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Is Your Love Life Experiencing the Dark Night of the Soul?

Is Your Love Life Experiencing the Dark Night of the Soul?

Have you ever visited a place inside yourself that was so painful, so lonely, and so desperate that you literally felt like nothing made sense anymore? You could be experiencing what many call “the dark night of the soul.”

The dark night of the soul can rip through you, almost relentlessly. You might mistake it for a deep state of depression, but it’s not. A dark night of the soul can eventually bring an enormous amount of gifts. Especially when it comes to relationships.

I wanted to share this because I know many of you are looking to find a soul connection. And right now, you might feel like you’ve hit a wall. But I’m here to remind you that, as Ralph Waldo Emerson once wrote, “every wall is a door.” The dark night of the soul may feel like an obstacle, but it can be the biggest opening to love you’ve ever experienced.



I know this because I went through one myself back in 2011/2012. I’m also experiencing it again now. Are you in the middle of one too? Let’s explore the possibility together.

What Is the Dark Night of the Soul?

The best description I’ve heard about the dark night of the soul comes from spiritual teacher Eckhart Tolle.

According to Tolle, the dark night of the soul shifts your entire perception of life at a very deep level. Suddenly, all the things that used to give your life meaning start to feel meaningless. This creates an internal crisis.

Shocking events, such as the death of a loved one, a natural disaster, or simply the loss of something that was closely tied to your self-worth tend to trigger a dark night of the soul. Your mind simply can’t cope with the new realization or circumstances it has to deal with.

While this can look like a mental health breakdown, it’s actually a spiritual awakening process. The old framework you used to make sense of your life before no longer applies. Because of that, you end up in a dark place. So to get out of it, you have to transform.

And like a phoenix out of the ashes, you rise. But now, the meaning you find in your life isn’t tied to people or external things. It comes from a deeper, more eternal place inside — your soul.

The purpose of the dark night of the soul is to expand your capacity for love. If you’re experiencing one, that means you are courageous enough to seek a greater understanding of yourself. So hold on. Better days are coming.

My first dark night of the soul happened to me several years ago. I was searching for the meaning behind dating, love, and relationships. I wanted to know if love was real. And so I went on what turned into a spiritual journey of self.

The 100-Date Experiment: My First Experience With the Dark Night of the Soul

In 2011, I found myself in my dorm room, completely lost and alone. Midway through a social experiment that I had chosen to conduct in order to better understand dating, I sat on my twin bed, consumed with fear that I would never find love. That night, I cried out years of loneliness and heartbreak. I cried over past relationships and pain rooted in childhood; it was a childhood that didn’t include models for romantic love.

My parents were never married, and for me, a household that included two loving adults was nonexistent. I spent my younger years flanked by the issues of having an alcoholic single mother and a financially destitute father. All of that, coupled with subsequent heartaches, burst from me in torrential sobs until I fell into a deep slumber.

When I awoke, 25 years of incessant, internal chatter had gone silent. It was then that I realized that a social experiment I had been conducting was not simply a research project about understanding the behavior of others but a chance to better understand myself and to heal.



The Transformation

I realized there were things I needed to change in order to attract my perfect partner. My 100-date experiment had exposed chinks in my own armor that needed fixing.

By the end of 2011, I wasn’t the same girl who had started the research project. I was somebody else. I had become a woman — a good woman. Humble, kind, vulnerable, perceptive, and all of these things that I’d never been before in my romantic relationships.

I was the real me. Not the “me” that used to subconsciously beg for validation; who thought that marrying a professional athlete or CEO would prove that I was “enough”; who would hide unflattering information from potential suitors at the expense of showing them who I really was. I was no longer the “me” who had previously hidden behind sarcasm to never let anyone see the scared little girl inside, or who had thought that a 100-date experiment would be a research project about other people and not myself.

The process transformed every ounce of me. Dating 52 men (101 dates) taught me that love was possible. In fact, it wasn’t only possible, it was available at every moment for every person in every place, and the only thing I had to do was drop my ego and believe that I deserved it to find it. And when I did, I discovered that love was everywhere. It was all around me.

If I could teach my clients only one thing, it would be this: Love is an orchestra; it’s an ocean. Love is in every breath we take, it’s in every step, every word. It’s in our darkest moments and it’s with us when we shine. Love is always available.

Sometimes we just can’t seem to access it. I know I couldn’t. I’d built walls to protect myself from losing it again. We all do. But then I learned how to take those walls down. And it was scary.

