Leveling Up the Skill of Friendship: Deepening Friendship

A little less than a year ago, in the midst of the very depressing covid lockdown fall, I decided I would write about friendship.

It was a good topic. I had been lamenting about the state of my social life for a while, and writing on the topic seemed like it would be a good idea to improve that part of my life. You could see friendship not just as something that happens, but as a skill that can be practiced and improved. And so I wrote an essay arguing for the importance of developing the friendship skill.

The people who read it liked my essay, but they wanted to know how you could develop that skill. Well — why not write about that too? My single essay grew into a series of three or five essays, depending on how you count. It was going to be the Comprehensive Guide About How To Become Better at Friendship. It was going to cover everything: making friends, keeping them, getting close friends, and dealing with friendship problems.

Here’s some advice: Don’t do this.

Specifically, don’t commit on writing a Comprehensive Guide of any sort, unless you really know what you’re doing.

Writing the first part of my guide took two whole months. I published it on 30 December 2020 because I really wanted it to be done before the end of the year. Then it took me a while to write the second part, which I published in April 2021. In fact it was only half of the second part, because by then I realized it was too long and I had to split it. (Actually, the entire project was originally supposed to be contained in one post. Ah, the naïveté of thinking I could cover everything in a single blog post! I’m pretty sure that one post would have had the length of a book.)

Part 3 never happened until now. There was a draft, lingering from before I split Part 2. There’s some valuable stuff in there, so I’m publishing it today, although, to be honest, this introduction is probably the more interesting section of this post.

What happened? Mostly, I lost interest. Friendship did not turn out to be a topic I wanted to spend months thinking about. Also, I took too long to write it. The excitement waned. There were better topics to focus on.

Here’s some more advice: Write on what you’re interested right now, and don’t count on being still interested weeks, months or years from now.

We do have long (sometimes lifelong) obsessions. You probably already know what most of yours are. Write about those all you want, now, later, whenever. But don’t commit to writing multiple blog posts about a topic that you got into only a few days ago.

With this, here are the contents of Leveling Up the Skill of Friendship: Part 3. It is not comprehensive. Read at your own risk.

Part 4, which was going to be about the problems and the end of friendship, will not be written.

Deepening a friendship

The mark of perfect Friendship is not that help will be given when the pinch comes (of course it will) but that, having been given, it makes no difference at all.

C.S. Lewis

All right, you’ve got a bunch of friends. People you like and who like you. People who are kind and interesting, who are fun to hang out with. People you can rely on for help… to an extent.

But as we saw earlier, there’s a higher level after strangers, acquaintances, and friends. The elite caste: close friends.

Close friends are friends you can rely on for help to a (sometimes surprisingly) large extent. They’re the one you can tell your secrets to. They’re this nourishing presence that will make you feel lucky to be alive. They’re the friends of virtue Aristotle was talking about. The friends for whom the C.S. Lewis quote above is true.

Close friends are much rarer than casual friends, and require much more effort. But they’re incredibly important. And yet not everyone has them; some have only a few. Let’s figure out how to remedy this.

Is there an optimal number of close friends?

Is there an equivalent of Dunbar’s number for close friendships? Yes. In fact, Dunbar’s number should be seen as the size of only one of several concentric circles of relationships. 150 is the value for casual friends. According to Dunbar’s research, the other values are:

  • 50 for close friends that you would invite to a group dinner, for instance
  • 15 for friends you can turn to for help
  • 5 for your core support group (best friends, romantic partners, and family members)

We can immediately see that there are competing definitions of “close friend” here. So the precise number will depend on what exactly you mean.

For instance, the number could be 1. The French philosopher and essayist Michel de Montaigne, describing his relationship with his BFF Étienne de la Boétie, wrote in 1580 that

the perfect friendship I speak of is indivisible; each one gives himself so entirely to his friend, that he has nothing left to distribute to others.

I think we can agree that Montaigne describes a very special kind of friendship, one that approaches the strength and significance of a (fulfilling) romantic relationship. Perhaps indeed you can’t expect to have more than one such friendship in your life.

Most people define close friends differently, though. For instance, in a 2004 poll, Americans said they had, on average, 8 to 9 close friends. 2% had none; 27% had more than 10.

The takeaway from this section is that (again) the numerical value doesn’t matter much. What matter is that you’re satisfied with what you have. If you have fewer close friends that you think is ideal, go ahead and make some.

No threshold, no ceiling

Regardless of how exactly you define a “close friend,” there is no clear-cut point at which a casual friend reaches that level. Friendship exists on a spectrum. This is why I titled the section “Deepening a friendship” rather than “Making close friends.”

There also isn’t a maximum. You can always get to know a friend better and get closer to them. In practice, to get really close to someone, you’ll have to share a significant part of your life with them. That happens mostly in romantic relationships, as well as in familial ones, for instance when growing up with siblings. Or in rare intense bromance situations like with Montaigne and de la Boétie.

So there’s no threshold or ceiling, but is there an optimal level of friendship for any given pair of people? I think so. It seems plausible that two people may do great as casual friends but not make excellent close friends. Or that a pair will be only lukewarm acquaintances until some event brings them close together, at which point they realize how important they are for each other.

