July 2026

Investing in Connecting: Friendship in the City

I love cities. But city living isn't for everyone.

The way we exist together in a city—and the way we move through the world—is different. You orient differently. You see differently. You relate differently.

I knew this intellectually. But moving to and living in another city made me understand it in a much more visceral way.

Cities put us in proximity to people we might never otherwise encounter. They compress difference into everyday life. On the subway, in a coffee shop, at a dance class, in an elevator, at work, at a neighborhood bar, you are constantly moving through a world populated by people whose lives may look nothing like yours.

That can be exhilarating.

It can also be lonely.

One of the books I've been reading about friendship, We Should Get Together, takes the practical challenges of making and maintaining friendships seriously—and city life creates a particular set of them.

Finding your people

Cities are full of people. So how do you find yours?

How do you connect when everything is moving, everyone is busy, and you're not sure whether your paths will ever cross again?

There can be a strange feeling in a city that everyone else is somewhere you aren't. Everyone seems to have plans. Everyone seems to know someone. Everyone seems to be going somewhere.

And the sheer volume of possibility can become its own kind of overwhelm.

But I think cities offer something extraordinary that we sometimes overlook: the possibility of encountering people who are different from us.

That's one of my favorite things about friendship.

Friends open your eyes to other ways of living. They introduce you to music you wouldn't have found, food you wouldn't have tried, places you wouldn't have gone, ideas you wouldn't have considered. They teach you customs, languages, dances, ways of operating, ways of thinking.

They make discovery fun.

And cities are particularly good at discovery.

You can encounter someone from another part of the world, another generation, another profession, another culture, another social world—and suddenly your understanding of what is possible gets a little bigger.

That's the beauty of friendship anywhere.

But I think cities amplify it.

I like people

I've never found it particularly difficult to make new friends.

“Make new friends but keep the old, one is silver and the other is gold.”

That was nursery school, and boy, did I take it to heart.

I like people.

Especially at arm's length.

I like activities and action. I have a lot of interests, and I cultivate them—the interests and the friendships.

I'm almost always looking for people to do things with.

Ideally, I like you too.

If we can manage the logistics and actually do something we both enjoy, maybe we can become friends.

Or maybe not.

And either is great.

I think we've made friendship unnecessarily complicated by assuming that every new person we meet needs to become a friend.

Sometimes you just enjoy someone's company.

Sometimes you have one great conversation.

Sometimes you discover a shared interest.

Sometimes you see the same person every Tuesday for six months and know almost nothing about their life.

Sometimes something clicks and you become friends.

Sometimes it doesn't.

All of these are forms of connection.

The beauty of passing connections

I love passing connections.

They lift me.

A smile from a stranger. A funny exchange with someone in line. A conversation with the person sitting next to you. Someone holding the door. A moment of recognition between two people who will probably never see one another again.

Micromoments.

Micro-kindnesses.

One-of-a-kindnesses.

Random acts of loveliness.

There is research behind this, too. Nicholas Epley's work on social connection, including the experiments discussed in A Little More Social, suggests that even small interactions with strangers can make people feel better than we often expect.

We tend to underestimate the value of these encounters.

But perhaps these moments are more important than we realize.

They are the social fabric in motion.

A city is not simply buildings and transportation systems and businesses and institutions. It is also millions of tiny interactions happening between people who may never know one another's names.

It moves.

It breathes.

It works because we are in it together.

And perhaps these small moments of openness are the seeds of friendship: the willingness to engage with someone different from ourselves, balanced with the possibility of recognizing something familiar.

The same and the different.

That's where so much of the good stuff happens.

Do we need instructions?

Maybe it's me, but I can make friends almost anywhere.

Even with my discerning taste.

I'll go to a networking event and somehow come out with friends.

Transactional small talk has never been my strength. Without really intending to, I tend to get to the good stuff.

But I know this isn't true for everyone.

That's especially clear to me from teaching undergraduates.

Some students seem genuinely to struggle to connect with one another. There is awkwardness, certainly. But I think there's something larger going on, too.

The opportunities for connection can be surprisingly limited.

We may be surrounded by people and still lack the structures that help us actually meet them.

Which makes me wonder about books like We Should Get Together.

Do we really need a how-to guide for friendship?

Apparently we do.

And I'm not entirely opposed to the idea.

Dating apps are increasingly moving offline, toward hobby groups and activity-based meetups. I am here for it.

Conversation starters? Sure.

Activities and exercises? Why not.

Training wheels aren't a bad thing if they get you moving.

Maybe we have simply lost some of the infrastructure for making friends and need to rebuild it.

Connection takes participation

This may be what I'm really taking away from thinking about friendship in cities.

Connection doesn't happen simply because other people are nearby.

Proximity creates possibility. Participation creates connection.

You have to go somewhere.

Join something.

Talk to someone.

Ask another question.

Show up again.

Invite someone along.

Make the effort to cross paths twice.

And sometimes, you have to accept that nothing will come of it.

That's okay, too.

Not every interaction needs to become a relationship. Not every relationship needs to become a friendship. Not every friendship needs to last forever.

But a life rich in relationships probably requires a willingness to keep putting yourself into the stream of human interaction.

I think that's what I love about cities.

The possibility is everywhere.

People are everywhere.

Difference is everywhere.

And so are the little opportunities to connect.

The question is whether we notice them—and whether we're willing to invest.

Because connection isn't just something we receive from other people.

It is something we participate in creating.