Is Dating Still Fun? On Men’s Loneliness

Loneliness, Love, and Friendship: Notes from Our First “What About Men?” Discussion — written on the basis of a recorded conversation with Patrick, Robin, Jack, and Julian

I launched “What About Men?” with a simple aim: to make a space where we could read across political lines and speak plainly about what’s happening to men’s lives, without the performative rancor that often surrounds this topic. For our first session, I chose loneliness — both in romance and in friendship — because the social rules seem to be shifting under our feet. Many of us sense that something is off, yet the diagnoses we hear are often one-sided: it’s the apps, or it’s the politics, or it’s the economy, or it’s men, or it’s women. I suspected the truth would be messier and more human. It is.

You can watch the full recording of the conversation here:

www.youtube.com/watch?v=vslMn6JfFro

Our group for this opening session included me (Berlin), Patrick (a mentor and organizer in men’s personal development), Robin (who has spent time in sharing circles and multiple intentional communities), Jack (an American who has worked on male-gender issues since the early 1980s and married at sixty), and Julian (also in Berlin, interested in how frequent moves affect connection).

We began by flipping a coin to decide which pair of short opinion pieces to read first — turned out to be the more conservative one. Then we read, in silence, with cameras on, like a class you wish your school had offered. After that we talked. What follows is my reflection on that conversation. When I attribute a point to someone else, it’s what they said; when I speak in the first person, it’s my own synthesis.

Fun for whom?

Jack put down a strong marker early: dating, in his experience, is not fun anymore. He remembers the 1960s and 70s as lighter, more spontaneous, less tense. Today the stakes feel higher and the risks sharper: being misread, being accused, being treated harshly after a small misstep. He did not say this just as nostalgia; he dated well into his fifties before marrying at sixty and felt the shift even among older daters.

I take Jack’s feeling seriously. Whether or not you agree on the degree, many people do report a sense of walking on eggshells. My philosophical reflex, however, is to ask: fun for whom? For guys like us? Maybe. But if clearer norms around consent and boundaries reduce fear for women (and sometimes for men too), then the distribution of “fun” changes. A world with different ground rules can alter who feels at ease and who feels tense. The right question becomes: how do we design the environment so that safety and warmth coexist — so we aren’t trading delight for dread, or vice versa?

Agency, Technology, and the Scripts We Carry

Patrick welcomed the intergenerational angle and thanked Jack for being there. Younger men, he argued, often lack approachable elders and living role models. He also returned to the theme of agency. As a teenager, he changed his life — losing weight, building competence — mostly by trial and error. No guru, no magic. Just small steps, sometimes backward, more often forward. Many men, he suggested, are stuck at “zero to one,” and the first move is the hardest. I agree that agency matters — not as a denial of structure, but as a way to avoid learned helplessness. Action creates surface area for luck.

Robin, for his part, is frustrated — less with women or men than with the platforms themselves. He contrasted the ease of hosting couch-surfers years ago (men and women he didn’t know who stayed at his home) with today’s dating contexts, which feel tense, anxious, and sometimes hostile. His suspicion is that we have introduced a corrosive third party into romantic life: corporations whose incentives reward engagement over resolution. If the app “wins” when you keep swiping, it is no surprise that many people report feeling lonelier after heavy app use than before they logged on. This aligns with my own sense that technology has become a default middleman, and that the design of that middleman matters.

Jack raised another delicate point: we have grown comfortable with women voicing dating grievances and far less comfortable with men naming their own. He gave a simple example — who pays on a first date — and noted how assumptions about money can expand into assumptions about provision and status. Regardless of where you stand, it seems healthy to make room for men to speak about what feels unfair or lopsided without being pre-judged as hostile.

On roles, Patrick prefers complementarity to strict equality. He is at ease taking on more provider responsibility, in part because pregnancy and childcare introduce asymmetries that don’t vanish just because we no longer plough fields with our bodies. I pushed back, not to deny dependency during parenthood but to question the “naturalness” of fixed provider scripts in a world where many young women out-earn men and where competence is often cognitive and relational rather than muscular. Some women do not want a protector-provider dynamic; some men do not want to be evaluated primarily as providers. Scripts are teachable. They are historical. They can change.

Loneliness: More than Romance

Julian shifted the lens from roles to remedies. What if friendship is more decisive than partnership in curing loneliness? Can a man with deep friendships and an active community be non-lonely while single, and can a man with no friends feel crushing loneliness inside a relationship? This question landed. Many of us outsource too much of our social need to romantic partners — an impossible task when villages used to distribute that load across many shoulders.

Patrick offered a useful distinction: solitude is not the same as loneliness. He has learned to be fine alone, which makes him less desperate and more discerning when dating. In my own life, the capacity to be alone without spiraling has been one of the surest ways to choose well together; fear distorts judgment.

