What a Failed Best Friendship Taught Me About Myself


It was a typical, winter Minnesota evening: dark, chilly, dreary, but the cold pierced my skin harsher, different this time. My best friend (now ex-best friend) and I sat across the dinner table from each other — let’s call her Sophie – and there was only silence. We both knew. This friendship was over, and there was nothing that could bring it back.

I was staying with Sophie for two weeks as I was beginning my month-long, cross-country trip from my home in sunny Los Angeles to New York. This whirlwind of adventures
was all before the trip of a lifetime: living and working in Italy for three months.

It was the perfect trip that got off to a painful start that evening in Minneapolis. Words were exchanged — so hurtful that they seemingly ricocheted off the windows and bounced back to hit my heart with twice the intensity. Lines were drawn in the sand that neither of us would dare cross once more.

This fight was the icing on the cake to years of fighting and an unhealthy best friendship. No matter how much we loved each other, at the end of the day, the healthiest and most life-giving decision was to let go.

A year later, the details of the fight matter less (a little less). More so, what I think about now is the indelible mark the friendship left on me, for both the good and bad. Losing this friendship felt a lot like getting older — inevitable but hard and, at moments, shockingly and devastatingly painful.

I got burnt out. Tired of showing up for a friend who forgot my important days or moments; burdened by the feeling of begging someone to be my friend; worn from having to constantly prove my worth as a good and valuable friend worthy of her time.

Prove my worth. This friendship made me question my worth constantly. I realized that the source from where I was looking to get it was the issue. It should have never been in another person, not even a best friend.

In my time of grieving and processing the loss, I wrote a love letter to myself, “You deserve the space and room you need to grieve this. You wonder how we got here, but we know. By wanting a friendship and the validation of another person so much so that you ignored your inner voice, that inner knowing that said time and time again it wasn’t right.”

The best way to love others is with open hands. The only way to love others well is by first loving yourself with grace, dignity, acceptance, and forgiveness.

I have come to terms with the knowledge that this failed friendship did not and does not make me a failure. There were lessons to gain from it. There was growth needed on both sides. This friendship allowed me to see myself clearly — my codependence, my need for validation in the form of others, my insecurity that allowed me to keep going back to a friend that had shown she did not value me.

Value. Valuing myself means listening to my instincts. It means leaving the table when love is no longer being served; it means being willing to lose someone if in the process I gain myself; it means not investing more than what is being invested in me.

In the end, I learned to value myself before I can expect another human being to do so- even if that human is… was my best friend.


If you find yourself in an unhealthy or imbalanced friendship, here are some questions to help you weigh whether it is time to let the friendship go:


Is this friendship life-giving?

My friendship with Sophie taught me the importance of seeing red flags and heeding them in any form of a relationship. With Sophie, I found myself constantly drained from caring for her, showing up for her, and giving to a friend who did not reciprocate. We had so many fights where I told myself I was done, but somehow, I always found myself hoping for her call. It was exhausting and far from life-giving. If a friend takes more from your life and you than they bring, then it might be time to let it go.


Is there competition in the friendship?

A healthy friendship revels in each others’ differences. Your best friend should be your greatest cheerleader in your strengths and your confidant to speak the truth in love in your weaknesses. I never realized there was underlying competition between Sophie and I until other people pointed it out. I played second to her often because I chose to. She was used to getting the spotlight, and I didn’t mind taking the passenger seat to her shine. You should never have to play small in anyone’s presence (especially a friend), but your friend should also encourage you to shine in all your greatness. 


Is there healthy change and growth on both sides?

I once read a quote that said, “Love is not repeat offenses followed by elaborate gestures, but it’s sincere repentance followed by changed behavior.” This friendship showed me the difference between mere words and a changed heart followed up with actions. Out of the many fights this friendship brought, the overall theme was always the same: an off-kilter, imbalanced friendship. Although Sophie would apologize, it never really changed. Acknowledging someone’s unwillingness to change is an important step to identifying an unhealthy friendship and letting it go. You cannot change someone else. After all, think of how hard it is to change yourself alone.