s on your bucket list?
  18. What are you most excited about in your life right now?
  19. What is the most thoughtful gift you’ve ever received?
  20. What’s your favorite thing about your job?
  21. What’s something that you sometimes outwardly wish more people realized about you?
  22. What’s something you’ve always wanted to try?
  23. If you could travel to any one country tomorrow, which would it be?
  24. How many times have you been in love and what did the experiences teach you?
  25. What’s one of your favorite childhood memories?
  26. Whats the stupidest thing you’ve ever done for love?
  27. Do you consider yourself spontaneous, or a planner?
  28. What’s something that comes easier to you than it does for most?
  29. What quality for you is an automatic “no way” when pursuing someone in a relationship?
  30. What was the worst job you’ve ever had?
  31. When you were a kid, what did you hope to do when you grew up?
  32. What is a piece of advice you often give but find yourself struggling to follow?
  33. If you could donate a million dollars to any charity, which charity would it be and why?
  34. What was the last thing you learned that made a big impact on you or an ah-ha moment?
  35. For what in your life do you feel most grateful?

I want to hear from you in the comments. What are some questions you’ve asked, or been asked, on a date that have really stirred communication?


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Photo Credit via @couples.goals.motivation

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