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3 Things I Wish I’d Known When I Was Single

As I look back, it is clear to me that waiting for marriage for much longer than I expected was for my good.

One of the greatest blessings of the years I spent as a single adult was being a part of the Boundless community as both a writer and occasional podcast guest. This pushed me to think about the challenges and opportunities of singleness — both the ones I experienced myself and those I heard from others who were also waiting for marriage.

It’s hard to believe that my wife and I will celebrate five years of marriage this summer. The time seems to have flown, but as much time as I spent reflecting on singleness as a single person, there are some insights that have become even more pronounced as I look back. Here are a few things I wish I’d known when I was single.

1. Be thankful when it doesn’t work out

I had more first and second dates than I care to count. Many times, I initiated and felt the awkwardness of the relationship not moving forward. It doesn’t matter why a relationship falls apart; it’s always hard. I’m sure at the time, I responded to the disappointment by saying something like, “I don’t know what God is up to in this, but I’m sure it’s good.” But I don’t think I really appreciated it as I do now.

Now I look back and I see clearly what a good thing the waiting was. God was doing a hundred things in my life that I couldn’t see at the time. He was teaching me to wait patiently and to trust Him when I couldn’t see the way forward. He was teaching me how to love others even when they might not love me back. Now I see that the future “yes” God had prepared for me was better than the many frustrating “nos.”

Likewise, I more fully understand how some of the challenges of singleness have made me a better husband and father. Before marriage, I battled loneliness, struggled against discontentment, and felt like I didn’t fit in with my married friends and loved ones. Now, I see these are challenges that helped me be less selfish and more humble with my family. As such, I wish I had spent less time questioning God about His plan and timing and spent more time thanking Him for all He was doing in my life, much of which I was unaware.

Of course, this good advice is not only for single adults waiting for marriage. One of the reasons Paul taught the Philippians to bring their requests before God “with thanksgiving” (4:6) was that there is always much to be thankful for in every season of life. God is always doing much more than we are aware of. So, we can and should thank Him for the goodness we can see, and we should thank Him for the goodness we can’t.

2. Contentment is a challenge in every season of life

As a single man, I thought and wrote a lot about contentment. My wife says one of her early impressions of me was that I seemed content in my life as a single adult. God was good to me in providing lots of work and community during those years. But I think any measure of contentment I had might have had more to do with the fact I kept myself so busy. This spared me from much of the sting of singleness.

In any case, married life has reminded me that in all seasons of life, there can be temptations to discontentment. When I was single, I battled feelings of discontent because I wanted to be married and have children. When I got married and had children, I felt discontent because I wanted to be further ahead financially so I could provide better. I think I fell into the trap of thinking once I was married, contentment wouldn’t be a struggle anymore. It still is.

Growing in contentment is a grace we should strive for and ask God to help us with right now. Learning to receive from the Lord both the good and hard parts of life is not something that marriage will magically whisk away. Rather, as God shows us areas of discontentment in our hearts, we should go to Him and ask Him to help us walk with gratitude for all things — both the good and the bad — that He has chosen to bring into that particular season of life.

3. Prayer while waiting

One of the most annoying pieces of advice I received as a single was, “Just keep praying.” As advice goes, this was tough to argue with, but it still felt discouraging. I remember thinking, I have been praying … a lot! My prayers for marriage could be summed up with the words, “Bring it … NOW!” Not a bad prayer per se; and bring it God did — at just the right time.

But I wish I’d prayed more along the lines of, “Father, I know You are working in my life through this season of waiting. Please teach me all You have for me to learn and then bring my wife along.” That would have been a more trusting prayer than what I typically prayed. I wish I had trusted God more in the waiting.

I believe God does some of His best work in us when we are going through difficulties. It seems counterintuitive, but as I look back, it is clear to me that waiting for marriage for much longer than I expected was for my good.

As I single adult, I believed God was teaching me something through waiting, but I think I mostly thought, “I’m still waiting because I’m not ready yet.” Now I see that God’s plans and work were much bigger and better than I could then see. He was preparing me for future challenges, like decisions around career and what city to live in, that I couldn’t possibly have understood.

I wish I had chosen to trust Him more fully. I wish I had prayed boldly for marriage and for help growing through the season of waiting — and gratefully trusted His plan for my life.

Copyright 2021 Andrew Hess. All rights reserved.

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About the Author

Andrew Hess

Andrew Hess is a Sr. Communications Specialist at Compassion International. He formally served as the director of content at the White Horse Inn and editor of His writing has also been featured on the Gospel Coalition. He lives in Colorado Springs with his wife Jen and their young son. Andrew and Jen met at the very first Boundless Pursuit conference at Focus on the Family in 2014.

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