I’m not sure, however, that there’s any way to know this optimal level until you reach it — and try to go beyond.

How to create close friendship

To make a close friend, you’ll need time, proximity, repeated interactions, and so on. They’re the basic ingredients — but you’ll need a lot of them. Since the list includes time, you’ll most likely require a lot of patience. The formation of a close friendship generally can’t be rushed.

My friend Daniel Golliher writes that this is accompanied by a feeling of frustration. When you meet someone who’s a lot like you, you wish you could speed through the phase of getting to know each other. It’s like watching a friend discover a book or TV series you love: you can’t wait until they’re done with it so you can discuss it. Daniel continues:

This might otherwise be called the frustration with acquiring old friends. You can’t just make an old friend who’s known you for a while, and consequently understands you more than others might (and vice versa). If you want more friends like this, you have to start today and let them mature over the course of years.

I think this is generally true, but there are some steps we can take to at least make sure we don’t stall the process.

First, as a prerequisite for the rest, let’s mention spending some 1-on-1 time with your friend. That may sound obvious, but you’ll never get very close to anyone if you only ever see them in company of other people.

Be kind, and be kind at a higher level than before. This means providing help at critical moments, especially if their other friends aren’t doing that. Offer your help, and be there when the need arises. Be trustworthy. Don’t be judgmental, except when you need to.

Be interesting. At this level, be interesting in a way that you aren’t with others. Share your weirdness. Share your dreams and ambitions. Become intimate with your friend; show your vulnerability. Trust them, and let strong bonds forge themselves out of your shared secrets.

Create memories between the two of you. Having a history of common experiences allows you to build a solid foundation on which to add the new. It also gives you more conversation options! Sometimes, you might even have not much in common with an old friend, because your interests diverged over time — but the common foundation is sufficient to keep the friendship going and fulfilling.

Catalyzing the process

Is it truly impossible to speed up the deepening of a friendship?

Well, not quite. There are some ways; they boil down to compressing the required time into a shorter period.

The best example might be traveling. Spend a week or two planning day trips, sitting next to each other in a train, maybe even sharing a bedroom with a friend, and you’ll get close, very fast. In such a setting, you have no choice but to become intimate. Plus you create tons of shared memories.

Co-living is another way to set up a life of spending time together. Yet another is to start a collective project — a music band, a startup, whatever.

You may have noticed something in common with all these examples. In each of them, there’s a risk that it will make your relationship worse. Maybe you’ll find that your friend is not reliable when you ask them to plan your travel itinerary. Maybe you’ll find them unbelievably annoying to spend pre-coffee mornings with. Maybe your startup or band will fail and you’ll be certain it’s their fault, and fall out, and that’ll be the end of it.

I think that the idea of risk is inherent to a close friendship. You build trust by showing vulnerability — and that can backfire!

Just like it’s possible to lose a friend by attempting to become a lover, it’s possible to lose a friend by trying to become too close. When that happens, it’s probably best to think that the intimate friendship was never meant to be anyway.

But they1no idea who, this was in my draft with no source lol say that if you’re friends with someone for 7 years, you will probably remain lifelong friends. So if you can’t catalyze the process, don’t worry. Things will get clearer with time.


Feelings of Infinity

I grew up in a small suburb of a mid-size city. The suburb was my world — regular, recognizable, bounded. The city was a vastly richer world. Going downtown meant leaving what I knew to experience something infinitely bigger.

It is a great feeling, the feeling of infinity. It is the feeling that anything is possible. That you can lose yourself in something greater than you are. It is, I think, a precious feeling.

Eventually I went to school in a more urban part of Quebec City. I gained more autonomy, and explored more of the city, and met more of its people. The feeling of infinity subsided. Now it was just a place, and one that I knew fairly well.

I moved to Montreal. Montreal is the core of Quebec’s culture, its nucleus, the city where all the important and interesting people live, the place that you see on TV. It is three to five times more populous than Quebec City, depending on how you count. When I began university, Montreal felt big. It was bustling, overwhelming, brimming with people (and more diverse people, linguistically and ethnically and politically and economically and so on). It was incredibly alive. It was the Place Where Things Happen.

Montreal was the place you saw on TV — but TV gives you just a glimpse of anything, and lets your imagination fill the rest. And yet imagination is limited, so when you move there, it feels gigantic, truly infinite.

I’ve lived in Montreal for about ten years. Today it doesn’t feel infinite at all. It doesn’t quite feel small, and it objectively isn’t. It just feels finite.

Quebec City feels even more finite. Quebec as a whole feels finite now — because Montreal is by far its biggest place, and so there’s nothing else to “conquer,” so to speak. To get the feeling again, I would need to move someplace else. I could move to Toronto, the biggest place in Canada. I could move to the US — a big country, with big cities, surely able to sustain the feeling for a while. Perhaps I should try living in the giant metropolises of Asia.

