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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?

  • 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.

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