Messy Faith,  Personal and Spiritual Ramblings,  Recovering Perfectionist

Failed courtship: when you trust and obey but your heart still gets broken

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I was 18, and one small mistake during my freshman year of college had turned my world upside-down. I had said goodbye to my dream college and was now struggling to make sense of the doubts and confusion left behind. I was so broken.

I thought that because I was living a life “surrendered” to God and “in His will” that everything would work out in my life for the best. Now that things had whirled out of my control, I sought for answers. Whose fault was this? Was it mine? Was it the institution’s? Or was it just God’s plan?

And for what purpose had all of this happened?

Little did I know that the questions would just keep getting bigger.


I had a boyfriend-almost-fiancè with whom I was dreaming of a future in missions work with the military. Our relationship had all of the right ingredients that I believed were needed for success: parental permission and involvement, submission to God’s will in the relationship, and commitment with the intention of marriage.

We had said our goodbyes at the same time I had said goodbye to the college we were both attending. He was also sitting out the upcoming semester for financial reasons. Our plan was for both of us to work for a while and then marry in the following year or two.

As this story is not completely mine alone to tell, and the details are unnecessary, I’m just going to skip to the part where I found myself with a broken heart and yet another broken “perfect” dream.

Less than three weeks after I had said goodbye to the “perfect” college I also had to let go of what I thought was the “perfect” relationship.

It was an ugly three weeks. My family and his family went to war. Again, accusations were hurled in multiple directions from multiple people. My intentions were again drawn under scrutiny. Things that I said were twisted and misunderstood. I was called horrible, ugly names. He told me he just didn’t love me anymore. 

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God, dear God, why? 

Why would you lead me to a college that would just accuse me of having a rebellious heart? Why would you lead me into a relationship with a man who would just walk away and leave me with a broken heart? 

God, I thought that if I wanted to please you, to do what’s right, to follow your plan – that things would work out. But instead, everything has fallen apart!! What are you doing?!?!?!

A broken college experience.

A failed courtship.

Now, I didn’t just feel ashamed and worthless because I couldn’t follow rules. I also felt worthless because I had “given my heart away” to someone who I wasn’t going to marry.

To say I was broken was an understatement. 

{Related: Harmful Courtship Teachings: the Myth of the Construction Paper Heart}

Legalism sets people up for extreme disappointment. Following a set of rules (especially when it comes to premarital relationships) is supposed to please God and protect us from a broken heart.

The message that I believed for so long was this:

If we do right, God will be pleased with us and bless us.

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When we walk with the Lord In the light of His Word
What a glory he sheds on our way!
While we do His good will, He abides with us still,
And with all who will trust and obey

Not a shadow can rise, Not a cloud in the skies,
But His smile quickly drives it away;
Not a doubt or a fear, Not a sigh nor a tear,
Can abide while we trust and obey.

Trust and obey, for there’s no other way to be happy in Jesus
But to trust and obey.

But I had trusted, and I had obeyed. Over and over and over I had trusted and obeyed. But what I was experiencing wasn’t glory. It wasn’t a cloudless sky. I didn’t feel like Jesus cared about me at all, let alone feel like He was abiding with me.

I did everything right, and it still didn’t work out. 

when you "trust and obey" but your #heart still gets broken - the wilderness between #legalism and grace part 4 at

My thoughts read like something out of the book of Job as I grappled with the same questions that Job and his friends did:

Whose fault is it?

Legalism focuses on works – doing the right thing to earn the approval of God. It is fleshly and self-serving. So when things don’t work out as we think they should, we search for somewhere (some person who has done some wrong action) to place blame.

I spent the following weeks and months scrutinizing and rescruitinizing every action of mine. Some days I justified myself and washed my hands in innocence. Other days I was overcome with guilt and shame, blaming myself for everything. I knew I had made some mistakes, but surely nothing big enough to warrant my whole world collapsing in on itself. My mind vacillated between blaming the people who had hurt me, blaming myself, and even blaming God.

What am I? Some little pawn, a chess-piece in your sick little cosmic chess game?

Thus began my wandering in this wilderness, leaving behind between a world where keeping rules failed me, yet unable to even dream about a promised land of rest.

I wish I could tell you I came to some great understanding of why these experiences happened to me. I wish I could tell you that I’ve made sense of the whole blame game and determined exactly who was at fault. But life just isn’t that simple. This is a world full of imperfect humans who do imperfect things reigned over by a sovereign God who has plans for them all. I can’t provide the answers for the mysteries of the universe.

But this is the hope I can provide:

Over time, God brought me healing. He didn’t provide me all the answers, but he has given me some. He has used me and my story to bring comfort to others. And best of all, he has changed me through it, and used it to lead me right into his rest and loving grace.


I do hope that you will stick with me during the rest of this series. There is so much more I want to share and so much more hope and clarity I want to offer. I promise the good parts of the story are coming! 

Have you ever had your heart broken by a relationship gone wrong or a dream unfulfilled? Have you ever found yourself trying to find the answers to the blame game? Have you ever “done everything right” and still had it all go wrong? Please feel free to share your own experiences in the comments.  


This post is part 4 in a blog series that I have entitled “the wilderness between legalism and grace,” in which I share how I came to realize that I had an incorrect view of God and self and how I became free of the system of legalism whereby I was trying to earn God’s favor. You can view all of the posts in the series here on the series landing page.

It is my prayer that Christians who are grappling with these concepts can find clarity, hurting Christians can find comfort, broken Christians can find healing, and tired Christians can find rest in God’s grace by walking through my story with me. 

To view all the posts in this blog series, visit the landing page.

Next post, part 5: when you’ve been hurt by legalism, hold onto faith

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