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The Best Question Someone Asked Me While Dating

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What questions do you ask yourself during or after a date?

I don’t remember who the date was with. But I clearly remember debriefing with my pastor’s wife afterward. No doubt I told her where we went for dinner and what we talked about. But then she turned to me and asked a question I wasn’t expecting.

“Did you have fun?”

Wait…what? Did I have fun?

When my pastor’s wife asked me that question, I dismissed it as silly. I didn’t need to have fun on dates. I needed to figure out if the guy I went out with was someone I wanted to marry — and the sooner, the better.

My life before college prepared me to be thoughtful about dating. I knew I shouldn’t rush into anything. I knew that dating wasn’t to be treated flippantly. I knew that the end goal of dating wasn’t sex or having someone to hang out with on Friday nights. I believed that dating was a tool God used to help me find my spouse.

So, I went into dates armed with a list of things I wanted to know about the person and experiences I wanted to do. I approached dating with a checklist mentality, ready to figure out what I needed to know so I could make an educated decision about whether or not to keep dating.

But there was a problem. I knew a lot about my dates’ theology, opinions and life goals, but I didn’t actually know them. I failed to account for the fact that dating was about cultivating a relationship with another unique image-bearer of God. I made the end goal of our time together to learn how (or if) they fit my ideal man stereotype without understanding their unique identity. I’d come to the end of a few dates realizing that although many of our views and ideals lined up on paper, our temperaments and dispositions didn’t complement one another or bring out the best in the other.

As I noticed this pattern, I began to consider my pastor’s wife’s question. What would it look like to have fun?

What do I mean by fun?

When I say “have fun,” I don’t mean going on or designing dates fit for a princess. Instead, the goal is to enjoy small, daily activities to enjoy one another’s company without the pressure of having deep conversations.

It could look like enjoying a TV show, making dinner, playing sports or a game, grabbing ice cream or a drink after work and just catching up about your day. I used to think this was time “wasted.” Activities like these felt frivolous, and if they could be avoided to get to meatier topics, that would be ideal.

But as I dated my husband and focused on “having fun” versus plodding through my checklist of things I needed to know in order to keep dating, I learned why prioritizing fun has value.

Why having fun matters

There are three reasons I think it’s valuable to have fun.

Having fun together can reveal someone’s character. 

What someone does for fun and/or finds funny tells you a lot about the person’s character. What does your date laugh at and find enjoyable? Some things you diverge on might just be different tastes (my husband loves Monty Python and I cannot stand them), but other differences might point to different values you share. Don’t go into a date hypercritical and ready to find and point out fault. But be aware of the differences if you see them.

Along with that, having fun with another person is an act of vulnerability. We all know the feeling of showing someone a YouTube video we think is hilarious, and then feeling uneasy when the other person doesn’t laugh.

Having fun together paces your relationship. 

When you simply have fun together, you naturally pace a relationship from going too deep too quickly. I’ve been on dates where we’ve talked about serious topics and shared pieces of our hearts right out of the gate, only to have one of us bow out, forcing us both to walk away bruised from having the relationship end so abruptly after personal conversations.

Conversely, when I’ve been in relationships that started with casual dates where we just enjoyed one another’s company, I was able to get a good feel for the person’s character without the emotional investment.

Additionally, shared experiences can build confidence in the other person and help you learn whether someone is trustworthy. When my husband and I dated, he would laugh or lovingly poke fun at my silly jokes, but never mock me. I learned that I could trust him not to demean my experiences when I shared more personal stories.

It provides insight into what marriage might look like.

Marriage is more than checking boxes off a list. Tim Keller describes marriage as a way that people “become their glorious future-selves through sacrificial service and spiritual friendship.” Friendship requires affection, kindness and camaraderie. When you have fun with another instead of constantly questioning if this person will be a good spouse, you have eyes to see whether or not you’re able to cultivate a life-giving friendship with the person.

Do you have fun?

Before I considered my pastor’s wife’s question, on dates I’d always think: “Can I see myself marrying this person? Is this the type of person I’d want to be my husband?” Instead, I started asking: “Is this someone whose company I enjoy? Do I look forward to spending time with this person?” These questions might seem obvious to you, but I was surprised at how often I dated people because we fit on paper but didn’t necessarily bring out the best in one another or find deep joy in the presence of one another.

Dating is certainly more than just “having fun” with a date. We need to have important conversations about our values, vision for life and what we think God is calling us to. We need to consider how God has created us and ensure that our potential spouses are wise choices in this regard.

But having fun isn’t a superficial activity. As my pastor’s wife reminded me through her question, “having fun” not only takes some of the pressure off of dating, it’s a way that God guides us as we seek to follow Him in our relationships.

Copyright 2017 Abigail Murrish. All rights reserved.

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About the Author

Abigail Murrish
Abigail Murrish

Abigail Murrish is a professional writer and amateur cook with a love for agriculture and gathering people around the table. Though she dreamed of a busy life in a big city while in college, she’s thankful for her quiet life in the Midwest where she spends most of her days writing and reading, drinking tea, walking her dog, putzing in her kitchen and sharing daily life with her husband, neighbors and church. Also, she likes to watch TV and is an avid fan of Parks and Recreation, the Great British Bake Off and Broadchurch. Find more of Abigail’s writing at

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