On Deep Conversation & Connection in 2025

I'm tired of surface-level everything. You probably are too.

I sometimes eavesdrop on people’s conversations out in public. Last month, I took myself on a solo date at my favorite Italian restaurant and overheard two people, likely on a date, at the next table. Twenty minutes in, they were still cycling through the same loop: "How's work?" "Busy, you know." "Yeah, same." "Crazy weather lately." "Right?" They checked their phones between exchanges.

Later that week, a TikTok video from philosopher Jonny Thomson appeared on my feed. He argued that our lack of deep conversation has led to a disconnect not only with others but with ourselves. Coming across this video got me thinking about those two people trapped in conversational purgatory and this general agreement that we're losing the capacity to actually know each other, and in the process, we're losing touch with who we are.

This matters to me because if you know me, you know I value connection beyond the surface, getting straight into deep stuff rather than just talking about the weather cooling down because it’s now fall. I believe deep understanding unlocks everything, better collaboration, clearer thinking, genuine connection. But I'm watching those possibilities slip away, conversation by shallow conversation.

The perfect storm of disconnection

I don't think there's one villain here. It's more like a perfect storm of overlapping forces that have quietly restructured how we interact.

The technology piece is obvious but worth stating plainly. Pew Research Center published that 98% of Americans own a cellphone, with 91% owning smartphones, fundamentally altering how we structure our attention and social interactions. I notice it in myself, the reflexive phone check when conversation hits an uncomfortable pause, the mental calculus of whether to respond to a text mid-dinner, the way my attention fractures across three apps while someone's telling me about their week.

But the phone is just the delivery mechanism for something deeper: the media environment we're swimming in. Social media platforms are designed to maximize engagement through algorithms that prioritize extreme content, creating what researchers call "algorithmic amplification" of divisive material. We're consuming a steady diet of global catastrophe (e.g., climate collapse, political polarization, economic precarity) while simultaneously watching highlight reels of others' seemingly perfect lives. Passive social media consumption likely correlates with increased feelings of inadequacy and social comparison. How do you have a genuine conversation when your baseline is "the world is ending and everyone else has it figured out except me"?

Then there's the physical infrastructure of connection, or lack thereof. The concept of "third places," spaces that are neither home nor work where community naturally forms, has been in steady decline over the last two decades. Coffee shops now optimize for laptop warriors plugged into AirPods. Bookstores became Amazon. Community centers lost funding. The disappearance of these informal gathering spaces has contributed to increased social isolation, particularly in suburban and newly developed urban areas. Where exactly are we supposed to practice the art of conversation when every public space either costs money or demands you buy something to justify occupying it?

And here's where I might lose some people, but I'm going to say it anyway: some blame can go towards the skip generation above us…. not entirely, not maliciously, but there's something there. Gen X has been characterized as the "latchkey generation," raised during a period of rising divorce rates and dual-income household necessity, often with less parental supervision than previous generations. They grew up in the gap between community-oriented Boomers and digitally-native Millennials. This generation developed high levels of self-reliance and skepticism toward institutions, which influenced their parenting approaches. Many Gen X parents, understandably trying to give their kids what they didn't have, swung toward structured activities and constant supervision, but sometimes at the expense of teaching us how to just be with other people without an agenda.

Welcome to anomie

There's a term for this feeling: anomie. I saw it first in the Tik Tok video. French sociologist Émile Durkheim described anomie as a state of normlessness where societal rules and values have broken down, leading to feelings of isolation, despair, and lack of purpose. Durkheim observed this particularly during periods of rapid social change when traditional structures could no longer provide meaning or direction.

This might sound extreme, like I'm suggesting we're all wandering around in existential crisis. But look around. Young adults report record levels of loneliness, with nearly 60% of adults reporting feeling lonely frequently. We have more ways to "connect" than ever before and somehow feel more isolated. The rules that used to govern social interaction (e.g., you go to church, you join the bowling league, you chat with neighbors) have dissolved without clear replacements. What's the protocol now? Swipe right? Join a Discord? Hope someone plans something?

I don't think we're at full Durkheimian anomie, that's a bit dramatic, but I do think we're experiencing a milder version. The old scripts don't work, the new ones feel shallow, and we're all kinda improvising badly in the middle.

Are we f*cked?

No. I don't think so. And here's why.

1. Human nature is stubborn. Evolutionary psychologists have demonstrated that humans are fundamentally social creatures, with brain structures specifically evolved for complex social cognition and cooperation. The lack of connection probably activates the same brain regions as physical pain (check this study out looking into this), suggesting our need for community is neurologically hardwired. We're not going to suddenly evolve out of needing each other. The craving for genuine connection isn't going anywhere, it's just being temporarily suppressed by systems that make it harder to access.

2. We all know there's a problem. And ironically, social media, the thing that contributed to our isolation, is also the megaphone broadcasting that this is broken. The same algorithm that shows you unattainable lifestyles also serves up videos of philosophers explaining why you feel disconnected. We're having a collective conversation about the lack of conversation. That's the obvious step one.

