When You Know, You Know: Dating & the Mystery of Discernment

I remember the time when I began to think critically about dating. It was around eighth grade, and I had come across a blog on Facebook that offered Biblical advice on singleness, dating, sexuality, and marriage for women. Yes! I thought. Here it is, the wisdom I need to figure out how to do dating and purity *the right way*. They were always topics that were alluded to at church, yet I hadn’t had the time or resources to really understand them.

So I read. And I read and read and read. And prayed, and journaled in my loopy middle-school handwriting. I asked Jesus for a godly man. I asked Him to show me His will and to make me okay with lifelong singleness if that’s what I was destined for, although I sincerely hoped I wouldn’t end up alone. I made lists of the characteristics I would like in a future husband. I thought critically about those blog posts and other resources I came across, and by the middle of high school I had very clearly formed convictions about dating and purity.

I was going to save my first kiss for marriage. I was going to marry the first guy I dated because I was going to be intentional and wise and find someone with character because dating is for marriage, not for fun. I had a whole framework in my head for how to do it right. I thought, surely, with enough prayer and thought I could figure out before diving into a relationship if the person was right for me!

Oh, you little fifteen-year-old you. If only you knew anything of life and faith and the mysteriousness of love.

I still have those lists of “qualities in a future husband” saved deep in the labyrinthine archive of my laptop. Every now and then I pull them up for a good chuckle. What they say isn’t really that bad — I was mature enough to understand that character was more important than looks and mature faith was more necessary than similar preferences. But at that age I had no understanding of what it truly meant to trust God with these things, and the fierceness with which I clung to my convictions betrayed a grave overestimation of my own wisdom.

Fast forward four years — past two relationships, the thrills of infatuation, tears from breakups, even more books on dating and singleness read, and I’m sitting in a cafe with one of my mentors from my campus ministry.

“I feel like the more I do this dating thing, the less I actually understand how to do it the right way. It’s so confusing,” I bemoaned.

This confusion grew out of the fact that I was just a couple months past a breakup from a relationship with a guy who, on all accounts, had checked all the boxes on my lists. I couldn’t figure out why it didn’t work out, and this led to a lot of dissonance. For a long time after, I lived with a sense of discontentment and loss.

What I didn’t understand was that any relationship I thought should have worked was only judged right by my own human wisdom — wisdom which was (and is) fantastically limited. I thought that my lists and theoretical convictions were sufficient to evaluate whether a relationship was right, and I called this formulaic approach discernment. When that approach failed, I felt like God had failed me.

But of course God hadn’t failed me. My wisdom had failed me. In retrospect, I was encountering an issue of sight. I thought that I could see everything I needed to understand whom to date and how to date well. But of course I couldn’t see everything; only God can do that. It was as if I was looking through one eye with eyelids half-closed, wearing dusty sunglasses and yet still believing that I was seeing with 20/20 vision in every direction. This mistaken overestimation of sight led to too much faith in my human wisdom and not enough faith in the God who actually sees and knows everything.

Then, months later, I finally understood. It was such a simple revelation — one I could articulate and claimed to believe for a long while before — but it was such a game-changer for me, for my approach to dating, for my understanding of faith. For everything. I can’t see everything about my life or future or that of others, but God does. And He is always good, so His ways are absolutely best. Why wouldn’t I want to be led by the One who sees with crystal clear sight when I myself and am practically blind? Therefore, even though I may think I know what is right for myself, I must seek what God wants, even if His ways contradict my own. Even if what God wants is a breakup, or for me to choose not to pursue a relationship with a perfectly qualified guy on the horizon. Even if that means fully embracing my season of singleness despite desires to eventually get married.

No amount of lists or pre-planned convictions can amount to God’s omniscient wisdom. No amount of intentionality or listening to podcasts on dating or talking to other people can help you understand what God knows. There are plenty of posts in the blogosphere with titles like “7 qualities of a godly man,” or “Five ways to be intentional in dating.” None of those things are bad, and in fact they can be wonderful ways to prepare for the complexities of dating. But none of them are sufficient. Over and above any checklist is the need for discernment and confirmation from the Holy Spirit.

I think that Christian conversations about dating often shy away from the topic of discernment because it’s hard. Discernment transcends our notions of rationality, so it doesn’t make a great discussion topic and cannot be squeezed into a pithy list of advice. There is great mystery in discerning the Holy Spirit’s gentle proddings.

And yet James 1:5 tells us that “If any of you lacks wisdom, you should ask God, who gives generously to all without finding fault, and it will be given to you.” Discernment is a mystery, but it is a promise from the Word of God that we can ask for.

When asked for advice on how to know if you’ve found “the one,” married people often say something like, “when you know, you know.” I used to hate this answer, because it seemed so unhelpful and unactionable. Yet the more I realize how little I see and the more I become familiar with the Holy Spirit’s quiet guidance, the more I’m convinced that it must be true. I have no experience with the feeling of “just knowing” you’ve found the one, but I do know there is an unshakeable peace that covers what God ordains, and discerning it requires hearts that know their blindness, seek His direction, and listen for it carefully.

What might that look like, practically? I know I just said that discernment cannot be distilled to a list of actions or advice. But I do think there are ways we can grow in our openness to hearing from the Holy Spirit. I think it all begins with the admission that our sight is limited and that we need Him to guide us. And then, listening for that guidance could look any number of ways.

Perhaps it looks like praying when you catch feelings for someone — and asking God to take them away if they are not from Him. It definitely looks like reading Scripture and attending to the advice of older, wiser people who are more experienced and know you well. Perhaps a few failed relationships will be required to know how God speaks to you personally — more often than not, God meets us in the shape of our lives and we learn through trial-by-error. Perhaps discernment is cultivated by seeking His direction in small decisions so that it becomes second-nature for big decisions. If we believe that God is faithful, we must believe that He will meet us in all the ways we seek to hear from Him and follow His guidance.

In the end, I cannot say I know much more about life and faith and the mysteriousness of love than when I was fifteen. But now, I do know how little I know; in fact, the more I live on this earth, the more I’m convinced that I really do not know much of anything — about dating or otherwise. There is far more mystery in life than I feel comfortable to admit, but thank goodness that I know the One who knows all and can trust His direction!


For a list of resources on singleness, dating, & sexuality, see here.

For more Common Ground posts on dating, see the posts tagged “Relationships” here.

For a post by one of my favorite bloggers (Lore Ferguson Wilbert) on the necessity of Spirit-led discernment in dating, see here.

Leave a Comment

Your email address will not be published. Required fields are marked *

Scroll to Top