10 Questions to Ruin Your Dating Relationship (and 10 Better Ones to Ask)

Dating can be one of the scariest, most confusing, and most joyful times of life. You and your significant other are in a weird precarious space of enjoying each day together while also trying to discern your future, and it can be hard to find answers to all your questions. But I have learned that wisdom comes not in having all the answers, but in learning how to ask the right questions.

Dating my (now) fiancé was an absolute joy, and I learned a ton (by the way, he gave me permission to write this). One of the things I realized along the way was that there were some questions that had been engrained in me to subconsciously ask that are not actually helpful at all. Here are ten bad questions that I learned to reframe into better questions that helped me discern if we were a good match.

Bad Question #1: Is this person perfect?

“Duh,” you say. Of course that’s a stupid question. Nobody is perfect. But I think we (especially Christian leaders) can get stuck in this way of thinking far too often. 

Better Question: Does this person know the grace of God? 

Before I met my fiancé, I wrote in my journal a list of dreams for my future husband. One of them was “that he would have suffered and know the grace of God better because of it.” And one of the things I love most about my fiancé is not that he’s some perfect saint who never messes up but rather that he knows how to take me regularly back to the throne of grace, because he’s been there himself.

Bad Question #2: Is this person exactly like myself?

I’m not going to lie—I like myself a lot. My twenties were a time to explore my gifts and the ways I relate to God, and I have grown a healthy self-confidence. But being in a relationship has taught me that real partnership doesn’t mean we’re the same person.

In fact, real partnership is far better when the other person has hobbies, experiences, views, and ways of relating to God that are different than your own, because then you can challenge each other and not be blindsided by your own limited perspective. Think about a cross-cultural friendship you’re in: when you hit dissonance, if you choose to engage and not run away, the end result is always greater intimacy and joy. The same is true in dating. (Note: I’m not saying you shouldn’t be sure you have certain theologies and values that align. That is indeed important. But your partner doesn’t have to be your mirror image.) 

Better Question: Is my understanding of God and myself growing the more we date?

Bad Question #3: Is this person exactly like the rest of my community?

I have been surrounded by a lot of amazing people and leaders, and there are certain mentors and friends whom I consider “safe.” But looking to find safety in your significant other by wanting them to contain all the qualities of every single awesome person who’s ever come into your life can be dangerous. God gives community for a reason. It’s unfair and unhealthy to assume one person can maintain the role that the whole collective community should in your life. I have my fiancé, but I also have my counselors, girlfriends, and family.

Better Question: How does the role that this person plays in my life, together with the rest of my community, beautifully reflect the image of God?

Bad Question #4: Do we have fun all the time?

When you first start going on dates, every moment can be thrilling and exhilarating. But life isn’t really like that. My dad used to tell me, “It’s good to feel down sometimes. Our bodies need that to unwind.”

Better Question: Can we do boring life stuff well together? Like washing the dishes or sitting in silence?

Bad Question #5: Can this person love me well?

While this is an important question, I think in our culture we overemphasize what others can do for us. Real love is about laying our life down for the other. In the long run, your love will be sustained not because of what the other person can do for you, but because of how you let God make you more and more into a selfless person.

Better Question: Can I love this person well (even when I’m grumpy or irritable or when they’re not doing everything perfectly)?

Tim Keller has a lot of great insights on this.

Bad Question #6: Am I at peace every time I think about our future?

Others have often said to me that having a lot of peace about a decision is a good sign that you’re doing the right thing. But in my experience, that peace has never come for me fully until long after the decision has been made. William Bridges, in his book Transitions, talks about how even when really great things happen in life (marriage, new job, etc.), the real joy doesn’t come until you go through a process of death from your old season of life and a journey of disorientation as you embrace the new beginning. So a little fear and anxiety is not a sign you’re in the wrong place—just perhaps a sign that you’re still in process.

Better Question: Where in the transition process am I at currently? What deaths do I still need to grieve and what beginnings do I need to embrace?

Bad Question #7: Do we agree on everything?

Another “duh” question. Of course you won’t agree on everything! But when you’re in the middle of realizing that you may not see exactly eye-to-eye on everything, it can feel scary. As I mentioned before, however, a good partner is not your own mirror image. 

Better Question: Can we disagree well? Can we lovingly challenge each other into new ways of thinking?

Bad Question #8: Does this person lead the same way I do?

I think this question is particularly challenging for strong female leaders. We are often told not to settle until we can find a partner who “can lead us.” But we can be tempted to translate that to mean, I must find someone with all of my exact same strengths and then some. That’s never going to happen. Leadership comes in a lot of different forms. God has given me certain leadership gifts and he’s given my fiancé certain leadership gifts. Rather than comparing ourselves to each other and stuffing ourselves into the gender role box that culture has set up for us, we have instead looked at our unique strengths and challenged and encouraged each other through them. 

Better Question: Do we make each other better leaders?

Bad Question #9: What if there’s someone better?

I hear this fear arising more and more in our “swipe right” culture where there is always someone better “out there.” Underneath this question is a fear that we will miss out on the best life. But really, the best life is found in following Jesus, not in making sure we’re setting up the perfect future for ourselves. Now, don’t get me wrong—there is wisdom in not settling for the first person who says we’re attractive, but learning to commit to someone can actually bring far more peace than continually wondering if there’s somehow a perfect future spouse waiting for us elsewhere. 

Better Question: Am I living the best life I can by following Jesus in what I know today?

Bad Question #10: Will we “live happily ever after”?

One of the scariest parts of dating is not knowing what the future will hold. And so we look to marriage as some guarantee that then our happiness will be permanent. Or we get stuck in anxiety, wondering if we are making the right decisions to secure our joy forever. But even if you end up marrying your “prince” or “princess,” he or she will never be your guarantee for happiness. Real joy and security only come from God.

Better Question: How can I experience the eternal promise of joy from Jesus today and now, and trust that he holds my future in his hands?