Young Men Need a Miracle: The Mystery of Modern Dating

Thomas Sowell, one of my personal favorite intellectuals, has an important insight about wealth.

“There’s no mysterious explanation as to why some people are poor. The question is why have some people gotten prosperous.”

In other words, explaining failure isn’t that interesting or useful. Explaining success is where the money is.

While interviewing Rob Henderson a few weeks ago, I came up with my own riff on the quote. It went something like:

“There’s no mysterious explanation as to why some young men are incels. The question is how do some young men get laid at all.”

Okay, that’s a crass way to put it. The older I get, the deeper my Catholic roots grow, so I’m not exactly endorsing casual sex… but I think you get what I mean.

Think about what courtship actually requires: courage, tolerance for uncertainty, resilience through embarrassment. It’s kind of amazing that any young man ever succeeds.

Over the weekend, this video went viral on X once again.

From 1930 to 2024, couples went from meeting overwhelmingly through family, school, friends, neighbors, and church, to meeting online over 60% of the time. I guess that’s not that shocking in 2026, but what has the effect been?

In our conversation, Rob mentioned a statistic that’s really telling.

“About half of men between the ages of 18 and 25 have never asked a woman out on a date.”

Not “never had a girlfriend.”

Not “never had sex.”

They’ve never even asked.

In modern American culture, asking someone out is the first step in even having a shot at starting a family. We don’t do arranged marriages, at least not for over a century, so there’s no other option. Now we’re talking about a huge portion of young men who simply never take that first step.

Rob made another observation that stuck with me.

“Among young guys, it seems like being an incel is not really that stigmatized anymore. What’s stigmatized is caring.”

It’s not just that some young men aren’t going out and taking risks. It’s that the pressure to get a girlfriend has disappeared altogether. You’re even discouraged from caring that you’re single.

When I was growing up, if you didn’t have a girlfriend, it bothered you. I can remember this feeling quite clearly.

In middle school, and especially high school, if you didn’t have a girlfriend, you wanted a girlfriend. If you couldn’t find anybody in your school that liked you enough, it sucked. You’d think, “What’s wrong with me? Why doesn’t anybody like me?”

You liked hanging out with your buddies, so everything was okay for a while… and then one of them got a girlfriend. The pressure was on.

That experience was daunting, but at least it seemed like everyone was trying. Some were more successful than others, but we were all in the same boat.

Rob shared a story that captured this perfectly.

His best friend in high school had a crush on this girl in their class. Rob also knew from her friends that she felt the same way. Everyone was rooting for them, but no one had made a move yet. It was an open secret.

Eventually, his friend finally went in to pop the question. Having eavesdropped from about a dozen feet away, Rob retold the awkward conversation:

Him: “Hey, so you know, our friends have been talking and like, you know, I guess I should just tell you… I can’t believe how hard this is for me… I want to ask you something.”

Her: “It’s okay, you can ask.”

Him: “I don’t know if I can… Will you go out with me?”

Her: “Yeah.”

And that was with everything already in place. His entire social circle was coordinating the situation like a diplomatic negotiation and the outcome was basically guaranteed, but he still was terrified.

Courtship has always been hard. As Rob and I reflected on our adolescent memories, it’s a fragile balance that miraculously happens to work out sometimes… which brings us back to that video.

If you go back far enough, or just look at more traditional societies around the world today, teens and young adults aren’t expected to figure out relationships on their own. Arranged marriage has its own problems, so I’m not suggesting that we turn back the clock, but today’s norms clearly aren’t working.

In 1930, family and local community dominated everyone’s lives, so that’s how couples came together. You’d either end up with someone you’d known your whole life, or someone that someone you’d known your whole life had known their whole life.

Today’s online-dating-dominated landscape is about as far from that as you can imagine. It’s a largely impersonal, algorithm-driven guessing game.

Add in the escapism of online pornography and the rational, if sometimes exaggerated, worries of our post-#MeToo culture, and you have the perfect recipe for perpetually single young adults.

This problem won’t be solved by crossing our fingers and hoping for the best. We need to be proactive about this with our kids. The instincts that once pushed teens and young adults to get together just aren’t working.

Upside, fewer teen pregnancies. Downside, fewer pregnancies across the board.

These days, “the talk” has to be about more than just clinical biology and stern warnings. It needs to include something previous generations didn’t need to explain quite so explicitly: that finding a spouse and building a family is the central project of adult life.