I've been thinking about friendship a lot lately, which is probably the most millennial sentence I've ever written. And not about optimizing my social circle or implementing some productivity hack for human connection. I've been contemplating the messy stuff: the peculiar grief of male friendship and why we're all so spectacularly bad at it.
Three things converged recently that made me realize I wanted to write about this. First, I finished Season Four of The Bear, watching the series protagonist Carmy and his maddening refusal to grow—it takes him nearly thirty-eight episodes to figure out that pushing people away doesn't work, and even then he's still sulking. Specifically, there's a moment in episode two of S4 titled “Component Parts” where his cousin and sparring partner Richie, exasperated, asks him: "Can I lock up or is that gonna interrupt your mopin'?" It's the perfect encapsulation of how exhausting it is to be around someone who won't do the work of connection. Second, I read "Tech Companies Have Created a Loneliness Doom Loop," a brutal New York Times opinion piece by Samantha Rose Hill about how AI companions are being marketed to lonely people as a cure for isolation—spoiler alert: they're making it worse. And third, a reaction that surprised me: I heard through a mutual friend that someone I used to be close with was in town, having dinner with people I know, and for a split second, I felt a deep pang of jealousy and woundedness.
This shouldn't have bothered me, and in truth, the sensation lasted a millisecond. This old friend and I haven't spoken much in over fifteen years. But if I'm being honest with myself, it did bother me, in a way that made me wonder about how we process relationships and whether we’re actually as evolved as we pretend to be.
Let me tell you about this friendship. We were close in our early twenties, the kind of close where you assume this person will be in your life forever, where you talk with uncommon regularity and unguarded honesty. We shared that easy intimacy that feels impossible to replicate as an adult, partly because you're too self-aware now to be that unselfconscious.
And then, one day, it just... ended. No big fight, no dramatic falling out, just a gradual fade that became a permanent silence. Like a TV show that gets canceled without a proper finale. You're left with all these unresolved plot threads and no idea what the writers were thinking. Like My So Called Life but my so called life.
I'd spent a lot of time in the past trying to figure out what went wrong. I was a coroner dissecting the corpse. Was it something I said? Something I didn't say? Did I miss some crucial social cue that signaled the friendship had an expiration date? The not knowing permeated in my brain like an irrepressible stink and I wondered what happened, like emotional archaeologists trying to piece together a civilization that mysteriously vanished, the lost kingdom of Bromantis.
This is part of the work I've been doing for years now; trying to rewire my brain to be less sensitive about these oversights and perceived slights. It's like being your own therapist, constantly checking whether you're reading too much into social situations, whether someone's lack of response means they're busy or they're done with you. Part of being an active participant in adult socialization means accepting that not every interaction carries deep meaning, that people have lives and priorities that don't revolve around maintaining perfect communication with you. But knowing this intellectually and feeling it emotionally are two very different things.
As a child raised in a small community, my pool of friendship choices was limited, so I didn't always end up in the best relationships. What we now call "toxic" was just "boys will be boys" or "character building," they said. This left me with a particular approach: I'm constantly assessing my friendships in real time, making sure they're "good for me," working overtime to maintain them. I'm that guy who remembers birthdays, initiates plans, checks in when people are going through rough patches. It's work, but it's also how I've built relationships that actually last. Without that effort, without someone willing to remember and reach out and show up, friendships just... evaporate. And the alternative is how you end up with a contact list full of strangers, and an iPhone full of phantoms.
This is where the cultural conversation around male loneliness gets particularly infuriating, because most of the proposed solutions are either technological Band-Aids or social shortcuts that completely miss the point.
Take Yang-Yi Goh's recent GQ piece, "The Cure to Male Loneliness Is Befriending Your Wife's Friends' Husbands” in which he suggests that the solution is called "homies-in-law" (did you just gag a little too?). They’re essentially connection by convenience. But this approach is weak, effortless, and fundamentally lame. Goh writes, "I understand that my cure to male loneliness—finding the love of your life, lucking out when said love's friends are supremely chill, and then becoming friends with those friends' also-chill spouses—isn't exactly an easy-to-replicate, one-size-fits-all solution."
His "solution" requires having a wife with a robust social circle full of compatible couples, which immediately excludes single men, divorced men, men whose partners aren't naturally social, or anyone who's moved to a new city without the luxury of an existing social infrastructure. But more than that, it's a cop-out disguised as wisdom. It's saying that male friendship is so difficult and fraught that we should outsource the hard work of building genuine connections to our romantic partners.
[Incidentally, Goh’s proposal isn’t all that original. John Mulaney captured this perfectly in a 2020 SNL monologue: "My dad has no friends, and your dad has no friends. If you think your dad has friends, you're wrong. Your mom has friends, and they have husbands. Those are not your dad's friends."]