Maybe focussing on cities isn’t the answer. I love cities, because they offer a far richer experience than other places, but there is plenty of nature to lose oneself into, too. Yet that doesn’t ring very true to me. In part because I’m not a very outdoorsy person, but mostly, I think, because the closest we can get to infinity is through interaction with other humans. After a while, the natural world gets a little boring, a little predictable, in a way that grand landscapes can’t compensate for. I suppose that’s why I eventually quit biology.

When I traveled to a sparsely populated region of Quebec, earlier this month, I was struck by the finiteness of it all. The villages there often have about 200 inhabitants. With such small populations, everyone is the cousin or the sibling of everyone else — there is no illusion of an infinite number of people. The territory was big, and felt more infinite, but not very much more. After all, we have good maps of everything, so there is very little room for the unknown. And the landscapes, while grand and beautiful, are rarely surprising.

In any case, both living and traveling somewhere “consume” your feelings of infinity. After you have known a place, it’s impossible for that place to generate the feeling again. No longer does Europe, where I lived for a year and a half, feel overwhelming. Gorgeous, interesting, yes, but not infinitely so.

And outer space won’t save us. The universe certainly is infinite in space and time, at least relative to the scales of a human life, but it is also mostly empty. What isn’t empty is mostly homogeneous: star plasma and smaller rock. After reading about astronomy for a bit, there isn’t that much new stuff to see. The vastness of the universe can grant you feelings of infinity, but only for a time, like everything else.

In a finite world, the supply of infinity is necessarily finite.

Geography is the easiest way to illustrate what I’m talking about, but it generalizes far beyond that.

There is a meta layer to every human experience. Traveling to Paris and traveling to Tokyo may feel like two very different activities, but they’re both traveling. Recall the first time you traveled somewhere far and different (of, if you never did that, imagine the first time that you will). The excitement of being in a plane, right before takeoff, for your first flight; the exoticness of seeing everything written in a language you don’t understand. Those things can only be lived once. So even though I have traveled only in a limited part of the world,1a quadrilateral whose extremes are Vancouver in the west, northern Sweden in the north, Israel in the east and Nicaragua in the south I don’t get a strong feeling of infinity anymore when I travel (I still love travelling, however).

And so it goes with every human activity — watching a movie, going to a party, having sex with someone, making a new friend, learning a language, practicing a sport, writing a blog post. You can do these things infinitely many times, and there will always be variations, but they will not provide you with an overwhelmingly new experience each time. For every new type of activity you experience, your world gets a little more finite.

The question becomes: are there enough sufficiently distinct types of activities to sustain a person’s feelings of infinity for their entire life?

It’s possible that there is. Unless something major happens, I expect to be alive for 50 to 60 more years. There are still plenty of experiences I’ve never tried, like raising a child, going to space, trying almost any drug, or leading a company, and it’s conceivable that these things have the potential to fill the rest of my life.

But sometimes, especially when I’m feeling down, I worry that they won’t. That eventually, perhaps soon, I’ll have exhausted my supply, and will almost never feel infinity anymore. It scares me.

I don’t want this post to be depressing, though. Let’s explore some possible ways out of this.

One first path is to manage the resource. If a person’s lifetime feelings of infinity come in a limited supply, it implies that we can decide when and how to consume it, like we can manage a limited supply of money.

This suggests that we should be smart about seeking new experiences. We shouldn’t try to sample all the foods and visit all the countries too fast — lest we become jaded and feel the world shrink. We should carefully manage how much we are exposed to the vastness of the world, so that it remains vast for a long time.

This sounds… fine, I guess. Smart management is good, but it’s also kind of lame. Carefully managing a small amount of money is better than spending it all and cornering yourself into a bad situation — but if you can, it’s far better to make more money.

But perhaps the analogy with money isn’t good, because while money is necessary for good living, feelings of infinity are only a luxury. You can simply accept that at some point you will run out. So another path to dealing with the finiteness of the world is to embrace it. Find beauty and meaning in smallness. Enjoy the minute variations between different instances of an experience — movies, travels, sex, whatever you want — instead of seeking completely novel types of experiences.

I think in general it’s smart to be able to find happiness from a variety of sources, including the mundane. But feelings of awe, of infinity, can be transformative experiences; it would be sad if we got less and less of them as we grow; it would be a great loss.

Maybe there is a way to engineer infinity, to add it to our lives when we lack it. Psychedelic drugs, which I’ve never tried, sound like they may be able to do that. Meditation, too. In fact that may be the main purpose of religion: to construct stories about something so much greater than we are — the divine — in which we can get lost.

Another possible way to engineer infinity is through art. Each new piece of literature, of film, of painting, can be a little fragment of infinity that we get to experience. And there is more art being created than we can consume; it is like the expanding universe, growing faster than we could ever travel even if we reached the speed of light.

Art forms are finite and can feel so after a time. But one great thing about art is that it attempts, by its very nature, to surprise and expand our experiences. The most successful artists make us see in ways we couldn’t before. New forms of art get invented, providing the new types of experiences I was talking about. So art is in some sense infinite — at least as long as artists make sufficient amounts of it.

And this brings us to the only true way to avoid shortages of infinity: expanding human civilization. Make more art. Invent more things. Make more humans, too.

