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  • Writer's pictureStephen Hart

83rd Time's the Charm

Updated: Nov 21, 2023

In response to my last article, several people with a similar situation reached out with a basic question: how? After suffering an immense loss of my person, the idea of finding another in this life, feeling that kind of love again, is daunting. Seemingly impossible. If you know, you know. This article is my answer to that question. I am certainly not suggesting my way is the only way, this process was in parallel with immense personal work and therapy, but this is how I went from total devastation to feeling real, expansive love again with a new partner.


I did some research in preparing for this article. Between the time I went on my first date to the moment I experienced love again for the first time since Karina passed, I went out with 83 people. 

83 is not a small amount of people. 83 times I took a deep breath and showed up to be vulnerable with a stranger. 83 times I wondered if I was attractive enough, valuable enough, funny enough, interesting enough. 83 times I had to decide what we should do, what to talk about, what to wear. 83 times I wondered, will they accept me with Karina still in my heart.

82 times I learned something I needed to learn so I would be ready for 83. I’ve found love again and it feels amazing, but more on that in another article.

It took a major mindset and lifestyle shift to get back into dating again. From being engaged, planning a wedding, and preparing to start a family, to single and starting from scratch, it felt like I tumbled down a mountain and had to pick myself up and relearn how to climb. I knew that what I wanted in life, to experience love again, wasn’t going to happen without effort, so I decided to go for it. 

In the beginning, I didn’t know how to date. I couldn’t relate to most people around me. I couldn’t empathize with other people’s problems. I cried pretty much every day, if not several times a day. Frankly, I didn’t know if and when I would even have the capacity to emotionally connect again. In my life, love and extreme pain are intimately entwined, so there was a lot of fear around opening up to love again.

After my mom’s passing, I remembered how hard it was to open my heart again. Karina had to pry it open, and it took months if not years. Like pealing away thick layers of clay to get to where I could feel again. It was a major challenge for me, but ultimately so rewarding. 

This time around, though the pain magnitudes greater, I knew what I was up against and I refused to let my heart harden again. Working closely with my therapist, she said one thing that became my mission statement for this process:

“Stay vulnerable, not too comfortable. Keep pushing your boundaries and be compassionate with yourself when you wobble.” She helped me to discern when was the right time to start dating again and helped me stay aligned with the intentions that would support my highest path. 

Along with my regular grieving practices and therapy, dating intentionally has been a major part of my healing process, leading me along a dark and uncertain path toward the light of love once again.

Below are the guidelines I developed to help keep me aligned with my intentions:

  1. I am not trying to replace Karina. I still have her and don’t need another. If I find myself comparing a new partner to Karina, I need to back off and reset. Comparing is a sign that I’m trying to fill a void, and will do no good for anyone. 

  2. See all relationships as a mirror. What can I learn about myself as I show up with another? Since I’m not replacing Karina, what do I want in a partner now? What values are important to me? How do I want to feel with another? What do I not want?

  3. Stay positive with the dating apps, if I decide to use them. Just because everyone else is frustrated by them, doesn’t mean I have to be. How can I use them as a helpful tool to enhance the process? How can I be intentional, avoid the pitfalls, and stay positive as I navigate them?

  4. Appreciate the soft endings. Karina was a hard ending, the worst. If a relationship doesn’t work out, and it’s anything better than a world-shattering experience, celebrate that. Sounds weird, but this really helped.

  5. Be honest with everyone. My story is not anything to feel shame over. Share what I know, share that I’m still figuring things out, and allow them to decide if they want to be a part of my life. I don’t need to pretend I’m better off than I am.

  6. Even if someone is not a romantic connection, they are still a human being. I can still learn a lot from someone who I don’t see as a partner, so treat everyone with respect and appreciation. Most people fell into this category, and they have been so valuable to me on my journey. 

  7. Stay persistent, and ignore the outer and inner judgemental voices. Other people will not understand what I am going through and may judge me for it. As my therapist so eloquently put it, “If someone judges you, fuck ‘em. This is your life to live, and it’s all you got.” This lesson was very, very helpful. 

  8. And most importantly, stay compassionate with myself. I’ve been through a lot, and I’ve chosen the challenging and vulnerable road towards expansion and love. It is not a linear path, it will come with some very hard moments, mistakes, and pain. It’s okay to not be okay sometimes, find compassion for myself in those moments especially. 

With that, I asked the universe to send me the right people at the right time to help me further my expansion as a human, a man, and a spirit. I decided I would use the dating apps and have a good experience with them. I understood that it would take time and energy, that people can be flakey, and that I would get rejected. Instead of resisting, I decided to let it all be a part of the process. Anyone who rejects me is self-sorting themselves out of my life because they don’t align with what I asked of the universe. 

I trusted the right people would filter through, and that’s exactly what happened.

I met 83 people, most of them were non-romantic, many were only one date. But each woman that I shared space with taught me something about myself. 

I learned how to feel, observe, and communicate complex emotions. I learned to show up grounded in my masculine energy and allow my feminine to reveal over time. I learned to be honest even when I know my truth may hurt another’s feelings, and that it is not my job to protect another’s feelings by withholding how I feel. I learned to create a safe container for a deep connection and open conversation. I learned to hold tension when I’m apart from someone I’m interested in. I learned how to invite my sexuality into the spiritual realm and talk openly about sex, pleasure, and desire without shame. I learned how to trust that everything will work out as it should, and replace dread of the unknown with excitement for what’s to come, the experiences I’ll get to have, and the people I’ll get to meet. 

Most importantly, I learned that I cannot show up well for another if I’ve lost love for myself. 

In my life, I feel fulfilled with my work and content with my lifestyle. Readying myself for a loving companion, someone to share the joys of life with as I had for 7 years with Karina, was my priority. So, despite the moments of self-doubt and the judgments from others that I faced, I persisted. It would only happen if I put myself out there, over and over. Over and over. Over and over. The 83rd time was the charm. 

This relationship might last another week, or another 50 years, and either is okay. In the not-too-distant past, I felt it was impossible to find a partner again, and each failure reaffirmed that notion. I know now that that is not the case, and I am reminded of what loving someone feels like and what it feels like to be loved. 

If I could speak to my earlier self I would tell him to keep going, stay positive, and trust in the process, it’s coming. We have no choice but to continue, onwards and upwards.


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