25 Great Questions to Ask Your Loved One

Written by Kimberly Gleason on . Posted in Family

questionsThe food was sumptuous, the atmosphere eclectic, the music vibrant. The conversation? A bit dull. After dealing with kids and work all day, who wants to talk about kids and work? On a date night? There’s nothing that says romance like “Johnny threw up this morning.”

So I’ve come up with a list of twenty-five, thought-provoking questions to engage your loved one in intelligent conversation. Warning: Don’t ask these questions unless you honesty want the answers!

  1. What are three things I do that you really like?
  2. What are three things I do that drive you crazy?
  3. What have I done in the past that made you feel loved?
  4. When do you most feel loved and appreciated?
  5. What have I done that made you feel unappreciated?
  6. What is one thing that I can work on?
  7. What words would you like to hear from me more often?
  8. What would you like our marriage/relationship to look like 1 year from now? 5 years from now?
  9. What would you regret not having tried?
  10. Where do you feel like God is leading you? Us?
  11. What would you like to learn?
  12. What would you like prayer for?
  13. If you could travel anywhere, where would you go?
  14. If you could try something new, what would it be?
  15. If we could go on an adventure, what would we do?
  16. If we had $500 to spend on anyone, who would the recipient be, and how would we spend it?
  17. What points do you want emphasized in your eulogy?
  18. Knowing what you know now, what career would you have chosen?
  19. What are you hoping it’s not too late for?
  20. What do worry about most?
  21. What is the most beautiful thing you’ve ever seen?
  22. If you were stranded on a deserted island (with me), what five things would you want to have?
  23. What really makes you laugh?
  24. If you were to step outside your comfort zone in your spiritual life, what would you do?
  25. If God were telling you something personally meaningful right now, what would He say?


These questions will surely get you out of the boring marriage rut we all sometimes fall into. The trick, though, is to follow up your loved one’s answers with action. Scary? Perhaps. Exciting? Definitely.


Kimberly Gleason is a Grand Rapids-based personal and executive leadership coach, author, speaker, and trainer. She helps people and organizations to flourish, reach their potential, and achieve their personal, professional, and organizational goals. Her leadership development and coaching program, The Year of Leading Adventurously, begins in October. Check out her free e-books, blog, resources, presentations, and programs at www.kimberlygleasoncoaching.com.

Author Information
Kimberly Gleason
She is a professional, certified executive and leadership coach, business coach, career and life coach, trainer, speaker and presenter, facilitator, and published author of over 80 magazine and newspaper articles. Although Kimberly Gleason Coaching is a Grand Rapids, Michigan-based coaching company, I work nationally as well.

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