Children seem like a good way to vicariously get feelings of infinity (among other things). Everything is big and impressive for a child; watching them experience the world can give us a glimpse of what we once felt. But the impact of having children is far greater than this.

Having children means continuing and augmenting human civilization. It means more people who will make art and create new ways to experience life. It means more people who will create new subcultures and colonize planets and make more children in their turn to keep the cycle going, until one day we have reached all the stars that we can.

I didn’t expect this essay to become a defence of pronatalism, but here we are. More people is a good thing for many reasons; creating infinity may not be the main argument, but it’s a poetic one, which is maybe more convincing than any of the others ones.

It is night, at the end of summer.

I am at my computer finishing an essay, or perhaps, rather, a meditation, about infinity.

I sit in a fairly small room, with only one window. It doesn’t get enough sunlight, but that doesn’t matter right now.

Outside is a city. Several million people, living complex and beautiful lives. I will never meet all of them.

The city is on a big rock. That rock is the Earth. It is finite, but it is also vast. I will never see all of it.

The Earth is set in a mind-bogglingly large universe. I will never even know what happens in most of it.

Inside my computer is a portal to a vast hypertext library of human knowledge and art. I will never read or see all of it.

I am feeling infinity again. It is a good feeling; I hope I can sustain it for a while.


Leveling Up the Skill of Friendship: Maintenance

Wishing to be friends is quick work, but friendship is a slow ripening fruit. — Aristotle


How many friends have you lost contact with for… no specific reason at all?

It seems to happen all the time, doesn’t it? We like to tell new friends, “let’s keep in touch,” but then we don’t. Our past is littered with abandoned friendships.

In a sense, this is expected. Friendships have a life cycle and most don’t last forever. If you’re continually making new, better friends, you should expect to have less time for your existing friendships. Those then wither and die. Or, more often, they enter permanent stasis, frozen in time until something stirs them up again.

But sometimes, friendships wither and die and enter permanent stasis simply because we haven’t put in the maintenance work.

“Maintenance.” Not a very sexy word. It brings to mind a whole part of the lexicon we’d prefer never to think about: “chores,” “cleaning,” “troubleshooting,” “calling a plumber because the kitchen sink is a disgusting mess,” and so on. Yet everyone recognizes that maintenance is necessary. It’s unsexy work, but it’s work that must be done — otherwise the kitchen sink becomes grimy and might break down and then you’ll definitely need to call an expensive plumber.

This analogy is imperfect because maintaining a friendship is much brighter and more fun than taking care of yucky plumbing. But it’s worth emphasizing that it’s not as effortless as we might like. You need to take care of your friendships, to nurture them, or they will most likely break down or become forgotten.

Here are my thoughts on how to do this. I don’t claim to be an authority — I’m just someone who’s figuring it out, and who does that through writing an essay like this one. I think and hope it will be useful to you, too.

Table of Contents

This is part 2.2 of my series on friendship. You can access the previous parts, on why friendship matters and how to make new friends, from this table of contents. You can also jump to any of the subsections:

Pierre-Auguste Renoir - Luncheon of the Boating Party - Google Art Project.jpg

More classic art (Luncheon of the Boating Party by Renoir) to represent friendship, in this case showcasing how wine, food, and cool hats are the key to keeping good lifelong friends

Recognizing that friendship is not effortless

When I was writing this, I had an open email window on my laptop. The window was mostly empty. There was a friend’s email address in the To field. Then there was the very beginning of an email, something like “Hey, how’s it going?” Nothing more.

This is a friend with whom, years ago, I used to communicate via long, old-fashioned emails. I hadn’t talked with him since 2018, and I’d been meaning to reestablish contact with the same mode of communication as before.

That email stayed both open and unwritten on my computer for about three months, until — coincidentally enough — that friend contacted me through some other means, making me slightly ashamed to have waited until then.

Why didn’t I write that email? Not because I didn’t know what to say. Not because I was afraid of his reaction, or because I didn’t care about that friend.

Simply because it was work.

Communication is not effortless. It’s not always a huge effort — sending a text message to a close friend is pretty easy — but it’s more effort than doing nothing. And communication is only part of a relationship. People need love, help, support, and time. You need to be ready to give those out to the people who are important to you. None of that is effortless.

From an essay called “Friendship is work, and that’s okay“:

Just like romantic partnerships and family relationships, friendships require a delicate balance of compromising, apologizing, spending quality time, and even calling out inconsiderate or upsetting behavior instead of bottling it up.

We often don’t realize that friendship demands effort, because it is usually very enjoyable. Which is great! That’s why we want friends to begin with. But the need for work can be obscured by that enjoyment, and then we don’t realize we haven’t done enough, and then our friendship suffers.

So the first part of my maintenance advice can be summarized thus: recognize that friendship is work.

