failed relationships.

Today’s post is a day late for Failure Week, but no one cares except for me, ha ha. I am trying to wrap up a few things before a blog break but I’ve been in the thick of a lot of hard stuff this week. In the midst of it, I have been thinking so much about failure and how pervasive fear of it can be.  So much has to do with expectations of ourselves, of others, of the forces of the world.  It makes me think of a meme that some of you have probably seen at some point around Facebook–“When you release expectations, you are free to enjoy things for what they are instead of what you think they should be” (Mandy Hale). It sounds good but inside my guts scream, “but they’re not the way they should be!”

So far on Failure Week we’ve talked about failure and failed parenting and failed faith.  Today I wanted to touch on another area of failure that has been so difficult for me to reckon with over the years and is definitely tied to expectations and wanting things to be different than they sometimes turn out–failed relationships.

I am a loyal person. I stick by my friends for life. I may not always be available in the way I want to, but when I sign in for a relationship, I do not take it lightly.

A big chunk of years ago one of my best friends ditched me over theology. It was brutal, seriously one of the most painful things that happened to me relationally because I had let her into the deepest parts of my life  and never, in a million years, would have expected that she would break relationship with me. And over God stuff of all things! But it happened.

Here’s what I did for a long time–I kept going back and trying to make it work. I kept having one more phone conversation, one more go at working it out, one more attempt to somehow make it work.  And then I remember the day when I knew I had to quit trying. When I realized I had done everything I possibly could and it was time to do what is hardest for me–let go.

Just let go.

To celebrate what was about that season of my life with her and accept we didn’t have a future.

The same thing happened to me 11 years ago, too, with a different set of circumstances but some of the same themes. It brought up all those old feelings and a desperation inside to not let it happen again. But by this time I had done a lot more healing and recovery work and could better identify my codependency and how much I was giving up myself to try not to get rejected. But the reality is that I still tried way too hard, apologized for way too much, and compromised myself to try to make it work.

In the end, it didn’t.

Another failed friendship.

In the past several years, I have a no-contact-anymore-relationship with a family member that has been really hard because it violates that thing inside of me of always-trying, always-working-it, always-being-the-one-that-was-somehow-responsible for the relationship. As I kept getting healthier, I knew I just needed to let it go.

To truly let it go.

To cut the ties of trying, at least for now.

It’s such a weird and foreign feeling for me because I’m so used to working it.

Some days, it feels like failing, and I question myself, “Is there something else I could do, should do, God is prompting me to do that I’m somehow missing?”

Other days, I see it more clearly and let myself off the hook.

Let it go.

My guess is that so many of you out there know what it feels like to have failed relationships. So many are far bigger than friendships. Maybe they are divorces, estrangement from family members, painful breakups, church and ministry relationships, or some other weird thing that happened with friends or people you love that make relationship now impossible.

Like so many things related to failure, it’s easy to dwell on them.

To replay the tapes, to go back and try to figure out all the ways we could’ve, should’ve, would’ve, of all the ways we screwed it up or did too much or not enough or anything in between.

The bottom line: It’s easy to get stuck in the past.

I’ve been trying to re-frame how I view some of these failed relationships from the past.

They aren’t failures.

They are parts of my story.

Even though they didn’t turn out the way I expected, they were still somehow gifts to me for that season of my life.

This doesn’t take away the pain of losing what I had hoped for or put a shiny bow on things.  Grief is real.

However, it does help me loosen the shame and see the good of what was because there usually always is some.

Something to celebrate.

Something to honor.

Something that made us who we are today.

It also has been helping me be more grateful and present in the relationships I am in today. 

Even when things are hard, I do feel less desperate, more peaceful. More free, less scared. More committed to showing up and doing what I can in the moment, a little less centered on controlling out of fear. More tender, less guarded. More willing to honor that I’m always learning, growing, transforming through each and every relationship.

A little less worried about “failing.”

Kathy Escobar

Kathy Escobar is dedicated to creating safe and brave spaces for transformation and healing in real life, online, and outside. She co-pastors at The Refuge, a hub for healing community, social action, and creative collaboration in North Denver, co-directs #communityheals, a non-profit organization dedicated to making spaces for transformation accessible for all, and is the author of Practicing: Changing Yourself to Change the World, Faith Shift: Finding Your Way Forward When Everything You Believe is Coming Apart and several other books.


  • Kathy I do relate to your story. Earlier in my life I held on to relationships that were sucking the life out of me. I too have learned the importance of letting go. It is never easy. The hardest learning for me was my first marriage. To sum it up two desperate people came together for a very unhappy relationship. After five years I finally realized I needed to make one last try to save the relationship or let it go. I never thought I would be the one to end the relationship. I was worried what others would think of me. I did end the relationship. It was one of the best choices I have made in life. However I am thankful for what I learned about myself in the relationship. I now have been in a fulfilling relationship with Jen for 11 1/2 years. I am very thankful. Thank you for sharing some of your struggles and joys. You remind us all that we are never alone.

  • Hi Kathy, thank you so much for this post. I discovered a year ago that I have co-dependent tendencies, and then more recently discovered that some of my close family relationships are not balanced or loving. I am trying to move away from a few family members and am going through the whole denial/acceptance thing which I am finding hard. Like you I kept trying to make things work, and am now trying to have the relationship where I am not following old patterns like before. Thank you for sharing your experiences. I find it hard to know how to have a relationship where I am assertive and not following my co-dependent ways, yet at the same time in the context of loving Christianity (turning the other cheek is not the best advise to give a codependent!).

  • Oh boy…

    I have “no contact” family members.

    I understand what it is like to keep going back and trying to fix those relationships.

    Was raised with a narcissistic family. (16 years to leave) Left that for a narcissist husband. Left that for a narc relationship with church leadership. Left that for a narc friendship. And here I the middle of refusing to be co-dependent anymore and wanting to have healthy relationships but being too freakin unsure of myself to step out.

    I don’t want to make the same mistakes again. More failures. More codependancy.

    LOLOLOL I give myself credit, I recognized the narc/codependant pattern in the friendship and backed off quickly.

    :/ ugh

    In my heart I just want to be around people. Connect with people authentically. To be a part of a community…part of a family. To help and be helped. To love and be loved. To give and receive. I miss conversations. I miss connections. I miss feeling like I have family. I miss smiles and silly conversations. I miss alot because I live in my cave right now.

    Maybe miss isn’t a good word…you have to have experienced family in order to miss it. I *yearn* for family.

    I want the real deal. Im slow to step back out again. I’ve lived like a hermit for three years now. After the last church relationship blow out… all I see is a string of failed relationships/church experiences where the only thing that is the common denominator is ME. Im somewhere in the tail end of processing all this and trying to step back out into friendship lane.

    I’ve decided if what I miss/need/want/yearn for isn’t around… I’ll be the catalyst to create it. There are others like me in my community. I am not alone.

    Rough day lol.. have binge read books and blogs today…but I found your blog and its a long tall cold drink of water in the middle of the edge of my wilderness that I can’t stop drinking.

    I read all these posts and realize exactly **not alone** I am.


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