My Current Experience With the Dark Night of the Soul

Fast forward to 2020. During corona, I hit rock bottom. Not unlike others, I found myself in a state of shock and grief and that led me into a downward spiral of drinking. At my lowest point, I agreed to attend a recovery meeting.

When I did, I was surprised at how much resonated with what I teach in my own coaching program, as well as in coaching programs I participate in as a student. I didn’t know recovery would be such a spiritual journey. The process set me off on a soul search vision quest to find meaning in my own life.

Though I’ve been in a happy relationship for eight years, I’ve been questioning a lot lately. At times, it can feel as though we’re just going through the motions. With droves of our friends getting married, buying houses, and having kids, there’s an underlying current of pressure to follow the herd.

But with each of us coming from divorced families, following the herd can feel scary. We’re both afraid of where those herds will lead us. And we’re not exactly the types to blindly follow without conscious examination of our decisions.

Hence, when Tom and I began having serious discussions about “next steps” in our relationship, I felt swayed to examine my authentic feelings about whether that was truly right for me.

Vision Quest 2020

I decided to go on a solo vision quest to reconnect with my roots and examine my own feelings, apart from the pressures of my partner, my friends, or my usual patterns. I’m on the journey now, and the quest, combined with what I’m learning about my own addictive tendencies in recovery, has me in a lost state of total confusion.



I recognize that it’s always darkest before the dawn, but in the void, there is so much unknown, so much potential, so many different trajectories. It feels unsettling, as though any path forward could lead to sudden death. It feels as though everything I’ve always known could be completely abandoned and replaced with something new. It’s the proverbial fork in the road. Do you take the path that you know or do you take the road less traveled and see where you end up?

Promise of the Future

Back in 2012, I was able to completely transform unhealthy patterns in my selection process that led me to the best relationship I’ve ever known.

During that first dark night of the soul, I had no idea what lie on the other side of the veil. But I did have a glimmer of hope that I might find love.

Now, I am in a similar position. I know where one path could lead but there’s another path calling my name too. One that doesn’t know its own ending. Time will tell, but I have faith that we wouldn’t be called to go through it if there wasn’t a better future for us on the other side.

Are You Experiencing a Dark Night of the Soul?

I saw a brilliant piece by author Brianna Wiest that really captures the signs of the dark night of the soul. I’ll describe a few of them here — you can check out her article for the rest.

Signs You Might Be in the Dark Night of the Soul

  1. You feel lost or stuck. That’s because the checklist of “nice things” and rules you’ve been living by are no longer fulfilling you. But you don’t know how to live any differently, so you’re frozen.
  2. Vivid memories of events and people you haven’t thought about in years start coming up. This is your subconscious starting to make its way into your conscious awareness.
  3. You play more. You might feel the urge to be silly, or joke around more than usual. As weird as it sounds, you are rediscovering your innocence.
  4. Freaky coincidences start to happen. The universe is trying to tell you something. Pay attention and listen.
  5. Spirituality and Eastern philosophies start to interest you. These areas of study provide lots of guidance during an existential crisis such as this. You may find yourself drawn to them.
  6. You’ve stopped caring about impressing people. What’s the point, anyway? Suddenly, everything external has lost its power over you.
  7. Your sleeping and eating habits have gone haywire. Your body is recalibrating to your new energetic frequency. Get ready to say hello to a whole different you.
  8. Social conditioning becomes really obvious. You start to notice that people tend to make decisions according to socially prescribed values rather than their own feelings.
  9. You have the urge to stay put. We’re all inside these days because of corona, but secretly, you’re glad — because you’ve been feeling the urge to withdraw and go internal.

Dark Night of the Soul: Wrap-Up

Your own dark night of the soul could mean many things. I believe that it often happens right before you meet your life partner. But it also could be a call to transcend the mundane.

Your soul may be ascending in order to elevate you to something better than you’ve ever known. It can also give you a chance to explore your own psyche, negative relationship patterns, and habits so can transform yourself and your current relationships.

Ultimately, only you can make sense of what’s happening to you. That’s the journey, after all. The call is for you alone to access your own buried inner resources and birth a new version of yourself.

If you’re experiencing this now, I hope you read this and find hope. Even as someone who’s been through this, I still can’t tell you how to resolve it — but I can tell you that in the end, it leads to amazing things.

So, don’t give up. And do reach out to me if you are looking for support along your journey to find love. I would be honored to help you discover happiness and success in your relationships, starting with an intro Zoom call and possibly 12 weeks of one-on-one coaching sessions, also known as my Signature program.

Until we meet — take good care of yourself.



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