Avoid the somehow widespread view that friendship happens magically.1yeah, I realize I’m the one who put a My Little Pony: Friendship is Magic image in the last post. It is magic, but only in the sense of spending hours drawing pentagrams and incanting complicated spells. Magic is work! That they’re governed by fate. It’s seductive to think lifelong friendships are created instantly through the mere act of meeting a kindred spirit. Just like it’s seductive to think that romantic love is all about finding your soulmate and spending the rest of your life in unending bliss…

… which everyone who has been in an actual romantic relationship knows is bullshit. Romantic love is hard. But somehow we haven’t internalized the same lesson about friendship.

Keeping a friend you’ve just made

Maintenance work starts as soon as friendship is born. But at first, it’s usually easy work.

This is because the conditions that provided the initial spark are still there. That friend you made at work will remain your friend as long as both of you keep your job. Friends you met when you became passionate about your theater classes will easily stay friends with you as long as you’re into theater.

Let’s point out that almost everything in the make new friends section from the last essay still applies. If you keep doing whatever made your acquaintance turn into a friend in the first place — being kind, being interesting, making the relationship easy for them — then the friendship is likely to endure.

At least, until the conditions change. If you can control it, and care a lot about the friendships you made in some context, try whatever you can to keep the conditions constant. But of course, there are a lot of life circumstances we can’t control, such as finishing school or quitting a job, losing interest in theater classes, or simply having friends leave for their own reasons. And even when we are in control, other considerations — a career, a romantic relationship, family, etc. — will force us to sacrifice the ideal environment to keep our friendships. What then?

Keeping in touch when conditions change

That’s where the real challenge of friendship maintenance occurs.

How do you keep your friends from high school or university or your first summer job or the hometown you’ve left years ago?

How do you keep friends that you met through someone who’s no longer in your life — for instance, the friends of an ex?

One answer is that sometimes, your friendship was tied to that bygone context to such an extent that it will never be the same again, and you shouldn’t try. But that certainly isn’t always true.

If you’re intent on staying friends even after circumstances are bringing you apart, you’ll need to put in some more maintenance work. The first step is to initiate contact frequently. People are bad at reaching out. People vaguely think about contacting you, and then they keep a draft message open for three months and never send it. You can’t fix that for them, but you can fix it for yourself and maintain your friendships that way.

One trap you want to avoid is to assume that if a friend hasn’t contacted you already, it means that they don’t want to see you. It’s really easy to think that, especially if you’re shy or socially anxious!2Source: am a shy and socially anxious person, or at least I used to be. But it’s also easy to convince yourself that it’s almost never true — just realize that your friend might be making the exact same assumption, since you also haven’t contacted them for exactly as long.

Of course, it’s sometimes the case that someone you consider a friend doesn’t want to see you anymore. You need to read the room. If you’re always the one initiating contact and your friend doesn’t seem that keen to see you, you might want to stop trying. We’ll consider this in more detail in the essay on ending friendship. But I want to say this: a long time with no contact is not by itself evidence of unrequited friendship.

Concretely, what does maintaining a friendship look like?

It can be as simple as a “maintenance text” — just sending a short message every once in a while. My friend Rishi writes, in How I keep in touch with friends after college:

It can be a:

  • Dank meme
  • Interesting article
  • Piece of sports news
  • Shared memory
  • etc.

Receiving any of those things means the other person was thinking of you, which is just the sweetest thing.

It can go further, of course. Invite your friend over. Grab some food or play a game. Suggest a phone call or video chat. If they live far away and you can afford it,3and there’s none of this horrible covid-19 thing restricting travel travel to visit them! As a bonus, they’ll even be able to show you around, which is the best way to do tourism.

Some occasions are particularly suitable for maintenance texts/calls/etc. Birthdays, for instance: you have the perfect excuse to send something to a friend — so why not add to your birthday wishes something like “We should have a call, it’s been a while!” Your own birthday is also a good time to suggest hanging out to whoever is sending you wishes. Other holidays, e.g. New Year’s Day, are similarly convenient.

Those calendar events are Schelling points — easy dates to coordinate around by default. But you can also create your own recurring events with a friend. For example, decide that you both go watch a movie at the beginning of each month. In other words, create a habit — which is one of the best ways to make work not feel like work.


Not everyone is that bad at reaching out, and so you will also be on the receiving end for many of your friendships. My suggestion, if you care about those friends, is to make a habit of replying quickly when they contact you. In fact, make a habit of saying yes to whatever they’re inviting you to — or, if you must say no, immediately reschedule or suggest another activity.

There’s a real danger, when you decline invitations too often, of letting your friends think you don’t want to see them. It helps to directly tell them that it’s not the case. Say “Sorry, I’m really too busy this week, but I’m really happy you invited me! How about we grab lunch together next week?”

(I have a friend who told me something like that, and it truly warmed my heart. But it’s been a couple of months now. Hopefully that wasn’t a strategy to tactfully get rid of me.)

If on the other hand you don’t care about those friends, well, perhaps friends isn’t quite the right word then. This is a matter for when I’ll write about the end of friendship.

You may also find yourself on the side of doing the work alone, with no reciprocity. This is not an ideal situation. As I mentioned earlier, that may just mean the friend isn’t very skilled at friendship, but it could mean they’re the ones who don’t care that much about your relationship. As a friend told me, “even a ‘well-maintained’ friendship can crumble if the maintenance work isn’t shared.” I don’t think the work should necessarily be shared equally, but it can’t all fall on the shoulders of a single person. That’s too much to bear.


