Middle Aged Men: Online Dating at Life's Crossroads

Let’s face it, dating is hard. For anyone at any age.

But for those of us men who have reached…shall we say, “a certain age” it poses a unique set of challenges. And there is evidence to suggest that the obstacles discourage men.

A survey by the Pew Research Center done earlier in 2020 shows that only 19% of men between the ages of 50-64 have even tried an online dating app. That figure will include everyone who has casually created a profile at the behest of their kids and then never bothered to check the account after that. If we narrow it down to men who have actually been in a relationship with a woman they met online, the result drops all the way to 7%.

Most people, both men, and women, that are on the dating market in this age bracket have likely been married before and may have children. If kids are still living at home, they naturally take priority before any sort of dating relationship. Long-distance relationships may be off the table if there are restrictions on either spouse moving, to say nothing of the need to consider the kids’ emotional stability if mom or dad is on a plane regularly doing the long-distance thing.

Those aren’t obstacles to be overcome, they are realities to be lived with.

But what of the man who has never married, or has been, but doesn’t have kids?

I re-entered the dating market in my mid-40s after a failed first marriage. We didn’t have kids. And while it was a blessing that children didn’t have to impacted by a divorce, I was also facing the reality that life hadn’t exactly gone as I had hoped. I used to envision a nice Irish Catholic family with 4-5 kids. Now that was crashing down around me. What could I do?

People assured me that I could easily look for a woman in her mid-to-late 30s. And that’s true. There isn’t anything creepy about a 45-year-old dating a 36-year-old and the opportunity to start a family would soon be there. I was absolutely open to that idea. But there was something gnawing at me.

What if having a family wasn’t God’s will for me? What if that was the reason for all the starts and stops, in both previous dating pursuits and then the failed first marriage itself? The family is a beautiful thing—indeed, the Church teaches that it’s sacred. But nothing, no matter how good, can be run on self-will. As a nun I used to regularly visit at a bookstore in Pittsburgh would tell me, “We’re here for one reason—to learn to love God.” She would add that if being married and having kids was necessary to help me do that, it would happen.

But what if that wasn’t the best way to learn to love Him?

Furthermore, I had been a part of the CatholicMatch community a long time, from the message forums to get-togethers with a large number of fellow CMers. I had seen men try to force their will on things. In some rare instances, it bordered on a theatre of the absurd, with men aged 60-plus chasing girls young enough to be their daughter. Most of the time, it was just a sad pursuit where the man overlooked perfectly nice women his own age in order to chase a dream that was dead.

Undoubtedly, there’s a lot of women reading this article and nodding their head in agreement. But in defense of “that guy”, keep in mind that something very profound has to happen within his soul. It’s the death of a dream—one that was perfectly moral and rooted in Catholic teaching. It’s a death that’s painful and doesn’t happen by flipping a switch.

And there’s also this reality, one I had to navigate—while accepting that God may not be calling you to have a family, He also…well, maybe He still is. It could be anything from connecting with that woman who’s ten years younger to marrying a woman who has children from a previous marriage. Everything is completely up in the air and that can be an even more difficult and painful place to live than the one where your dream dies. In the latter, at least you have some certainty.

The takeaway from all this is that everything simply must start with a strong prayer life.

Specifically, the rosary, the weapon by which we overcome all obstacles, and getting our guardian angel involved. This is true for everyone in all circumstances, but the urgency is more apparent when the possible paths God might lead you down are so numerous. The Blessed Mother will help. Your guardian angel will point out the path—probably not all at once, but one step at a time. Our responsibility is to surrender our will to accept whatever the outcome is.

For me, the outcome was that I married a woman who is my own age, with a lively faith, a great sense of humor and for whom my personality ideally meshes with. In our first year of marriage we were put to the test of having to spend every waking hour around each other under the COVID-19 quarantine. And all is well. We are exceptionally blessed.

So if you’re a guy looking to start anew in middle age, take heart. Put up a profile and don’t be afraid to use honest photos—not something from your college yearbook. Cast a wide net and remain open to all possibilities. And let God match you with the right person.