3. Combine human nature and humans knowing there is a problem. I think we do see some evidence of correction happening. People are rediscovering solo dates, intentionally going to dinner alone, to museums alone, as a practice in being present. While it’s still solo, we’re pushing ourselves to go out (at least I am). Participation in interest-based communities and hobby groups has been rising among urban millennials and Gen Z, particularly for in-person activities. Event Brite released findings earlier this year on “fourth spaces, where online and offline worlds meets.” Book clubs (shameless plug: I host one), running groups, amateur sports leagues, crafting circles: there's a quiet renaissance of interest-based gathering happening that started out online.

A quick aside on pleasantries (and why they're necessary but not sufficient)

"How was your week?" "Good, busy." "What do you do?" "I work in tech." "Oh cool, what kind?" "AI stuff." "Interesting." "Yeah."

Here's the thing about pleasantries: they're a must, but they must fizzle out quickly. These "phatic expressions," talk that serves social bonding rather than information exchange, as a crucial element of relationship formation. They're not inherently bad. In fact, they serve a purpose: they establish basic safety, signal reciprocal interest, create breathing room for both people to adjust to the interaction. Think of pleasantries as the conversational equivalent of dynamic stretching before a run. Necessary, but not the point.

The problem is when we get stuck there. When "How are you?" gets answered with "Good, you?" on infinite loop. When we treat pleasantries as the destination rather than the on-ramp. I think we get stuck here often because of how technology, like texting, has influenced human communication: the ability to send a short, such low hanging fruit text to catch someone’s attention.

Pleasantries are a precursor to psychological safety, but they're necessary, though not sufficient. You can't skip them (well, you can, but it creates a quirky energy that I sometimes like to instigate). But you also can't stay there and expect connection to magically appear.

The hard work of psychological safety

In my opinion, psychological safety is the bedrock of deep conversation.

Pioneering research on psychological safety, particularly work by Harvard's Amy Edmondson, defines it as a shared belief that interpersonal risk-taking is safe within a given context. Establishing psychological safety typically requires consistent positive experiences over time, making it difficult to create quickly in new relationships. I think there’s also the component of vulnerability that’s required on both ends to establish this net.

And yet, some people seem to do it faster than others. Why?

I'd argue, and this is based on observation, not formal research (though some of my thoughts overlap with research findings), that rapid psychological safety requires a specific skill set:

• You have to be a god damn good listener. Not the "waiting for your turn to talk" kind. The kind where you're actively tracking what someone's saying, noticing what they're not saying, catching the slight hesitation before they answer a question. Active listening research demonstrates that effective listeners pick up on both verbal and non-verbal cues, creating space for deeper disclosure.

• You can't take things at face value. Someone says "work's fine" but their shoulders tense up? That's data. Someone mentions they "used to play piano" with a wistful tone? That's 100% a thread worth pulling.

• You need to be good at follow-ups. Research on relationship development suggests that consistent, repeated interactions are crucial for moving beyond acquaintanceship, with studies indicating it takes approximately 50 hours of interaction to move from acquaintance to casual friend, and 200 hours to close friend. One deep conversation doesn't create lasting connection. It's the second coffee, the follow-up text a week later referencing something they mentioned, the "hey, how'd that thing go?" That's where trust builds.

• And you have to be vulnerable yourself. I remember learning in my early human development classes at Vanderbilt about Brené Brown, who said that vulnerability in conversation creates reciprocal disclosure, with people matching the depth of personal sharing when others model it first. Not performative oversharing that makes everyone uncomfortable, but genuine acknowledgment of uncertainty, struggle, or complexity. From my view, "I'm not sure I handled that well" opens more doors than "Everything's great."

The example I like to share to exemplify this was when I was having coffee with someone I'd bump into at an external work function. About twenty minutes in, she mentioned she was thinking about leaving her company. I could've said "Oh yeah, the job market's tough" and moved on. Instead, I asked: "What would make you stay?" Pause. Then she told me about feeling invisible in meetings, about pitching ideas that got ignored until another colleague repeated them, about wondering if she was being too sensitive.

We chatted for two hours. I shared my own experience feeling like the one who stood out in certain rooms, the exhausting calculation of when to speak up. We exchanged how we felt in those situations, where our heads were at in those moments we probably won’t forget.

That doesn't happen without willingness to go there.

When do we even learn how to deeply converse?

The uncomfortable truth is that most of us don't get explicit instruction in deep conversation. We pick it up through observation, trial and error, sometimes luck. And because deep conversation requires psychological safety, that skill of making someone feel safe enough to share something real, we need repeated practice in environments where the stakes feel manageable.

So where does that practice actually happen?

Childhood is your first classroom, for better or worse. Developmental psychology tells us that children's social skills are heavily influenced by parental modeling and early attachment patterns. If your parents had meaningful conversations at the dinner table, processed emotions openly, asked follow-up questions about your day beyond "how was school?", you got a masterclass. If your parents were emotionally distant, conflict-avoidant, or simply exhausted (no judgment, parenting is hard), you might not have learned those skills.