If you have a lot of friends and acquaintances, that’s… a lot of data to keep track of, actually. There’s basic stuff like birthdays and email addresses, but also who likes what kind of food, who has feelings for whom, who enjoys what sort of event… Humans do come equipped with a lot of mental power to process social data — for around 150 friends, to bring up Dunbar’s number again — but there’s no shame in getting a bit of technological help.

For many, social media data is largely sufficient. Facebook will remind you of birthdays and provide a convenient way to contact people. But not everyone is on whatever social media you’re using (probably for good reason), so you might still want to take extra notes. It can be as simple as keeping track of email and physical addresses in a notebook or text file.

But you can get fancier. Nat Eliason has a detailed blog post on what he calls his personal CRM (contact relationship management) system. He keeps track of:

  • First & last name, email
  • Industry / skills, Company
  • Interests
  • Location
  • How we met

I don’t think that this particular solution fits everyone, but I’ve started doing something low-key similar, and so far I like it. Sometimes there are little details about people that you’re not going to remember by yourself. For instance, I have a friend whose taste buds will not tolerate cilantro. If I invite her over for dinner, and look at my few notes about her, I will not cook food with lots of cilantro (I love cilantro). Everyone wins!

Is it weird, though, to take detailed notes on people? It somehow feels like it goes against some social norms — yet I can’t really see why. You keep information and impressions of people in your head all the time; it’s not very different to keep them in written form, as long as they remain private. Still, I rarely write anything personal in my own notes, perhaps because it’d feel like a transgression. I suppose the answer here depends on your own level of comfort.

Scaling it up

Everything I’ve told you so far is useful,4at least I hope so but it all assumes we’re talking about 1-on-1 relationships. If you have a fair number of friendships you want to maintain, it’ll be a lot of work, both for you and each of your friends. Fortunately, there are ways to become more efficient.5“Efficient” might sound too productivity-centered for something as sacred and beautiful as human relationships, but even if you don’t think of it in those terms, you still need to be efficient! You have limited energy to do the work of maintenance and it’s good to be wise about how you spend it.

Am I just going to tell you to see several friends at once? Yeah. Organizing a group event requires more work than a 1-on-1 — scheduling is more complicated, and maybe you need to get your house in order if you’re hosting — but it’s often worth it. It’s rewarding, it makes people happy to be invited, and you see many of them at once in a fun context.

But if you’re going to organize a hangout with many friends, why not make it recurring? I already mentioned that creating habits is a good way to foster a 1-on-1 friendship; that’s even more true for group events. Make them low-key, with flexible guest lists, so that they happen regardless of any specific friend’s availability — and suddenly you have created a Schelling point for a whole group of people.

Weekly dinners are perhaps the most common example. I lived in the Boston area for a little while, and the Friday evenings at some friends’ group house were a highlight of my time there. There was something really warm with the idea of joining this ever-changing group of people6there was, however, a core of regulars, which I suspect is a prerequisite for the event to persist over time for fun discussions and food every week.

It doesn’t have to be weekly, though — monthly or even yearly recurring events can work great. It can also go beyond dinner parties, like outdoor activities or game nights, as long as the events don’t get too complicated or costly.

The whole idea is to make it easy for your friends to join. To perform the maintenance work for them. This reduces the total amount of work needed, and isn’t much harder than organizing 1-on-1 hangouts.

Self-sustaining friendship

There is a final trick I need to tell you about, and it is the best trick of all. With this strategy, you can make the work of friendship maintenance perform itself with minimal effort, most of the time. The trick is to create a virtuous cycle, in which friendship begets friendship.

Friend groups are the logical next step to recurring group events. When you have a cohesive set of people who see each other regularly, eventually the group seems to get an identity of its own. It becomes a tribe; you get a feeling of belonging. But more importantly, the group’s continued existence depends on very little individual maintenance work; everyone can contribute, to the advantage of everyone else.

Rishi writes:

If you’re like me, you can’t be trusted to maintain a friendship 1:1 by calling and texting all the time. You get busy. In a friend group situation, your amazing friends keep each other engaged. This way, you’re relying on a system instead of willpower.

You still need to contribute some; if no one does the maintenance work, the group will disintegrate. In fact it’s likely that the distribution of work is unequal — we all know of situations where one friend is responsible for holding the group together. Which isn’t necessarily problematic, except insofar as it makes the group fragile.

But in an ideal group, any effort you put in will be amplified by your other friends, and their actions will be in turn amplified by you. Thus the system becomes self-sustaining.

Concretely, the easiest way to get this is to join an existing friend group, though you can also create your own. The means are diverse: recurring events, co-living, common projects, or simply online chat groups.

There is another, more personal type of self-sustaining friendship: deep friendship.

When you get very close to someone, it doesn’t really matter whether you send a text message every once in a while. You can in fact spend years without any contact. “No matter how long you spend apart, when you come back with your friend, it is like no time has passed at all,” as C.S. Lewis wrote.

