25 Questions to Deepen Your Relationships

Whether you are enjoying a nice meal with a friend, talking with a relative, getting to know a new team, or looking to connect more with your romantic partner, this list of 25 questions will help you deepen the relationships you care most about in life.

The goal with all of these questions is that they should be conversation starters so your answer should be a story and not just a few word response. You should try to spend at least a couple minutes on each question, the longer and the more rabbit trails the better. Feel free as well to reword the question into your own way of saying it.

Let’s get started!

  1. What’s been your biggest highlight of the past year?

  2. Tell me about one of the most impactful places you’ve been to…

  3. Whose someone you’ve met that you would like to be closer with?

  4. What are you most excited for in the year ahead?

  5. What author would you like to get to have a one on one conversation with?

  6. Tell me about one of your fondest childhood memories…

  7. Who was your childhood best friend?

  8. Would you rather live downtown in a big city or in the rural forest and why?

  9. If you had to move to another country where would it be and why?

  10. Tell me about one of the biggest motivators in your life right now…

  11. How do you feel about your career/studies/business?

  12. What do you wish was different about our relationship?

  13. How can I be a better friend to you?

  14. Whose your best friend and why?

  15. Tell me about the neighborhood you live in…

  16. If you own pets, tell me everything about them… if you don’t own pets do you want to or not and why?

  17. What do you believe happens after death?

  18. Do you believe there’s life on other planets?

  19. What do you do for fun?

  20. Tell me everything about the last vacation you took…

  21. Were you raised in a faith system and do you still believe that way?

  22. Where is home for you?

  23. If you have kids, tell me everything about them… if you don’t, do you want to have kids?

  24. Are you happy with life?

  25. Other than money, what’s one thing in life that would bring you more life satisfaction?

Whether you are just around the corner of my office here in Cherry Creek Denver, Colorado looking for marriage counseling or from the other side of the globe looking for life coaching, I’d love to work with you.

I help individuals and couples from all walks of life obtain life giving relationships - from platonic to romance and from parenting to career, I can help you deepen the relationships in your life. You can read more about myself here and read more about my approach here.

The first step is to schedule a free consultation. Use the link below to get started. I can’t wait to meet you!

Schedule a Free Consult

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Redefining Masculinity: Breaking Down Toxic Gender Roles for Better Mental Health