Dating · Men · Singleness

To All the Boys It Didn’t Work Out With


Once we went out on a date.

Or we had this “thing” going between us.

Or you asked me out and I said no.

Or I liked you, but you didn’t like me back.

Once you said some incredibly sweet words to me which broke my heart because I couldn’t believe someone would think that about me – and that I couldn’t love you back for them.

Once I said some sweet words to you, which also broke my heart because you couldn’t return the feeling, despite our dear friendship.

And now – I see you getting engaged on Facebook – and then I see you getting married.

And it’s perfectly clear why you didn’t work out for me. Because you were meant for her.

I felt horribly guilty at the time. Sad that I couldn’t feel more for you. Ever analyzing my feelings to death to see if I could change them. Or sadly wondering why your feelings for me couldn’t change.

But now it’s clear. God had a best for you out there, and it wasn’t me.

And this sovereignty of God’s – this full and complete control over every situation – is what I must rely on when things don’t seem to make sense with guys. I have to trust that their breaking my heart or my breaking theirs is part of God’s plan – and He had someone else in store for them that couldn’t be imagined at the time.

So what was even the point of us having something going on in the first place?

I think, that in every situation, God’s sovereignty was also at work to teach us something valuable.

I can’t speak for what the guys may have learned from it, but I know what I learned.

I learned in some situations more clearly what I do and don’t want in a future boyfriend or spouse.

I learned to cherish what the friendships gave me, even if nothing more came out of them.

I learned to be grateful for the encouragement and the kind words of affirmation that many of my guy friends have given me in the past.

I learned that none of us is immune to heartbreak, no matter how carefully we try to guard our hearts, and that mourning the loss of what was and what didn’t happen is okay and normal.

I learned that each person who comes into our lives teaches us something different about ourselves, and we need to be open to what we bring out in each other – and thank each other for that.

I haven’t always been the best at processing these lessons. Some haven’t come to me for months or years. Some I haven’t wanted to process, and I just wanted my way instead of the lesson.

But God is gracious about schooling stubborn hearts – and He has patiently revealed these lessons over the years. He has given me so much more understanding than what the naïve teenager once had – she who thought that by not dating, a person could avoid all sadness and broken hearts.

There is no way to avoid sadness and broken hearts. It’s a side effect of being human and loving other people – intentionally or unintentionally. Sometimes it’s incredibly painful to let go of someone you thought was everything you ever wanted because they had to gently say, no, I’m sorry, I’m not the one for you.

But after the pain subsides and the clouds of dark days are driven away, you see reality – that they were right, and they weren’t the best for you. And when their best comes along – or your best comes along – it makes so much more sense. And sometimes the best isn’t found in another person, but in a deeper relationship with God that could have happened no other way than for your heart to have its ties broken to another person.

Sometimes these tricky relationships won’t seem to make any sense this side of eternity. But that’s where God calls us to trust Him completely. We have to let go of our need to control the situation and our understanding of it and have faith that God knows what He’s doing.

It feels impossible sometimes, but God gives us grace for our weakest faith. Even as we whisper out, “I believe, please help my unbelief,” He is already answering and sustaining us on our dark days.

To all the boys it didn’t work out with – thank you.

Thank you for allowing me to experience small tastes of love, even if it wasn’t the “happily ever after” kind.

Thank you for being kind to me, even when heartbreak had to happen – on my side or yours.

Thank you for being patient with my imperfect ways of handling relationships.

Thank you for being faithful men of God who still inspire me to this day.

May God grant you the peace and joy that He’s granted me, and may you be used of Him, either with or without that wife by your side.

Because even if we didn’t work out, in God’s sovereign plan, He’s working it all out for His glory and our good.

And His story always ends with a happily ever after.


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