I was 62 when I began dating again—41 years after my last first date.
My husband, Steve, and I met in graduate school and were married for 32 years. We built a partnership grounded in love, mutual respect and a life shaped by shared experiences and devotion. In 2020, after years of navigating his cancer journey together, Steve passed away.
Before he died, Steve made me promise I would create another chapter in my life. At the time, I couldn’t imagine what that would look like. Months later, I began to understand how profound that promise was—and what it would require of me. I knew I had to keep it, as a love letter to the life we built and to the woman I was becoming.
Dating again wasn’t about finding love. It was about defining and creating the next chapter of my life—and becoming the kind of partner I wanted to be.
In the year that followed Steve’s death, I sold a business, started growing a new one, deepened friendships, discovered a love for hiking, and spent long stretches alone. My identity had never been only my marriage—I had always had my own career and friendships—yet being in partnership for so long shaped how I moved through the world. I had never lived as a “party of one.” Those years alone both challenged and allowed me to define who I was as an individual.
During that time, I spent several months at my vacation home on the Big Island of Hawai‘i. Evidence of volcanic eruptions is everywhere—hardened lava, black rock and new growth emerging slowly from the earth. What looks like destruction eventually becomes renewal. I saw powerful parallels between that landscape and grief: Both are shaped by forces beyond our control, and both hold the possibility of what can emerge with time.
After the fifth anniversary of Steve’s passing, I felt ready for partnership again—and equally importantly, I knew I could be a great partner.
That’s the part people often skip. We talk about “putting yourself back out there” as if it’s just about bravery. But the deeper work isn’t returning to dating. It’s becoming clear about who you are, what matters to you and what kind of relationship you’re actually building toward.
As an entrepreneur—and yes, a Virgo—I approached dating with structure. I studied the platforms, wrote a profile focused on transparency and searchability, chose photos that reflected my real life, and created a spreadsheet to track conversations and patterns.
First objective: create a qualified pipeline. Only then could I evaluate connections more subjectively. What we think we want is theory. What we learn through experience is truth.
Over the next five months, I went on 32 first dates.
These weren’t random dates. I had a system: text first, then a phone call, then an in-person meeting. Coffee became my go-to—a defined timeline and an easy exit if needed.
Some people date casually. Some for companionship. Some for short-term connection. There’s no judgment in any of it. I only knew long-term partnership, and that clarity shaped how I screened and showed up.
Still, dating apps were a crash course in reality.
One man was articulate and funny in writing and on the phone, yet incredibly awkward in person and unable to hold a basic conversation. Another—successful, active and engaging—surprised me by proudly showing a video of his big-game hunting trip over lunch. Another suggested we test sexual chemistry over webcam before meeting in real life.
The list goes on.
After each date, I journaled—what felt aligned, what didn’t and what I was learning about myself.
Dating apps, I realized, are door openers, not diagnostic tools. They show a curated slice of someone—much like social media. The real person only emerges through time, conversation and shared experience.
The apps also create a powerful illusion: that something or someone better is always one swipe away. In reality, clarity and character matter far more than endless options.
And then came date No. 33.
Phil.
Our first coffee date flowed easily and felt grounded and real. Two days later we went for a hike, and the connection deepened naturally. Shortly after, I left for a pre-planned trip from California to Hawai‘i, and we stayed in touch through messages.
Through his words, I saw depth, humor, emotional intelligence and curiosity. For the first time, I felt I could simply be myself—and I recognized that I had changed too. I wasn’t the same woman I had been decades earlier.
Phil often says, “You be you, I’ll be me, and we’ll be just fine.” With him, there was ease instead of effort.
We built a foundation quickly—grounded in honesty, shared values, mutual respect and genuine admiration. Chemistry absolutely matters, and when held with trust and alignment, it becomes something rare and lasting.
Now, five months in, we’re both excited about the life we’re creating together and deeply grateful for the long road that brought us here.
I didn’t return to dating to find someone new.
I returned because I had already become someone new—and was ready for partnership from that place.
And that, I’ve learned, may be the real gift of second-chapter love: It doesn’t just bring the right person into your life. It reveals who you are when you finally choose with clarity.
Jayne Brodie is an entrepreneur based in Sausalito, California, creating a vibrant new chapter in life and love in her 60s.
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