There are certain chapters in life that you don’t plan for, don’t imagine, and certainly don’t rehearse. You just arrive there—sometimes suddenly, sometimes reluctantly—and do the best you can with what’s in front of you. For me, one of those unexpected chapters was Match.com. 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, church, or shared life circumstances. Apps weren’t part of that story.

Until suddenly, they were.

Not long after the divorce became official, 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. In hindsight, that’s obvious. 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—tentatively—into whatever was next. And what I found surprised me.

A Refreshing First Impression

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. 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 talked openly 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 wrote about faith, because it mattered to me, and because I was growing in it in a way that felt real, not performative.

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. What I looked like. What my life looked like. No decade-old photos. No clever angles. No illusions.

If someone was interested, I wanted them interested in me, not a version of me that didn’t exist anymore. Funny story. 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 a little surprised. Did she feel like I misrepresented myself? She said I looked much better than the photos on my profile and was pleasantly surprised when we met. She said to find better pictures to post. What an ego boost! I certainly needed that given where I was in my life.

Knowing What I Was Looking For

At that stage of life, I also knew what I wasn’t looking for. I was in my late 50s, and I was intentionally looking within what I’d call an appropriate age range—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, and I was at peace with that. This wasn’t about narrowing options. It was about clarity. And clarity, it turns out, is attractive.

A Flood of First Dates

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.

The Reality of Profiles

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.

From Messages to Meetings

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.

Then There Was Pam

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. More on Pam in a later post.

One Final Observation

There is one lingering memory that still makes me smile. 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.” In the end, I managed. And I didn’t look back.

Looking Back Now

That season of life taught me something important. Online dating didn’t change who I was. It simply widened the door. It 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.

Match wasn’t the answer. It was the context. The real work—self-awareness, growth, faith, boundaries, clarity—that all happened offline. And when the right person appeared, the noise faded quickly. That’s how you know. Some chapters are short. Some are loud. Some quietly do their job and then close. The Match.com chapter did exactly that. And I’m grateful it did.