Back in 2018, I wrote a piece for Fox News about a documentary called “The Dating Project.” Chris Donahue, one of the film’s producers, said the film was made in response to how difficult it is to date in America today.
“Relationships and marriage is probably one of the most important things you’re going to do in your life, right? But people don’t spend any time doing anything about it,” he says.
Amen. And that’s because young people are no longer groomed for marriage, which is essentially what dating is (or was): a necessary selection process for the purpose of making a wise choice in a mate.
With that process gone, single people are shooting blanks.
Most people think we marry a person on our wedding day, but in reality we’re marrying a life. How we feel about the person we marry does not determine its outcome. Being aligned on the kind of life both people want to live is what matters. Where are we both going, and how are we going to get there? Those details make up a life.
And yet, how two people feel about each other is the only framework young people have when it comes to looking for a spouse. As a result, they don’t treat the dating process as the interview it is. They don’t talk in advance about the kinds of things that will actually make or break their relationship.
Instead, they float along based on how they feel. Or they wind up married because hey, we’ve been together this long, might as well. Or because someone, usually the woman, is itching to have a baby. None of these is a reason to get married.
To have a successful marriage, the number-one skill people need is healthy communication about crucial topics that are relevant to everyday life. Money, for instance. That’s easily the biggest issue in every marriage.
Strong communication can absolutely begin before the wedding. To help people get started, I’ve compiled a list of questions to ask your person before you even think about marrying him or her.
Knowing the answers to these questions in advance will put an unmarried couple light years ahead of married couples who are struggling because they never addressed these matters at all. Many learned the hard way that they’ve never really been on the same page.
Using the list of questions below will help you avoid this fate.
What are your beliefs about marriage? Are they Biblically based (where a couple becomes one and works together as a team) or more modern in nature (where couples live more like roommates, keeping everything separate in the event of a divorce).
What’s the single most important thing you want to accomplish in life?
What do you/don’t you like about your parents’ marriage? What would you do differently?
What did you learn about money growing up?
How do you feel about debt?
Do you want children and, if so, how many? How will we raise them? Will they be in charge, or will we be in charge?
What are your views on work/family balance?
Did your mom stay home with you, or were you in daycare? How do you feel about all that?
What is your relationship with alcohol?
How important are health and fitness to you?
What will be the role of religion in our family?
Do you believe in divorce? Why or why not?
Are you open to getting help if we have unresolved conflict?
Do you embrace change or resist it?
What’s your philosophy about technology and the role it should play in our lives and in the lives of our children?
Do you have any addictions? What will you do if you develop one?
Do you like to socialize a lot or are you more of a homebody?
How important is travel to you?
Public or private school?
What role do you want your family of origin to play in our lives?
Are you a reader?
What are your politics?
Are you an early riser or a night owl?
How do you feel about pets?
Where do you want to live and why?
If this list feels daunting, keep in mind that many of the answers to these questions should become evident during the dating phase. I’m honestly always surprised to hear from married couple how often these topics did not come up. I mean, what are people doing with all that time they’re spending together? How do these conversations not happen spontaneously?
While you shouldn’t need to carry a checklist and a pen with you when you’re dating, if these topics don’t come up naturally it’s okay to be more formal about it. It’s okay to say to your person, Hey, I think we should sit down and make sure we cover some very important topics before we talk about marriage.
And here’s the best part. Even if you’re not far along enough in the relationship to say this, you can easily get answers to these questions in a less direct way. You don’t even have to ask a question at all, per se. Just cover one of the topics above by telling a story or by talking about yourself and/or your family of origin. That will prompt the other person to respond, and you’ll learn a lot about what they think that way.
At the very least, this will allow you to weed out the men and women with whom you know you could never marry. The faster you get answers, the faster you can move on. “Situationships” can then die, as they should.
To be clear, I’m not suggesting that by covering these questions you’ll have a conflict-free marriage. There is no such thing as a conflict-free marriage (unless you’re both conflict-avoidant, which is the greatest problem of all) because, again, you’re not just agreeing to marry a person.
You’re agreeing to do life together with that other person, and life is long. Neither person knows what’s going to come up or how the other person is going to respond to what comes up.
You can, however, minimize pain and ensure that you’ve made a solid investment. Might as well, since what we’re doing now with dating clearly isn’t working. I’m not even sure we can call it dating at all; it’s just very happenstance. Random. Disorganized. Messy. Chaotic.
The list above can change that.

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