Learning to Belong

What my guests on ILLUMENATE taught me about friendship

For most of my life, close male friendship felt like something other men had figured out and I hadn’t. I grew up building deep, lasting relationships almost exclusively with women — the people with whom I felt safe enough to share myself. My connections with men stayed functional, polite, even pleasant, but never deep. I didn’t know how to change that. I also didn’t know that I needed to.

It wasn’t until my forties that I began to feel something missing. I realized I wanted male friendships not as accessories to my life but as essential components of it. Those early gaps — a lack of models, a lack of language, a lack of emotional space — became the reason I’m now fascinated by how men connect, why they often don’t, and what changes when they finally do.

That curiosity helped shape the conversations on ILLUMENATE. I asked every guest a version of the same question: What role does male friendship play in your life? Their answers painted a textured, hopeful picture of what meaningful connection between men can look like and the places where we still struggle.

Triangulation and the Quiet Loneliness of Men

Jason Lange gave me the concept that has reframed nearly everything I think about male friendship. “Most men by default connect through what I call triangulation,” he said, explaining that men tend to bond by placing their attention on a third point — sports, hunting, cars, fixing something — rather than on each other. “We connect by putting our attention on a third thing… but it doesn’t necessarily hit the connection juice that a lot of us need.”

Jason described the outcome all too clearly: “So many men can go out, spend a weekend with their bros, have a nice dinner, and come back and feel lonely,” because “you’re not supposed to talk about what’s happening inside.”

Loneliness beneath togetherness. That resonated.

But Jason wasn’t alone. Brent Diggs admitted that male friendship is “very important, but it’s also a struggle for me,” noting how easy it is for men to drift apart unless someone (often a woman) steps in to orchestrate connection. “Without them… I tend to lose touch.”

Even Prince Robertson described becoming selective to the point of precision: “I can honestly count on one hand [men] that I can contact and be vulnerable with on a different level.”

These men weren’t saying they lacked relationships. They were saying they lacked a certain quality of relationship: the kind in which you can reveal yourself without having to defend yourself. The kind most men were never taught how to cultivate.

What Happens When Men Turn Toward Each Other

If triangulation explains why male friendship often stays shallow, these conversations show what becomes possible when men choose something deeper.

Jason described his men’s groups as beyond friendship, relationships in which men show up for each other at levels usually reserved for family. When he learned his newborn daughter was deaf, it was his group of men who “held me as I just wailed… These are the men I go to when I can’t hold it anymore.”

He contrasted that with the common cultural script that tells men to tough it out alone. “Most of us men have been honestly just fed a spoonful of horse shit,” he said. “You don’t have to suffer alone.”

Brian Brauer echoed a different but equally powerful thread: the enduring ease of long-standing male relationships. “Some friendships take a lot of work to get started,” he said, “but once you’ve got it going, it keeps itself moving.” His Boy Scout friends are still the kind he can meet up with decades later and feel “like no time has passed.”

Mel Fenner spoke about brotherhood born of shared purpose. His fraternity brothers remain “like blood brothers to me” and created an infrastructure of belonging that feels both voluntary and enduring. Male friendship, for Mel, is “a sounding board… a group of gentlemen that I can confide in and know that they won’t judge.”

Even Brent — the first to admit his struggles with maintaining connection — described how meaningful it is when he and his male friends split off from their couples’ gatherings to talk about the things that matter.

And then there was my favorite thread across nearly all of these conversations: vulnerability as the entry point to belonging, not the cost.

Prince described vulnerability as a two-way exchange, not a performance of weakness: “It gives a snapshot of who I am and… helps me read that person” while creating shared accountability. “Now I know I have someone else that can hold me accountable whenever I get weak.”

That line stayed with me. Men often fear vulnerability because they imagine it will leave them exposed. But these men suggested the opposite: vulnerability is what gives strength structure. It is what lets support flow in both directions.

Common Threads: Belonging, Purpose, and Permission

As I listened across episodes, the patterns became unmistakable.

Men crave belonging and purpose. Jason named it directly: “[Men] want belonging and purpose… and when they feel neither, they become very open to manipulation.” It’s a difficult truth, but a clarifying one. Belonging isn’t a luxury; it’s a stabilizer.

Men need spaces where emotional expression is both allowed and expected. Over and over, guests spoke about places — men’s groups, fraternities, long friendships, teams, faith communities — where men are permitted to drop the armor. As Jason put it, men’s group is simply “what happens when we turn our attention on each other” and ask, “What’s going on in your life? What hurts?”

Men are hungry for accountability that doesn’t shame. Prince described accountability as a reciprocal gift. This is accountability not as correction but as accompaniment.

And perhaps most of all: men want connection that feels safe. As Mel said with understated clarity: “I know I won’t be judged. I know they’ll listen.”

In a culture that asks men to perform competence at all costs, these moments of genuine belonging are nothing short of radical.

Why This Matters to Me — and Why It Matters Now

When I began this podcast, I was driven partly by confusion and partly by concern. “What is with men in this country?” I found myself asking again and again. The more I explored, the more I came to believe that so much of the turmoil we’re seeing stems from a lack of belonging — a vacuum easily filled by anger, extremism, or numbness when not filled by community .

Talking with these men didn’t just give me answers. It gave me something I didn’t expect: a sense of hope.

I saw men who are breaking cycles, men who are choosing connection over competition, men who are modeling healthier masculinity not as theory but as lived practice. Men who are learning, sometimes awkwardly and sometimes beautifully, how to turn toward each other instead of away.

It also made me grateful for the male friendships I’ve finally built in my own life — friendships shaped not by triangulation but by presence.

The kind of friendship I used to think was for other men.

The kind of belonging that should exist for all of us.

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