365 Connecting Questions for Couples (Revised and Updated)

365 Connecting Questions for Couples (Revised and Updated)

It All Started With a Question.


“Hi, what’s your name?” a cute guy asked me at a coffee shop one random day twenty-three years ago. “I’m Casey.”

One question led to another, and we ended up chatting for a while that evening. There was instant chemistry. You know the feeling—butterflies in your stomach, heart all aflutter, can’t-takeyour-eyes-off-each-other kind of excitement. We both fell hard and started dating shortly after.

I still remember those dating years and how easy it was to spend hours lost in conversation. I wanted to know everything about Casey. Where he grew up, what his family was like, what his career aspirations were. I even wanted to know silly things like how he found out there was no Santa Claus. He could hardly give a wrong answer; I found each one fascinating. There’s nothing like that rush of early love when you’re eager to learn everything about someone you adore.

Less than two years later, we were married. Days turned into months turned into years, and things changed. Going into this, we were just about as unprepared as you can be to create a successful marriage. Between our sets of parents, there are twelve marriages, so we never had a model of what it takes for a relationship to last. We didn’t have good financial habits, either. Casey and I both hid purchases from each other and racked up over $250,000 worth of debt in just those first few years. Casey also had some traditional ideas of what kind of wife I’d be—cooking, cleaning, homemaking—because that was the kind of household he grew up in. But I don’t like to cook and always wanted to work outside of the home. Not to mention the fact that we’re both strong-willed, stubborn, and natural-born leaders, so there was hardly a topic we didn’t clash over. We fought over everything from our careers down to what was for dinner. Every. Single. Day.

We had zero conflict-resolution skills and both of us were dead set on trying to be right. Over time, we stopped going on dates. We stopped being curious about each other. Because almost every interaction led to a conflict, we hardly spoke at all. We didn’t ask each other about our childhoods anymore or know what the other’s goals were last month. And in the absence of meaningful connection, we grew apart. We were on the verge of divorce. There was so much hurt and distance that it seemed impossible to bring back the passion and romance we once had. Neither of us had any idea how to fix our relationship. We felt like two battle-worn combatants, exhausted from the war and helpless to do anything to get out of it. We didn’t want to fight anymore, but we couldn’t see our way back to each other.

One day, in the depths of the worst of it, I was sitting on my therapist’s couch alone because Casey wouldn’t go with me. I admitted I was thinking of leaving, and she let me rant for over an hour about everything that was wrong before she finally asked me, “Have you done anything and everything you can do to work on your marriage so you don’t live with regret?”

A good question.

The honest answer was no. I was mainly waiting for Casey to fall to his knees, beg me for forgiveness, and admit that it was all his fault. (That’d be nice, right? Not how it usually goes, unfortunately.)

“Well,” she continued, “creating a better marriage starts with creating a better you. You can’t control Casey or his actions, words, tone, or motivations. But you can control yours.” That sparked something in me. It forced me to evaluate myself and how I showed up as a partner. For the first time, I didn’t feel so helpless. I had agency. I decided right then to focus on what I could control so that no matter what happened to our marriage over the next year, I could be proud of who I was and how I handled it. I was dedicated to becoming the healthiest partner I could be.

My therapist began to walk me through a series of steps that focused on my own growth. The first of the steps was this . . .