There is a particular kind of grief that comes with divorce later in life. You do not just mourn the relationship. You mourn time lost, momentum lost, the version of yourself lost, and joy lost. Life kept going, and so did I. I rode my bike. I went to the gym. I showed up for work. Slowly and intentionally, I began rebuilding—not the life I had planned, but a life that was genuinely mine.
I no longer see those years only as the season when everything fell apart. They were also the years when I learned that a life can be dismantled without being finished. I could not have known it then, but I was being prepared for a chapter I had never imagined—and for a love I was not yet ready to believe was possible.
Healing rarely happens all at once. It begins with small decisions—choosing hope over bitterness, curiosity over fear, and believing that life may still have good surprises waiting. I was no longer going to live my life lonely, void of laughter and joy.
Before my divorce from Cindy, online dating had never crossed my mind. Not once. It wasn’t part of my world, my wiring, or my imagination. Relationships, for better or worse, had always happened organically—through work, mutual friends, or shared life circumstances. Apps weren’t part of that story. Until suddenly, they were. Enter Match.com.
I found myself staring at the Match.com homepage, feeling a strange mix of curiosity, vulnerability, and readiness. I probably didn’t wait very long. But it also felt right. I wasn’t trying to escape anything. I wasn’t trying to numb pain or replace loss. I was simply stepping forward—intentionally—into whatever was next. And what I found surprised me.
What struck me almost immediately was how genuine many of the women on Match seemed to be. There was far less game-playing than I had expected. Many were direct. Thoughtful. Honest. They weren’t looking to impress so much as to connect. They were, quite literally, looking for a match.
That alone felt refreshing. Then I did something crazy. I bought two tickets for all the theater and musical events that I was interested in going to for the rest of the year. Hundreds of dollars for the Orpheum, the Dakota, Orchestra Hall. In the past decades, I was the guy who stayed home with the dogs while my wife and son went on vacations. Dutiful. Practical. Boring. I did not know who I would be going with, but I knew at least I would be there. I was taking back control of my life, and I liked where it was now going.
I took my time setting up my profile. I didn’t want it to be clever or flashy. I wanted it to be true. I had many hours to think in that tiny bedroom of the rental unit and then the studio apartment. To set about what needed to be released from my life and what needed to be welcomed in. I thought about growth—about what the divorce had taught me, the ways I had contributed to the breakdown of the marriage, and the areas of my life I was actively working on. I thought about faith and God and how more of that might bring some more of other things I wanted for my life. As my mind was changing, so was my body. Biking 100 miles per week was my solace, and with that came a glowing tan, tighter abs, and a feeling of health and vitality. I started lifting with more regularity. Gone were the old drab wardrobe of grays, browns, and baggy. I felt good in my skin. It felt good to finally feel good.
I wasn’t interested in presenting a finished product. I was presenting a man still becoming. I chose photos carefully—not to hide anything, not to enhance anything artificially, but to reflect reality. No decade-old photos. No illusions.
If someone was interested, I wanted them interested in me, not a version of me that didn’t exist anymore. One of the first women I went out with was Susan. We had a wonderful time meeting near a park in Minneapolis for drinks. When we finished the date, she shared that I didn’t look anything like my photos. I was surprised and asked whether she felt like I misrepresented myself. She laughed and said I looked much better than the photos on my profile and suggested I find better pictures to post. What an ego boost! I certainly needed that given where I was in my life. But I took her advice to heart and started to see the new me and help others see that too.
I was in my late 50s, and I was intentionally looking for women who had lived enough life to share similar experiences. I wanted common ground. Shared context. A sense that we had both been through things, learned from them, and were standing on the other side a little wiser. If someone had children, I assumed they would likely be older or already out of the house—and honestly, that mattered to me. I wasn’t interested in starting over as a parent to teenagers. That season of life had passed. It was about clarity. And clarity, it turns out, is attractive.
It didn’t take long before interest started coming in. Messages. Likes. Profile views. Conversations. And then… dates. A lot of dates. Looking back, I probably overdid it that first month by a lot. I’d guess I went on 30 or more first dates in those early weeks. Occasionally, that meant coffee with one person, lunch with another, and drinks with someone else—all in the same day. That wasn’t the norm, but it happened more than once. When you say it out loud, it sounds exhausting. Oddly enough, it wasn’t.
It was light. Fun. Low-pressure. No heavy expectations. Most dates were simply coffee, a walk, a meal, or a drink. A conversation. An exchange of stories. A shared hour or two. And then, often, a polite goodbye. Many of those dates were one-and-done. No spark. No chemistry. No obvious “next.” But that didn’t mean they were bad experiences. In fact, most weren’t.
Some women were genuinely interesting. Intelligent. Kind. Engaging. We laughed. We talked easily. But something essential was missing—not something you could point to or explain, just a quiet knowing that this wasn’t it. And that was okay. What I didn’t do—and this matters—was rush into anything romantic. I didn’t get physically or emotionally entangled. I stayed present, curious, and respectful, but I kept healthy boundaries. That wasn’t accidental. It was intentional. I had learned enough by then to know that clarity is lost quickly when emotions run ahead of wisdom.
Of course, not every experience was seamless. Some profiles were beautifully done—thoughtful writing, recent photos, honesty that came through clearly. Others… not so much. A few were obvious attempts to hide reality: old photos, cropped angles, vague descriptions. And yes, there were a couple of moments where meeting in person came with a surprise that required a quiet internal recalibration. But even that became part of the learning curve. People are human. Fear shows up in profiles. Hope does too.
Overall, my experience with Match was positive. I met people I never would have met otherwise—people whose paths would never have crossed mine in daily life. I worked in a male-dominated field. My routines don’t naturally place me in spaces where I’d meet many women organically. Match changed that. But it didn’t change the fundamentals.
The process itself became familiar: messaging would lead to texting, texting to phone calls, phone calls to a physical meeting. We’d usually agree ahead of time to a set duration. Thirty minutes. An hour. No pressure. No awkwardness. If it was good, it could continue. If it wasn’t, it could end gracefully. That simple boundary alone made everything feel safer and more humane.
Nobody felt trapped. That mattered more than I realized at the time.
And then—quietly, unexpectedly—it all stopped.
I met Pam in late July. From the very beginning, it was different. Effortless. Natural. Clear. There was no ambiguity, no wondering, no internal debate. I knew almost immediately that my time on Match was over. I didn’t hedge. I didn’t keep options open. I didn’t schedule more dates “just in case.” I simply stepped off the platform. And that was that.
Canceling Match.com was far harder than joining it. Finding the cancellation option felt like navigating a maze—layers of menus, confirmations, warnings, and subtle nudges designed to keep you subscribed. It became a running joke among people I met: “Match is great… if you can ever escape it.”
Looking back, Match.com for me was about rediscovering hope. It reminded me that even after disappointment, new beginnings remain possible. Online dating introduced me to people I would never have met otherwise, but it still required honesty, discernment, and patience to navigate well. What began as a simple Match.com profile ultimately led me to the love of my life, my true partner, and the greatest blessing to come from that season of my journey. I would find out later that she had gone through all the eligible men that met her "requirements" and made her profile only visible to a handful of men. I was one of those lucky men.
Among dozens of first conversations and first dates was one woman who quietly changed everything.