Research also indicates concerning correlations between socioeconomic status and social-emotional development, with children from lower-income households often having fewer opportunities for complex social interaction due to factors like parental work schedules and resource constraints. It's an unfortunate reality that compounds other inequities. I can write a whole separate piece on this.

College, for those who go, becomes a forced melting pot. You're living with strangers, navigating first real relationships, encountering people from radically different backgrounds. My friends from abroad taught me more about deep conversation than any class. I remember sitting at Commons, the dining hall at Vanderbilt, freshman year with someone from China, someone from South America, and then someone from Texas (I was from New York City). We spent three hours talking about what "family obligation" meant in our own respective cultures and upbringings. Nobody taught us to have that conversation, we just stumbled into it because we were curious and had nowhere else to be.

I also remember a very emotional moment with a friend over burgers junior year. I was extremely aloof around my friends, given a huge family event had just occurred in my life that impacted me a lot. We had an honest conversation on how my detachment impacted our friendship. Tears. I apologized badly, then better. We talked through it. I learned that hurting someone's feelings isn't automatically relationship-ending, sometimes it's relationship-deepening if you're both willing to stay in the discomfort.

Maybe your first real relationship happens in college. Emerging adulthood is the crucial period for developing intimate relationship skills and emotional intelligence. You learn what it means to be truly known by another person, for better or worse.

And then there are the spaces we choose to enter as adults. This is where it gets interesting, because unlike childhood or college, you have agency here. Community spaces (book clubs, running groups, hobby meetups, volunteer organizations) become practice grounds for building psychological safety with strangers who share at least one interest with you.

Every Friday evening, I go to this art café in my neighborhood. They have a communal wall where anyone can just show up and paint. No experience required, no pressure to be good, just paint on a wall with strangers. The first time I went, I kept to myself, focused on my section of wall. But something about the shared activity creates this permission structure. Someone commented on my color choice. I asked about their technique. Thirty minutes in, we're talking about why they moved to Brooklyn, what brought them to painting, how they're navigating a career transition they're terrified about.

It's the perfect environment for practicing deep conversation because there's a built-in excuse to be there (painting) that takes the pressure off the interaction itself. You can ease in. You can retreat if needed. The activity gives you something to do with your hands, which somehow makes vulnerability easier. And because everyone's there voluntarily, there's this implicit agreement that we're open to connection.

Honestly, I've had more meaningful conversations at that art café in three months than I've had at networking events in three years. The difference between the two? Nobody's performing. Nobody's optimizing. We're just people painting a wall and sometimes, in between brush strokes, actually talking about things that matter.

There is no playbook (but here's what seems to work)

I can't give you a step-by-step guide to deep conversation. If I could, it wouldn't be genuine. This isn't How to Win Friends and Influence People, and honestly, I'm not trying to influence you into anything. But I can tell you what seems to work, what I'm actively practicing and seeing others practice:

Recognize there's a problem. Not in an alarmist way, but just acknowledge that our default conversational patterns aren't serving us. Notice when you're stuck in pleasantries. Notice when you're hiding behind your phone. Notice when you're performing an emotion rather than feeling it.

Be vulnerable first. Research consistently shows that vulnerability is reciprocal, when one person takes an interpersonal risk by sharing something genuine, others tend to match that level of openness. Not trauma-dumping, but honest acknowledgment. "I'm actually struggling with this" or "I don't have this figured out" opens doors that "Everything's great" keeps closed.

Acknowledge that pleasantries won't get you anywhere meaningful. Use them, then move past them. Ask better questions. "What's been on your mind lately?" works better than "How's work?" "What are you excited about?" goes deeper than "What are your hobbies?"

Be proactively meta about it. If you're with someone and you notice you're having a surface-level conversation, name it. "Hey, can I ask you something more real?" "I feel like we're doing the polite dance, want to skip that?" Most people are relieved when someone gives permission to go deeper.

Practice. Like any skill, deep conversation improves with repetition. Host dinners without phones. Join communities where vulnerability is normalized (therapy, support groups, certain kinds of classes). Go to events alone sometimes, because it forces conversation with strangers. My mentor told me that even if you leave an event having met one person, that is still huge moves than not going.

I don't know if we'll collectively solve this. I don't know if third spaces will return, if social media will get less toxic, if the next generation will grow up better equipped for connection than we are.

But I'm tired of surface-level everything. I'm tired of people checking their phones mid-conversation. I'm tired of treating human connection like an efficiency problem to be optimized. You probably are too.

So I'm trying something different. I'm starting another book club on top of the one I’ve been hosting for two years. I'm taking longer coffee meetings, following up with cool people after events, even when they're "inefficient." I'm asking a ton of follow-up questions. I'm being honest when I don't have it figured out. It won't fix the macro problems. But maybe if enough of us do this, if enough of us insist on depth instead of defaulting to shallowness, we create little pockets of resistance against the loneliness epidemic.

If you made it this far, I'd genuinely love to hear from you. What's your experience been with deep conversation? Where have you found it? Where have you struggled to find it? Email me. Let's actually talk.