Think You Know Your Date? Ask These Questions

We've all heard their stories: the couples who fall for each other and aim for the altar, imagining a future together that never ends—until one of them drops a bomb.

This is the woman who waits two years to tell the man she's dating that she's been married before and hasn't gotten an annulment yet. It's the man who'll never leave Florida but waits until his first anniversary to tell his girlfriend who lives in Michigan. It's the significant other who's drowning in debt, has three years left of probation, or plans to move to a different continent in a year and didn't think to mention it sooner.

Some bombs, by the way, might not actually be problems. But, boy, might they unveil a few. 

When you suddenly learn something about the person you're dating that would have been nice to know earlier, you notice the assumptions you've made about each other and how different your perspectives are. You see the conversation topics you have both been hesitant to approach.

And this is normal. When we wait to share or ask something, we often wait because it's prudent. You don't want to overshare or be vulnerable before being vulnerable feels safe. You don't want to scare your date away.

If the person you’re dating has a five-year plan, or a specific expectation of a future spouse, or the ball's already rolling on a major life change, you should know about it. At some point, withholding that information isn't prudence anymore—it’s manipulation. And that's why it feels like a bomb when we learn it too late.

But there's a way to learn it faster, and it involves asking and answering questions. You don't have to ask them all in one sitting (although nobody says you can't!). By asking as many of these questions as you can, you find out if you align where you need to. And you'll learn about your capacity to share, to have serious discussions, to negotiate, or to resolve conflict.

Some of these questions are fun. Others are serious. Still, others are downright awkward. But they will lead to good and important conversations. And remember that our list isn't exhaustive—there will always be more to ask.

About Past Relationships

These questions show you what your date has learned from past relationships and any maladaptive patterns he or she has (or hasn't) broken.

What complaints have other people you've dated made about you? Were they right?

What would your exes say you did well in your relationships with them?

What regrets do you have about past relationships?

Is there anything all your exes have in common—like something they fought about with you?

About Finances 

These questions show you how your date relates to money.

How much debt do you have (and what's your plan for paying it off)? 

What kinds of purchases are worth borrowing money for, and what kinds do you believe you should only make with cash? 

What are a few of the worst financial decisions you've made, and what are a few of the best?

Have you started saving for retirement?

When considering whether to purchase something, how do you determine whether you can afford it?

About Sex

These questions provide insight into how a person regards sexuality, into how familiar with chastity a person is, and into any sex-related addictions a person has.

Have you ever been exposed to pornography? Have you ever viewed it willingly?

Are you familiar with the Church's teaching on sexuality? If so, do you struggle with the teaching at all?

Have you ever been sexually active?

If your date hasn't been sexually active:

How do you define sex?

In what ways has chastity blessed you or been a difficulty in your past relationships?

If your date has been sexually active:

How many sexual partners have you had?

When was the last time you were sexually active? Why haven't you been sexually active since?

In what ways do you now pursue purity in your relationships or daily life?

About Lifestyle

These questions bring to light some expectations and plans you might not realize you each have.

Ideally, how many times a month would you like to make social plans?

What venues for socializing do you enjoy, and what venues for socializing do you avoid, and why? 

What would and wouldn't you like to have at your bachelor/bachelorette party?

Are you satisfied living where you live now, or is there somewhere else you hope or plan to live eventually? If so, where and how soon?

How do you expect your social life will change if you get married?

If you have kids, which option sounds ideal: to become a stay-at-home parent, for your spouse to stay home with the kids, or to have a two-income household? Are you open to the options that feel less than ideal to you?

Do you have a bucket list, and if so, what's most important to you on it?   

About Faith

These questions unveil the depth of your date's devotion, and whether he or she truly knows the Lord.

Are you a convert, or were you raised Catholic? If a convert, how did you decide to become Catholic?

When was the last time you went to Mass? How often do you go?

Are there any Church teachings that you disregard or don't understand? Which ones, and why?

What's your favorite way to pray?

What's the most powerful encounter with God you've had so far?

Has there ever been a period you spent away from the Church? How long did it last? When did you return? And what drew you back?

About Work

These questions may give you a feel for your date's work history, work ethic, and long-term career goals. 

Have you ever been rewarded for something at work? If so, what?

Have you ever been reprimanded for something at work? If so, what?

Have you ever been fired for cause? What reasons did your employer(s) cite?

How attached are you to your current job—are you happy and not looking, happy but open to new opportunities, unhappy but not looking, or unhappy and already applying for new roles?

Although some of these questions may be terrifying, remember that marriage is vulnerable by nature.

If you are pursuing your vocation together, it is important to learn how to share your feelings and opinions. Eventually, you'll see all of each other, even the parts you try to hide. So it's good practice while you date to divulge details, even the ones you're afraid to share, the ones that might be deal breakers.