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Dating

How You Know When It’s Time To Let Him Go

Debating if you should stay in your current relationship? Here are several scenerios for when it might be time to let him go.
I'm Stephanie May Wilson!

I'm an author and podcaster and my specialty is helping women navigate big decisions, life transitions — creating lives they love.

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We are a hopeful bunch when it comes to love. We’re hopers and dreamers and hold-onto-ers. We push through the hard times and refuse to give up, and that’s one of the best things about us.


We believe in love and fight for it with everything we have. That’s the strength that lies in the heart of a woman.


My heart’s always had a knack for hope and in most areas of my life this has been a great thing. But in other areas of my life, hope has been excruciating, something I wish I could have de-programmed altogether.


A few years ago, God told me who I was going to marry. I was positive. I had heard it, and felt like everything around me seemed to confirm it. For almost a full year, the prayers people prayed, the scripture I read, the circumstances that unfolded, everything seemed to be pointing me in the same direction: This is your husband! This is who you’re going to marry!


I prayed, and I believed, and I trusted with my whole entire heart, even when things weren’t going well, even when my circumstances were telling me I’d heard wrong.


We weren’t on the same page. I was pursuing our future and he was moving on. I was running after what I thought God had told me, but he wasn’t getting the same message.


So with hope spurring me on, I tried harder.


I thought this was a test of some sort, that I just needed to keep hoping and keep praying, and that somehow what I thought God had told me would work out.


Have you ever found yourself in a place like this?


We begin relationships with such hope, such energy, and such a desire to see them succeed, that we don’t know what to do when things aren’t going the way we hoped.


Maybe we just need to try harder, or prove that we’re up to the task of loving someone for better or for worse. Maybe we just need to pray more, or fight for it more, or wait just a little longer and it’ll work out.


This is a painful place to be, because here we’re stuck between hope and our circumstance — between our desire for something to work out and the fact that it currently isn’t.


It’s even harder to know what to do in those situations – to hold on, or to finally give up.


When do you pull the plug? When has it been long enough? When is it time to stop hoping?


I can’t and won’t tell you what to do with your hope today. But I’m going to (gently, I hope) give some scenarios that might suggest it’s time to let go.


It takes a super-human amount of bravery to take a hard look at your situation, but if you find yourself stuck between hope and giving up, I’m going to ask you to try.


It may be time to let go if:


– The person is in a relationship with someone else


– They haven’t reciprocated your feelings for them


– That person is consistently mean to you or makes you feel small


– You’ve broken up and they haven’t suggested they may want to get back together


– You’ve done everything you can think of and it still isn’t working out


– You’re the only one pushing the relationship forward


– You often wonder if you're settling


– You find yourself glorifying their good actions and justifying their bad ones


– You're holding out hope that he's going to change


When you’re holding onto hope for a relationship, admitting to one of those things is incredibly painful. But it also can be one of the best things you do for yourself. I know how it feels to waste time on something that isn’t working when there is something else out there that might.


I held onto my hope for that relationship for a long time. I thought I had heard God correctly, and I could name a thousand reasons why we could and should end up together. But no matter what I did, I couldn’t make it happen. And when I finally looked at our situation honestly, I could see things weren’t right. If they were, I wouldn’t have to force it.


Our circumstances, his actions, our interactions, everything was refuting what I thought I’d heard God say. And eventually I had to consider that maybe I’d heard wrong.


I didn’t want to let go of our relationship. Because not only was I losing someone I cared so much about, in the deepest part of my heart I was afraid if this didn’t work out, maybe nothing ever would.


But just like God always does, when He asks us to let go of one thing, it’s right up His ally to give us something better.


I eventually gave up on that relationship and let go of the hope I’d held onto for so long. I didn’t know how the story would turn out, but I knew I trusted God enough to let go and find out.


A few months later, I went on my first date with someone new.


He came into my life without warning — pursuing me, and caring about me and investing in our relationship. I didn’t have to push or shove or hope him into my life, he came on his own, and he fit.


If I hadn't given up on that relationship, I never would have met my husband.


We are the best hopers. We refuse to give up, fighting for the people we love, and for the relationships we believe in. And this is a beautiful trait, something wired into us for the time when we will fight for one person for the rest of our lives.


But before then, we'll never know what God might have for us if we're too busy fighting for a relationship that isn't fighting for us right back. Sometimes the best things can happen when we unclench our fists and bravely let them go. Because only then can we receive the better “yes” God is just waiting to give us.



Check out these related blog posts and podcast episodes:


The 5 guys you don't want to date (blog post)


Girls Night #29: How to Know if You’re in a Healthy Relationship (and What to do if You’re Not!) (podcast episode)


Girls Night #100: How to Know if You've Found “The One” (podcast episode)

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Debating if you should stay in your current relationship? Here are several scenerios for when it might be time to let him go.

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  1. Melissa Mills Blakey says:

    Love this because it’s spot on! I could have used your words years ago when I was holding on to someone I couldn’t let go of. Hoping someone reads this who really needs to hear it today because this, my friend, is TRUTH!

  2. Helena says:

    Glory, hallelujah. Thanks for writing this, Stephanie. It’s so easy to second-guess, but this truth is timely. You’re a huge encouragement ♡

  3. Constance says:

    So encouraging to read this today. The message is empathetic and in the best way, challenging. You couldn’t have written it any clearer. I pray more women receive this revelation just as you did. I receive it. Thanks Steph

  4. Kiara says:

    God does wonders! I was literally going through this situation when your post popped up in my email. I pray God continues to use you as a gift to help encourage and inspire others in their time of need.

  5. Talia says:

    great blog and great list. can be hard to know when its time to say goodbye when you’re designed to be a hoper. well said.

  6. Kacie says:

    This is a great list and I love you for letting God teach you and then vulnerably baring those lessons. This one was so confusing and painful and lasted for so long, and I LOVE getting to see The Lord redeem that time, not just in your marriage, but now in sharing the story and offering a “me too” to women (and probably men, they can be great hopers, too!) who need to hear it.

  7. Emily says:

    I needed to read this today. It’s comforting to know that there are many others can relate to heartache caused by having to let go. Right now I am trying to get through a breakup where the relationship was very fruitful and exactly what I had imagined for myself. Although I am struggling, I’m choosing to place my trust in God’s hands because He has my best interest. Thank you for your gentle and honest words!

  8. Kimmy says:

    Oh goodness this was good. Thank you. Letting go can be such a process …. But when we manage to …. And finally realize our heart has healed …What a relief !

    Thanks for reminding us we are never in this alone 🙂

  9. Scotty says:

    Wow. Been here before.

    I’d say another one for the list is “You have to explain your relationship for a long period of time for any outsider to ‘get it.’ ” I say this because good, supportive relationships are normally more simple. If you two are the only ones who understand it or “it’s not how it seems; it’s just this way because. . .” then you might be getting caught in a complicated love/hate vortex. This was a big wake-up call for me with my ex-boyfriend. I realized that my explanations were getting more and more complex in order to convince myself and others that he cared about me as much as he claimed to. Hard realization, and it was really REALLY difficult to let go.

  10. Kelsey says:

    I really enjoyed and resonated with this post as I have a recent similar story. I really loved how you connected the hope aspect, it helps reconcile why we stay in unhealthy relationships for too long. Thank you for your insight! It’s incredibly encouraging 🙂

  11. Makayla says:

    Your posts always have perfect timing 😉

    This is my favorite line and something that I will continue to wait for and date for even though it’s becoming so exhausting for my heart:

    “I didn’t have to push or shove or hope him into my life, he came on his own, and he fit.”

    As always, thank you for sharing.

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