Gents, what is it about woman and their ability to craft the perfect question to get conversations started? If you are like me, I get stuck on asking the same questions. I’m here to help…

During my coaching sessions, I often refer to this list of questions for husbands to get the conversation started in the right direction. Trust me, you are going to score major points with this list. Our wives want to see that we show interest in who they are, their struggles, their dreams, their friends. But we can’t expect them to pour out their heart without our participation.

When asking these questions, listen with your eyes, turn off the TV, put your phone down, and rediscover the heart of your best friend!
  • What’s something you always wanted to do as a child but never got to do it?
  • If you could have one super power, what would it be?
  • What is one of your dreams that I can help you achieve?
  • What makes you feel overwhelmed?
  • Which would be the hardest to give up: coffee or chocolate?
  • What is your best memory of our dating years?
  • What could I do to make you feel more respected?
  • If you could bring one fictional character to life, who would it be and why?
  • How can I demonstrate my love for you in different ways?
  • What can I do to encourage and support you better?
  • If you could master one musical instrument, what would it be?
  • How do you like to be kissed?
  • What is one thing I can do to show you how much I love you?
  • What is one bad habit you need to break but you don’t want to?
  • If you could change your age forever, what age would you choose and why?
  • What did your parents teach you that you appreciate now?
  • What is your guilty pleasure?
  • Describe to me your ideal day?
  • What is your favorite movie of all time?
  • What are ways I can make you feel safe?
  • How can I show you that I am listening to you?
  • What achievement in my life would bring you great joy?
  • Who is someone that inspires you?
  • What was the moment when you laughed harder than you’ve ever laughed?
  • What can I do to make you feel more confident in our future?
  • What are some ways I can help you around the house?
  • How often would you like to go out on a date night?
  • What is your favorite thing about yourself?
  • What mutual goal would you like to see us accomplish?
  • What is something you would like us to do to invest in our marriage this year?

I want to see some husbands comment on this experience. Did your wife appreciate you showing interest? Did you learn something new about her? Was there a question I missed?

Casey Caston | Husband

PS: If you found this blog post helpful, check out Naked Conversations. It’s a great way to further connect with your spouse and take your marriage to the next level. Learn more and sign up for your FREE trial here!


Written by Casey Caston

Marriage365 Casey Caston


Casey Caston is the co-founder of Marriage365 and loves his wife, kids, and surfing – in that order. He’s passionate about teaching couples how to connect on a deeper level and works often with couples in crisis. He’s also officiated more than 600 weddings. His life long dream is to walk the Camino, surf in Indonesia, and publish a New York Times best seller.


10 thoughts

  • James

    Man, those are some amazing questions!!! We went through them quickly but I can see how they can help…we said were gonna go through them again when we have more time…thanks so much!! If you get any more good ones don’t hesitate to put them out there!!! Thanks again..

  • Jason

    I have been banking these questions. When we go out or
    Time to ourselves I would ask a different question. Some answers were interesting and some were surprising.

  • david

    I will try them with my wife. We need better communication. I am a horrible communicator and I have been slacking in a lot of these areas, but I have faith it will get better if I ask her and listen and write down the answers to these questions so I can take in the feedback. Thank you sooo much for sharing.

  • Tony

    My wife says I don’t listen to her and I agree it’s not one of my strong suits. I am going to sneak one of these questions in each day for a month and at the end present all questions and answers to her on our anniversary with my commitment to each and everyone.

Leave a Reply