Community, Tribe, and Shared Life to Fight Loneliness

After a tea refill we read the second, more liberal set of texts, which inspired a discussion of friendship more directly. Robin, who has lived in multiple intentional rural communities, argued that shared life dissolves the masks that city friendships silently reward. If you meet people for three hours in a book club, they are performing, they’re not their authentic selves. But you cannot perform 24/7 when the same people see you before coffee. People see each other as they truly are. In those settings, trust accumulates because there is nowhere to hide. Competence and character are legible. Everyday contributions — chopping wood, cooking, cleaning — become grounds for attraction and respect.

Jack complicated the picture by sharing a painful family history. He grew up in a large but dysfunctional family; his father drank under the weight of provider expectations and seven children. Proximity by itself does not guarantee care. Community can crush as well as heal. To me, that doesn’t invalidate Robin’s love of communal life; it clarifies that the goodness of community depends on its quality, its norms, and its ability to distribute burdens fairly.

We explored whether authenticity is really impossible in cities. Patrick suggested it’s still a choice; he resists corporate masking and tries to be the same person everywhere. Julian agreed that deep friendships are possible in cities, but time density is the bottleneck: you cannot build thick trust with someone if you spend just an hour a week together. My take is that city and village sit on a spectrum, not a binary. You can design a city life that increases unmasked time — live near friends, build weekly rituals, invite colleagues into friendship, find “third places” that aren’t purely transactional. And you can hide in a rural idyll. The deeper issue is the habit of masking.

Systemic Versus Personal Causes of Loneliness

This led to the old question: is male loneliness primarily systemic or personal? Robin and Julian leaned systemic — platform design, urban living, the atomization that has dissolved tribes and large families. I argued that structure and agency are braided together. We should press for better design and different incentives; at the same time, no system can choose vulnerability on my behalf. The best solutions will be the ones we can practice tomorrow morning while we work for larger changes.

Meanwhile, Jack named a feeling many men recognize: being treated as “guilty before proven innocent,” especially in dating. I dislike that feeling too. But I also think the caution is not random; it is a response to real harm done by a minority of men. In small communities, reputation travels and acts as a guardrail; in anonymous cities and on apps, people protect themselves by assuming little and verifying slowly. Design that lets reputations be legible again — without creating new injustices — feels worth exploring.

Patrick then made a thoughtful case for masks — in specific situations. Firefighters, parents, and leaders sometimes need to project calm even when they do not feel calm. Jack agreed: composure can save lives. I don’t deny that. My worry is about residue. Emergency postures can calcify into personality; a mask worn all day forgets how to come off. What we need is situational composure without permanent concealment: the ability to be steady when it helps, and open when connection requires it.

Near the end we compared notes. Robin and I both sense that the American “rugged individualist” archetype remains stronger than in much of Europe; Jack links this to the frontier myth. Scripts differ by place. That matters because it proves these patterns are learned rather than fated.

So What Do We Do Next?

Talk is only useful if it changes what we do the next day. A few practical moves emerged or crystallized for me during the session:

1) Dealing with loneliness can’t be based on romantic relationships only. Build friendships on purpose — with men, women, everyone.

2) Take time back from screens and the impersonal city spaces. The systems we are embedded in determine our lives, and some systems do not naturally lead to connection.

3) Join small, regular, embodied communities. Men’s circles, faith groups, maker spaces, sports teams — anything with frequent contact and shared tasks.

4) Wearing a mask, while sometimes useful, is not a way to build connections. Seeing each other without a mask, as we are, is.

This requires a bit of vulnerability to show ourselves, which is not easy. Practice low-stakes vulnerability with friends before demanding high-stakes vulnerability on dates.

What stayed with me after we ended the call was how much wisdom appears when you remove the pressure to perform. Jack’s memories and cautions, Patrick’s emphasis on agency and composure, Robin’s argument for intentional community, and Julian’s insistence that friendship may matter more than partnership — each pulled me away from simple blame toward shared responsibility. If this project works, it will be because we keep making room for that mix: the structural and the personal, the philosophical and the practical, the voice that says “I’m lonely” and the hand that says “let’s meet on Thursday.”

Acknowledgments and Attributions

This essay is based on a recorded conversation. Jack contributed the idea that modern dating often feels high-stakes and risk-laden and offered context about the United States’ “rugged” scripts. Patrick emphasized personal agency, competence-building, and the place for situational composure; he prefers complementary roles in relationships. Robin focused on platform incentives and made the strongest case for intentional community as an antidote to isolation, contrasting city masks with rural transparency. Julian re-centered the value of friendship and asked whether partnership should be treated as a bonus rather than the sole cure for loneliness. Any errors of interpretation are mine.

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