dating resource: 101 Questions to Ask Before You Get Engaged


I know, I know. Are they walking on a cold, rocky beach, or is that mulch? What is that weird, faint writing in the sky? Why is her face blurry? Why is she missing a hand? Stay with me. This cover doesn’t do the book justice. We really enjoyed 101 Questions to Ask Before You Get Engaged.

Though the book is written from a Christian faith-based perspective, many of the questions are not super specific to this. There’s also a section for those who have married before, which I appreciate. Not all single people are in their early 20s having never been married, ya know?

We took our little book with us all over. We tried to go through it in order, not skipping the questions we deemed as boring or too hard. We talked through questions at the park, in the car, and on dates. I love a good question, and Dan either loves it, too, or kindly puts up with it.

I recognize that this seems cheesy and contrived.

Looking back, though, we talked through a lot of topics that allowed us to quickly get to know whether or not this was a you’re-really-fun or you’re-the-one-I-want-to-marry thing. When it came time for premarital counseling, we had already figured out some of the things that would be especially easy or especially hard. Dan would say that it gave him a more structured way to get to know the things about me that mattered a bit more than liking film photography and Conan O’Brien.

Some questions from the book:
+ If I messed up a decision, how would you convey your frustration?
+ What is the greatest fear or concern you have about being married?
+ Describe your spiritual journey over the past ten years. What were the high points and low points?
+ To what extent do you see the way we communicate as similar and in what ways is it different?

You can buy this on Amazon new + used. It’s also in at least one Barnes & Noble near us, so it might be near you. Enjoy!

Did you use this book or a similar group of questions when dating? If you’re not quite there yet, do you see yourself doing something like this?


Read other posts in this series.

  • Kayla

    Ah, I love asking questions! Ha, when we came to visit you guys I printed off a list of questions to ask David in the car…
    Do you think these are questions that would be valuable when you’re already married? Or not so much?

    P.S. – it makes me happy that you’re blogging lots these days 🙂

    • natalie

      Kayla, I think you could use them! you might just have to rephrase some of them to be more applicable to marriage. to be safe and not waste your money, maybe you could buy a used copy of the book?

  • kaileyrogers

    I’m going through this book with my boyfriend right now and it’s great! It’s such a wide range of questions and great conversation topics!

    • natalie

      yay! glad you’re enjoying it.

    • Marilyn

      How are you guys doing now?

  • Shared this as a resource for my classmates that might be in therapy with newlyweds/engaged couples/etc. Thanks so much!

  • Okay, I had this book and thought the same things about the cover! Like, what happened there?!

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