The first time I had a conversation with the woman who would become my wife, I made her cry in a car on an hour-long drive in front of three other women, one of whom was one of her dearest friends. It could be misconstrued that I advocate making women weep to woo them, but allow me to clarify: I had no idea that I had made her cry.
She was driving the lot of us to see a movie, and I was sitting behind her in the night-darkened car. The conversation had been a genial one where people were asking one another about plans after school.
I had asked her what she wanted to “do” after college, and she had said she wanted to work in impoverished and war-torn countries as a relief worker and missionary.
I’d thought of how admirable this was as we drove up to the movie theatre, and as we got out of the car, my future-wife’s friend hopped out and pulled out a wheelchair and brought it to my future-wife’s door.
I was astounded. Her desires to help others fascinated me; I daresay I ignored much of the movie because I was thinking about this amazing woman sitting somewhere below me in the theatre.
After the flick, we got back into her car and this is where I made her cry.
I made her cry by asking her a question that mattered very deeply to her, a question that she had asked herself many times before, and had no answer for. I asked her, if she was willing to answer, how if she wanted to help those people she had mentioned, how would it function with her chair?
In retrospect, I am surprised that her friend did not use my own bluntness to bludgeon me to death, but I had to know this woman—she was the most incredible person I had ever known simply for the desires of her heart.
Caring Enough To Ask The Questions That Matter
To this day, her response astounds me. She said, “I don’t know. I don’t know how that would work. But I want to.” And when we got back to campus, she invited me into her apartment to introduce me to her friends over a cup of tea.
Months later she admitted to me that when we got into her apartment, the only thing she wanted to do was give me a hug. All she wanted to do was hold me and cry, not because I had hurt her, but rather because I—a complete stranger to her—cared. I cared about who she was. I cared about what she thought was important in life. I cared enough to ask her the questions that matter.
Dating can be hard, emotional, and confusing, but (in the words of my favorite lyricist), if you tell me where you’re going, I can tell you where you’re bound. If you think about your ends, it can help your beginnings. If you are intentional in your approach, it helps you be deliberate in your every action. I offer three suggestions in light of my experiences and insights.
1. Be Curious
When you begin dating, ask questions. Ask them of the person you are with, but ask them of yourself, too. Why are you on the date to begin with? Where can you see the good, the true, the beautiful in the other person? Remember this: you could know everything there is to know about physics and not know the person sitting next to you, and you would know less for not knowing them: people are the most incredible thing on the planet.
I encourage you to dive beneath the surface with a genuine care of what the other person's answers might hold. I often think back to a place where the question is written, “Who do you say that I am?” and I pose that question of my spouse and my Lord, remembering that the evidence for the answers come from without and merit my seeking.
This can be done in as simple a way as asking after their day or pursuing interests; don’t let your curiosity be limited to the surface level, but instead develop a genuine interest in the interior life of the person you are courting. If they say their day was fine, ask them for a “high-low.” If they loved the film, ask them why. If they are hurt or upset, rather than rushing to fix, ask them if they will tell you about the hurt. Curiosity, though it may come as a surprise, often is rewarded with understanding.
2. Be Honest and Trusting
This ought to speak for itself, but expressing what really matters is important. It is written that if you can be trusted in small matters, you will in turn be trusted with large matters. How true this is!
Expressing what is real, even in the most seemingly unessential things, is the foundation upon which you build your relationship with everyone you meet, so how much more necessary when you look to build a romantic relationship with someone! Be the person that your “significant other” can trust when they approach you with things.
After a few years of knowing my wife, we had shared all of the most embarrassing information we had to reveal about one another. My wife worded it in a way better than I ever could when she said, “I’m really glad that I can come and tell you things without being afraid of how you’ll react.”
She hit a truth there—when I told her about spending a little frivolously one month, she was able to take and trust, even though she wasn’t particularly pleased. When she got into a traffic accident, she didn’t try to keep it from me, but called me (knowing full well I would be unhappy, but trusting that I wouldn’t be angry with her).
And these small things either prepare or destabilize a relationship when it comes to matters of grave importance, that is, a life of marriage. It’s not a matter of cataloguing faults—indeed, far from it—but instead it is a matter of saying to someone as my now-wife said to me: regardless of the hardship, I trust you.
3. Will the Good of the Other
All things are directed to one end: perfect beauty, justice, truth and goodness. This is to say, all things are directed for God. Act upon this always. In all that you do, remember that your goal is Heaven.
The trick is that the other person's end is also Heaven, and you must realize that all things you do, for yourself and for them, must be directed for this goal. This will often mean sacrificing some pleasure, some desire to do a good for the other person.
Where there are a thousand ways you can do this, my advice is to start with the simple. C.S. Lewis echos St. Paul in his book, Til We Have Faces when he talks about love being able to die to oneself. Try it. Get up twenty minutes earlier so you can surprise him or her with breakfast. Take out his trash, wash her dishes, and clean the toilet; miserable tasks lose much misery when you are doing it for the joy of the person you love.



