Please ensure Javascript is enabled for purposes of website accessibility

Join us for our 2025 Couples Retreat

book-skinny-banner
Revised and Updated: 365 Connecting Questions for Couples

40 Date Night Questions

Forgo the dinner and a movie and go straight to really connecting with your spouse.

Love is not self-sustaining but requires constant maintenance. We can often get stuck on surface-y conversations but need to work hard at diving deep into heart level conversations. Don’t talk about your kids soccer schedules, your crazy boss, or your never ending to-do list. Instead, take these questions with you on your next date night and take turns answering them. Spend time listening to your spouse’s heart and soul.

  • What is your favorite memory as a child?

  • What’s my best physical feature?

  • If you could change one thing about your looks, what would it be?

  • What is your favorite memory of us dating?

  • Which of your parents are you most like?

  • What are your top 3 strengths?

  • What’s a new hobby you’d like to try?

  • How often do you prefer sex?

  • What was the first thing you thought of me?

  • If you won the lottery, what is the first thing you would do?

  • What do you like most that I do in bed?

  • How would you describe an ideal day?

  • What is something I can do to make us feel connected even more?

  •  

    Stop Scrolling!

    It's time for healing

    Marriage365 Membership is the #1 online resource trusted by over 100K couples to find, hope, healing, and connection. Let go of the pain for good.

  • What do you think we need to work on the most in our relationship?

  • What can I do to make sure you feel safe with me?

  • What’s the happiest you’ve ever felt?

  • What do you want to do when you retire?

  • For what in your life do you feel most grateful?

  • If you could meet one famous person, who would it be?

  • What’s another career that you think you’d love?

  • If you could go back in time, what age would you be?

  • Are you an optimist, pessimist or realist?

  • What was your favorite date night you’ve ever had with me?

  • What can I do that best says, “I love you.”?

  • In what areas are we the same?

  • Tell me a time when you felt really close to me?

  • How are we different?

  • Who do you know that has the best marriage? And what can we do to get there?

  • What’s your biggest regret in life?

  • If you bought a boat, what would you name it?

  • When did you first know you loved me?

  • How have I succeeded in our marriage this week?

  • What fears do you have?

  • What brings you the most joy?

  • How can I show you love this week?

  • If you gave money to charity, which one would you pick and why?

  • What turns you on?

  • If you could live anywhere in the world, where would it be?

  • What things do I do for you that refresh you the most?

  • What’s a question you’ve never asked me?


Written by 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.

Looking for more tools to improve your marriage?

Start your free trial 
and unlock hundreds of resources.

The #1 Marriage App

Congrats on taking the first step towards becoming a Marriage365 member!

Enter your email below to get started.

*By continuing, you agree to our Terms of Service and Privacy Policy

Get the Marriage365 App

Get the Marriage365 App