The ordinary maintenance work becomes unnecessary, or so easy to do that it goes unnoticed — although perhaps that is an illusion. We’re less at risk of losing a close friend due to neglect, but when help must be given, for instance in times of crisis, the demands will be greater. Maintenance work is still needed, but its nature has changed.

Still, deep friendship is rewarding and less taxing in our daily lives. It’s a whole other topic, however. We’ll cover it in the next post.


Thanks to Gregory Yang Kam Wing, Taylor Pullinger, and the wonderful people in Writing Workshop Juliet for feedback on this piece.


Leveling Up the Skill of Friendship: How to Make Friends

Do you feel lonely?

Do you think your current relationships are unfulfilling?

Did you just move to a new city and haven’t built a social circle yet? Do you feel like your career or intellectual life is stuck? Are you unhappy with your romantic relationships? Does your life lack purpose?

The solution to all of these problems is simple. Make friends!

And keep them. And get the most out of your relationship with them.

In my previous essay on the topic, I argued that friendship is a skill, and that it’s an important one. Perhaps the most important.

This 3-part essay is about how to level up this skill.

Table of Contents

This was initially meant to be a single essay, but it grew into an untamable beast. I had to cut it into three smaller critters.

I like to divide the skill of friendship into five subskills, which form what we can call the cycle of friendship. The post you’re currently reading is Part 1 (or Part 2.1, I guess, if we count the why essay as the first part) and covers the first subskill, about making friends.

It’s hard to find classic paintings to represent friendship, but I think this one (A Tale From the Decameron, John William Waterhouse) does a decent job


A friend is someone who knows all about you and still loves you.
― Elbert Hubbard

I’m not, by any means, the first to write about friendship. The tradition goes back a long way. At least 2,360 years ago, in fact, ever since Aristotle dedicated two books of his Nicomachean Ethics to friendship. I could cite many more authors, but you can just look up famous quotes on friendship1some of which I stole shamelessly as section epigraphs and you’ll get the idea.

This isn’t surprising. We’re a social species. Developing bonds with others is a big part of what it means to be human, so of course thinkers have always been writing about friendship.

Yet there can be no shortage of writing about it. Because friendship, like love, or family life, or work, is an endlessly complex and central facet of human life. It is always worth refining our conception of it — and coming up with good advice to improve the skill.

I’m not calling this “The Ultimate Guide to Friendship,” because I don’t see myself as anything like an expert, and “ultimate” would sound pretentious. But I do want it to serve as a useful repository, with lots of links and quotations. Some by famous authors or ancient philosophers. Others by popular bloggers and personal friends of mine. This is meant to be nothing more than a compilation of advice, wrapped with discussion to make sense of it all.

It’s also meant to be a living document. I plan on continuously updating the post as I find more of the best advice.

What is a friendship, exactly?

A friendship is a relationship between two people who like each other. The each other part is important. If it’s not mutual, it’s not a friendship.

This implies that to be friends with someone, you have to be likable to them — and they to you. Each of you has to provide something that the other values.

Aristotle identified three types of friendship based on three types of values: the useful, the pleasurable, and the virtuous. It is clear from reading Aristotle that the third type is the “ideal” or “true” friendship. There’s nothing wrong with relationships that are based only on mutual utility or pleasure; but the most fulfilling bonds are those that we make because we value the other person for themselves, rather than for whatever benefits they bring us. That’s what we’ll be focusing on here.

In my view, the two main qualities you need to be a great (or virtuous) friend are kindness and interestingness. Kindness can be seen as giving support and love. Interestingness can be seen as bringing value and fun.

Importantly, you need both.

Imagine a person who’s very kind, always willing to help others. You’re glad to have him in your life when you need something. But you also can’t help but think he’s a bit dull. He never voices opinions. You don’t know what his tastes are. Or his ambitions. His dreams. He works some ordinary job — or so you assume, because he rarely talks about it. He has no known hobbies. You call for his help every once in a while, but you always feel some unease, and as soon as the help is given, you leave, not wanting to feel the awkwardness of hanging out with someone who bores you.

Now imagine another person, one who’s super interesting. She has a crazy life, always a cool story to tell, endless facts to teach. But she’s also kinda mean. She asks for help but rarely gives it. She is great at sarcasm — and you laugh each time she demolishes something or someone with her deadpan humor, but not quite in a wholesome, feel good way. You’re glad you know her, because she’s fun to watch. But you don’t want to get too close. She radiates an aura of mild toxicity.

Would you want to be friends with either of them?

Of course, people contain multitudes. Kindness and interestingness can be shown — or interpreted — in many ways. But the first step to becoming good at friendship is to ask yourself, whenever you interact with people you like: Am I being kind? And am I being interesting?

I think that if you focus on this, instead of worrying too much about social norms, you can go a long way.

With that, let’s dive into the first step of the friendship life cycle: making friends.

Making new friends

Of all the means to insure happiness throughout the whole life, by far the most important is the acquisition of friends.


The first step to being good at friendship is, quite obviously, to have friends.

