
Essay 14 of 25
Ha!!
When it comes to heartbreak — Once?
Stop kidding!
Pull my other leg; it plays Jingle Bells.
Heartbreak and I are old friends. In a sea of some 30-odd relationships over the last 40 years, there is no “Once upon a time” for heartbreak; it’s all upon a time. But in every case, the “juice has been worth the squeeze.”
Let me tell you why. With the benefit of hindsight and wisdom, while the heartbreaks were emotionally and financially devastating, where I am at this [st]age of my ongoing development and evolution, the exquisite pain of each of them was necessary.
Because while the downsides of the relationships were steep, they were short-lived compared to the upsides of the years filled with good times and great love.
In the past year, I’ve had conversations with yet-to-be-married Millennials and Gen-Xers who have created a magical checklist of must-haves — born out of a self-described fear of getting into a relationship because they don’t want ever to get divorced.
Huh!?!
You might ask, “What does that look like?”
Fear has traumatized and reframed their entire attitude about love. Actually, I can’t say reframed because they never had a fearless frame of love and passion; thus, they approach love and relationships with the side-eye, “when is the other shoe going to fall?”
Some have stated this fear comes from personal experience as a child of divorced parents. As a pondering, how might his view of love and marriage be combined with looking at too many curated social media snapshots of beautiful relationships at moments in time? Perhaps too many romcoms have individuals living in a fantasy world of unrealistic expectations of what a relationship and a partner “should be.” Fairytales never show what the day-to-day and year-to-year relationships look like after “prince charming” and the “princess” ride off into the sunset.
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“You got to love the crust of a #@!*?@*~!
You can’t just love the white part of the bread.
You gotta love the crust, the crumbs, the tiny
crumbs at the bottom of the toaster.
That’s what the real #@!*?@*~! is.”
Chris Rock, Bigger & Blacker 1999
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Foundation
In 2022 my parents traveled to West Africa to celebrate their 60th wedding anniversary and renewed their vow in Ghana. They’ve known each other for 65 years, and both turned 80 before their anniversary. I had the pleasure of walking my mom to the altar and serving as my father’s best man.

Photo By iStockPhoto.com
In addition to talking for hours about business and everything under the sun, my pop and I often talk about relationships. In one of 2022 conversations, before heading to “the continent,” he said, “I just don’t know how you guys do it (multiple marriages); you know your grandfather (his father) was married five times to three women.” I know you’re thinking, “Huh?” “What?” Noodle on it for a minute. Anyway, in contrast, my mother’s parents were married north of 60 years till death did them part in when they were in their late 80s.
It looks like I’m on track to be more like my father’s father than my mother’s father, with whom I shared the same birthday half a century apart. Although I channeled my love for cooking from my mother’s father, he did all the cooking in the household, seemingly pretty radical in the 1940s. I guess I channeled my love of being in relationships from my father’s father. While I’m only two for two so far, I don’t plan to match or surpass that grandfather’s record of five marriages to three women. However, I’ll do a third round if my “Wow” (my combo pack woman) shows up (see “You Really Deserve Your Wow” — https://medium.com/hello-love/you-really-deserve-your-wow-9b02c39a9a77).
And if she doesn’t show up, that’s fine also. Because as I look back on my relationships, from dating to marriages, I’ve had a great run. Incredible women from all walks of life have loved me, and I’ve loved them. And we brought new life into this world.
I’m not one to give unsolicited advice anymore. I learned that lesson of something not to do back in 1987. Still, when I hear people with checklists of their magical thinking, “If I get all these things, I’ll never get divorced,” I think how they’re missing out on years of incredible love and passion, worrying about a negative future that may never come.
The 80/20 Rule
One of the lessons that my old man gave me decades ago was what he called his 80/20 rule.
Somewhere in the early 2000s he said, “Son, you’ll never get 100% of what you’re looking for in a partner. “If you’re lucky, you get 80%, and the other 20% will be things that you don’t like or wish were different, but you accept. Because trust and believe there will be 20% of things about you your partner will wish were different. Maybe years together, that 80% goes up to 90%, but you and your partner will never be 100%.”
Now with that, pop is practical, noting that within the 20%, there can’t be deal breakers. So everybody has to decide what their deal breakers are versus their “would like my partner to have” but could live without because friendship and love are the foundation.
So in a fantasy-induced social media fiction of snapshots of marital perfection where every image posted is perfectly curated, manicured, and vogue cover-ready, are too many potential couples leaving years of wondrous love off the table as they seek imitate the snapshot ideal?
Do people view a committed, loving bond through a lens of the 50/50 odds of a future marital failure and subsequent heartbreak in their imagination? All to avoid the ultimate “once upon a time of getting their heart broken because of divorce. Versus looking through the lens of love that brings joyous abandon.
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A Thought Experiment: Friends Forever or Chance a Marriage
Final thoughts, I recently shared a relationship thought experiment with a good generational friend and colleague who has been divorced once, with Gen-Z children, and is in the dating scene. I asked if he had two choices:
Choice One: To meet another great woman who is everything he wants, his “Wow,” and be guaranteed that they’d be great life-long friends but never be romantically coupled.
Choice Two: They could be romantically coupled and married; however, there is no guarantee their marriage and relationship would last — it could end in another divorce for him.
Which did he/we choose?
Without hesitation, he opted for Choice Two, as did I.
While he and I are from different worlds, realities and cultures, we know how beautiful love can be no matter how long it lasts.

Image by By iStockPhoto.com
He actually went deeper to reflect on his dating life of a three-year relationship and said, “Sure, break ups suck, but the pain doesn’t last; maybe a year.” So he said he’d take three years of a great loving relationship that ends and live with the pain for the one year. Then he’d do another three years on and one in pain. So for him, 3 to 1 would be a ratio of Love to Pain he’d do for the rest of his life. I agreed with him.
So if there are future heartbreaks, so what? Years of love eclipse them all.
This beautiful and intriguing insight was brought to life for me by a woman of certain st[age]. After reconnecting recently after 27 years, she said, “With all the wonderful women in your past, maybe you’ve had multiple mini “Wows.”

Illustration By iStockPhoto.com
So with her insight about multiple “Wows,” I’m down for my next great love, and should there be heartbreak at the end of another journey, while the downside can be steep, the upside is so easy for me to see. Because, in my case and my reality (mi rialiti), having the love and support of an incredible, sweet, kind woman who is also a fellow mission driven creator is unparalleled.
Accepting that relationships are precious and will only “last as long as they lasts” is very freeing.
Essay 14 of 25–12.25.2022
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This post was previously published on medium.com.
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Photo credit: iStockPhoto.com
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