The AI companion route is even more insidious. Tech companies are literally monetizing loneliness, promising relief through digital relationships that offer all the comfort of human connection without any of the messy complications. As Rose Hill in that Times piece pointed out, these apps don't cure loneliness. They create a "loneliness loop" where users become increasingly isolated from real human interaction while believing they're addressing their need for connection. The author notes how "Social media, dating apps and A.I. companions won't alleviate loneliness; they will make it worse by giving people a way to avoid their aloneness."
Both approaches share the same fundamental flaw: they're designed to avoid the vulnerability that makes real friendship both terrifying and meaningful. They promise connection without risk, intimacy without the possibility of rejection, relationship without the emotional labor that makes human bonds worthwhile. But friendship without vulnerability isn't friendship—it's serving a life sentence of small talk. So, what do you think of this weather? Hot out there, eh?
In a recent New Yorker profile titled "Should Men Even Have Friends?" about the new film Friendship (starring Paul Rudd and Tim Robinson), director Andrew DeYoung reveals the movie was therapeutic for him. A few years ago, after befriending a colleague, he reached out to hang out, and the guy blew him off. “I saw myself kind of spinning out,” DeYoung said. Once he got a grip, he wrote a screenplay inspired by the experience. A failed attempt at establishing a bromance can be so painful it requires a feature-length film to excise the pain.
Austrian-Israeli philosopher Martin Buber's book I-Thou, originally titled Ich und Du for the real Buliebers, offers a framework for understanding why this matters. Buber argued that we relate to the world in two fundamental ways: I-It and I-Thou. In I-It relationships, we treat people as objects—to be used, studied, categorized, or experienced (see; LinkedIn). This is how most digital communication works: we read a friend's text and mentally slot them into "needy today" or "being dramatic again." Chances are I’ve been on the receiving end of those designations.
But I-Thou encounters are different. Both people are fully present to one another—not as roles or functions, but as whole, sacred beings. It's not about exchanging information; it's about a shared moment of recognition, where both are changed by the encounter. Buber insists that true I-Thou relationships can only occur in real time, in the living present, because they require mutual presence, body language, vulnerability, and undivided attention.
Think of a moment where someone really looked you in the eyes, listened without distraction, and responded not with advice or a meme, but with presence. That's I-Thou. It doesn't scale. But it changes us.
When you grab coffee with a friend and lose track of time in conversation, or when you sit quietly next to someone in shared grief or joy, that's not just nice. That's existence at its highest vibration, according to Buber. "All real living is meeting," he writes. We don't just have relationships; we are our relationships.
Male friendship is not supposed to be easy. The difficulty isn't a bug. It's a feature. The vulnerability required to maintain adult friendship is staggering, and it should be. You're asking someone to invest their limited time and emotional energy in you, to show up consistently, to navigate your baggage while you navigate theirs. All aboard the USS Friendship.
I've made some incredible friends later in life, people I consider among the best relationships I've ever had. These friendships feel like minor miracles, not because they happened easily, but because they required both of us to show up authentically, repeatedly, even when it was inconvenient or uncomfortable. There's this common misconception that because friendship was easy when we were kids, it should be easy now. But childhood friendship was circumstantial—we were thrown together by geography, forced proximity, shared activities. Adult friendship is intentional, which makes it both more precious and more fragile.
Case in point: I have a friend I now talk to several times a week, but we met in 2007. It's taken nearly two decades of investment for us to reach this level of closeness. But it was so worth it. I speak to another friend on the phone nearly every day despite being 2,700 miles apart. I probably know what he had for breakfast.
But despite what culture tells us about male independence—despite heroizing troubled protagonists like Carmy—we're not built to be lone wolves. The mythology of male independence is a construct. Men crave connection just as much as anyone else. But we've been trained to suppress that need, to treat vulnerability as weakness, to compete rather than connect. The result is a generation of men who are lonely as hell but don't have the vocabulary to talk about it.
Male loneliness isn't solved by AI companions or social shortcuts. It's solved by accepting that meaningful connection requires showing up, messily, vulnerably, and imperfectly. It means reaching out to that friend you've been meaning to text, even if you feel like you're always the one initiating. It means having difficult conversations instead of letting relationships fade into silence. It means accepting that some friendships will end badly, some will fade naturally, and some will haunt you for years.
I’ll probably always lament the friendship I lost twenty years ago, not because it was perfect, but because it represents my younger self's capacity for easy intimacy, for assuming that good relationships would naturally persist without constant maintenance. I can't get that friendship back, but I can learn from its loss. I can show up better for the friends I have now. I can make time for them, even when my post-Covid lockdown brain sneakily yearns for isolation.
Because in the end, friendship is making time for people who matter, even when it's inconvenient, even when you're not sure they'll reciprocate, even when the conversation might just be fine instead of transcendent. It's the choice to keep choosing each other, over and over again, until one day you realize you're not lonely anymore. Not because you've found the perfect solution, but because you've done the work of being present. The friendship I lost twenty years ago taught me that. The ones I have now prove it.