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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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69 Ideas for Better Married Sex

For many married couples, sex was once an amazing opportunity to express your love for one another. It was exciting, fun, and easy.  

But as time goes on, sex can become complicated, mundane, or even nonexistent.

We want to help you to enjoy sex for the gift it is — to be fully open, vulnerable, and connected with your spouse. This eBook will help you break out of your sexual ruts and reprioritize your sexual intimacy once again! 

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Our Members Report

emotional intimacy

Greater emotional intimacy


More passionate sex life

clearer communication

Clearer communication


Greater self-awareness