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Dating with the End in Mind

The other day, while having a beer with a gal pal after tennis, the topic of dating came up, most notably around my dating situation. I shared that I had recently ended a relationship with a fellow I had labelled as “the one.” The “One,” quite the concept, quite the label. The weight of expectation attached to it is hefty and almost impossible to achieve.


As we chatted further, I described that I was taking a new approach to dating, focusing on who I want sitting next to me as I move toward death. Lara laughed and said my next book should be “Dating with the End in Mind.” And although a joke, it got me thinking….


In 2018 my second husband, Don, died of cancer. We had only been together for five years, and our relationship was primarily centred around his illness and eventual death. This experience ignited a bold, new force within me, motivating me to make fierce choices. I've sold the family home; quit a stable job or two; became a certified coach; started my own business, learned to play tennis, built a new home; met new friends; travelled alone (until covid stopped me), and I am writing a book. I am constantly encouraging my kids to be brave and bold and say yes to those things that scare them. The best way I know how to demonstrate this is by simply just doing it. Death taught me what is at stake.


But (yes, there is a but, and I hate admitting it), I have not successfully embraced this mindset in dating. It took some time after Don’s death to have the courage to start dating again and what emerged were old stories, fears and beliefs about myself that got in my way of vulnerability and true intimacy. It resulted in choosing someone who affirmed those beliefs and fears, resulting in a failed relationship and deep frustration.


Given that I am well aware of what is at stake, my new quest is to date with the end in mind. And, I am not searching for "the one." For me, this is a ridiculous notion. Instead, my focus is on becoming the one who will attract this mate and experience a deep and lasting connection.


What does this all mean? It comes down to creating a clear vision of this relationship from the perspective of death. I imagine myself fifty years from now (I will be in my mid 90') sitting with my love at the end of my life. Together we reminisce, share our journey, and honour the path we have walked together. I ponder who I am in this relationship. How did I express myself and honour my values? In what ways did I support my partner, and how was I supported? I ask what was essential in this relationship that I did not compromise on?


I journal this conversation and answer these questions, becoming clearer and more specific. This then guides my choices in the present and gives me confidence in what I am saying yes to and what I am saying no to. If I am feeling resonant and aligned, it is easy to say yes to a situation or a person. If there is dissonance, it is a sign to readjust or make a different choice.


So what have I come up with thus far? I desire long-lasting trust, commitment, loyalty, connection, risk, passion, adventure, and the joy of bearing witness to another person’s wondrous life and he of mine. I envision that I have developed strength in turning towards the other with courage, compassion, intimacy, forgiveness, resilience and love. If fear emerges, it is managed with kindness and patience. The true magic is that I experience myself as fully present, vulnerable, and facing the other person, despite sometimes not wanting to. In the end, my desire to have been deeply loved and loved deeply is fulfilled.


Now a vision without action is only a dream, and hence I recognize that I have no choice but to put myself out there and say "hello," whether it be on a dating site, at the tennis court, at my next course or the grocery store. In holding this vision close to my heart combined with inspired and intentional actions, the chance of finding a lasting relationship will be much greater. Maybe I will find someone to love, and perhaps I won’t, but with the vision of the end in mind guiding me, I am more likely to show up as a bold, loving woman rather than my fearful self. And, in the end, this is the most crucial thing; anything less is not acceptable; too much is at stake.


So wish me well on my love journey. Keep your eye out for updates, and let the adventure begin!


(p.s. Oh! And if you know of someone or you find this intriguing, maybe we could connect to chat and possibly go on a date!)

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