24 Questions To Ask A Guy To Determine Compatibility In A Relationship

24 Questions To Ask A Guy To Determine Compatibility In A Relationship

4. What word would clients/coworkers use to describe you?

5. What word would someone who doesn’t really know you well use to describe you?

6. What word would people you’ve hurt in the past use to describe you?

7. What word would you use to embody what you’re best at?

8. What word would you use to embody what you’re worst at?

9. What word would you use to describe what you’re most proud of?

10. What one word describes what you most want to improve about yourself?

11. What word would you use to describe who you were in the past, and who you’ve evolved to in the present?

12. What is your favorite side of yourself? When did you discover that side?

When do you most thoroughly express that side? Why do you love that side the most?

13. If you don’t know something, do you prefer to move on, ask someone, look it up, make a decision as to what you assume/think it is?

14. The first word that comes to you… What’s the word you’d use to describe how you like to vacation?

15. Do you believe in intuition?

Do you believe that you are intuitive? Do you trust your intuition? Are there times in your past when you ignored your intuition and regret it?

16. The first word that comes to you… What’s the word you’d use to describe what you’re actively working on in yourself?

17. When you’re feeling weak or scared, do you:

  • Fight (get defensive and angry)
  • Freeze (shut down, get quiet)
  • Flee (end things, run away, hide)?


18. What makes you feel safest, physically, emotionally, financially?

19. What makes you feel most seen?

20. Do you believe in a higher power?

What is that power? How does that power affect and interact with your life?

21. Are you a texter? Or do you prefer in-person conversation, or are you a phone person?

22. What holidays are important for you to celebrate? How do you celebrate them?

23. If there was a fire/flood and you had five minutes to grab all you could in your home and everything else would be destroyed, what would you grab?

24. If you weren’t in your career, and money wasn’t an issue, what would your dream career be, and why?

When you start into the revealing conversations, believe what your partner says.

If someone says, “I have issues,” or “I’m crazy,” or “I’m not a good person,” ask what they mean. Make sure to ask in an interested, not interrogative way.

What you might say is “It’s interesting, you have said a couple of times that you have issues. I wonder what you mean by that? I think we all have our own issues. I know that I can be kind of rigid sometimes and even emotionally shut down if I am feeling unsafe, out of control, or without some structure. What about you? What issues do you feel like you have?”


In shaping your question in that way, what you’re doing is:

  • Showing that you’re actively listening
  • Repeating back to them what you heard them say
  • Reflecting and revealing yourself first in order to show that it’s safe to share areas that you find to be personal weaknesses
  • You ask the question again to circle back and open the conversation up to them.

Don’t be afraid to go into your own issues, too.

“When it comes time to settle down, find someone who wants an equal partner.” – Sheryl Sandberg


By answering their questions, you’ll show them you don’t believe you’re blameless or perfect. It proves you’re open to their questions and feelings, too. This will help create expectations and the foundation for equal and open communication.

In addition to the topics and conversations already addressed, here are more essential conversations to deepen and expand your relationships. Even answering these questions on your own and for yourself will be extremely illuminating, allowing you to get a clearer understanding of who you are and why you do, say, and act the way that you do.

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