This section is relevant to you if you feel like you have no friends, or don’t have enough, or you have “friends,” but they’re not real friends. But anyone can benefit from being better at making new friends.

Concentric circles

Here’s a common way of categorizing relationships. We can view each category as a set that includes the ones after, like concentric circles:

  1. Stranger
  2. Acquaintance
  3. Friend
  4. Close friend

When we talk about making friends, we talk about moving people from stranger to acquaintance, and then from acquaintance to friend. (The friend to close friend transition will be covered in part 2.2.)

Is there an optimal number of friends?

The anthropologist Robin Dunbar famously estimated the number of stable relationships a person can cognitively maintain, based on observations of primate brains. The average number is 150 — though the real value falls into a range of 100 to 200 depending on each individual’s circumstances.

For the purposes of Dunbar’s number, a friend is someone “you would not feel embarrassed about joining uninvited for a drink if you happened to bump into them in a bar,” in the words of Dunbar himself.2From his book Grooming, gossip, and the evolution of language, p. 77 We’re free to give the word “friend” a more or less strict definition, and change the number accordingly. But the point remains: there may be a higher limit to the number of friendships we can have.

Does that mean it’s possible to make too many friends?

Past me definitely did believe this. I used to routinely tell myself that I had sufficient friends and didn’t want more. (And yet, I was probably nowhere near 150 friends at the time.) Present me realizes that this was a cop-out. It was a way for Past me to avoid facing the fact that he wasn’t very good at making friends.

Present me doesn’t think that you can make too many friends anymore.

See, Dunbar’s number is not a hard limit; it’s a soft one. You can always meet new people, and if a meaningful connection forms, you befriend them. If you happen to already have maxed out your cognitive capacities for relationships, well, at worst, one of your 150 will be bumped into the lower tier of acquaintances. In fact, it is expected that the exact contents of each group change over time.

The only downside to making a new friend is the opportunity cost. The time and energy could have been spent doing something else, making another friend instead, or hanging out with people who are already your friends.

If you’re 100% satisfied with your social life, and new friends would mean less time with your amazing current friends, then feel free to skip the rest of this post. Otherwise, making new friends is the way to improve your social circle. You should be spending most of your precious time with the people that you prefer — and your preferences can change. Unlike with romantic relationships, there is no expectation that your current friendships stay stable forever. They’re always in flux.

Finding potential friends

As of writing this, there are more than 7.8 billion people in the world. Actually, let’s write this number in full. 7,800,000,000. Go here to visualize how many that is. (Warning: that website is somewhat dizzying!)

screenshot from Dec 20, 2020, showing a tiny fraction of humanity

You personally know a few hundred of those, which means that there’s approximately 7,800,000,000 you could potentially get to know. Yes, that’s the same number, because on this scale, a few hundred is a rounding error.

Now, not many of them are people you would like to have as friends, nor would most of them be interested in you. Also, well, most of them don’t speak your language, some are babies, some are twice as old or young as you are, and some live in North Korea. But the point is that the world is big. No matter who you are, there is the numeric potential to make new friends. You can never run out.

Visakan Veerasamy (a.k.a. Visa3this essay does not talk about credit card companies, so you can safely assume “Visa” refers to him) writes:

there are a *lot* of people in the world, we chronically underestimate this

Meeting strangers

So, how do we meet all these strangers? They’re all around us, obviously, but how do we talk to them?

Here’s a recipe:

  • go within hearing distance of some people;
  • open your mouth;
  • utter some words.

Okay, I know, it’s not so easy in real life. Talking to strangers is scary! Especially if you’re shy or introverted (as am I).

It’s possible to bond with strangers by talking to them in a park, or coffee shop, or grocery store. But it’s not the most common way to do it. Author Kio Stark has some interesting insights about that, but when I read her piece on experimenting with talking to strangers, I couldn’t bring myself to apply any of it. (Well, except for the “observe and take notes” part.)

An easier way is to put yourself in an environment where talking with strangers is normal and expected. That is, go to public events: there’ll be people you don’t know, and who share an interest with you.4yeah, don’t go to an event you’re not interested in, that won’t be fun for anyone That makes it simple to strike up a conversation!

These events can be anything: shows, classes, hobbyist activities, organized sports, etc. They can be online events, too. Bonus points if it’s regular — you’ll keep seeing the same people, which builds familiarity. Bonus points, too, if the activity involves interacting with other attendees. As an example, improv worked well for me. Board game nights — or any sort of event where you play, really — are a great hack: games makes everything easier by providing a clear framework for social interaction.

A good mindset to adopt is to say yes by default. Unless you have a good reason, if you’re invited somewhere, go — even if you don’t feel like going very much. Even if you’re shy.

I love this six-month experiment by Default Friend (yes, her pseudonym is very topical):

When I first moved to California, and long before the days of COVID-19, I would go to any part of the Bay Area, at any time, to do (almost!) anything with anyone. . . .

I’d say I made in the neighborhood of twenty friends using this approach. Five or six close friends. Plenty of acquaintances. Tons of people who linger in the space between “I like you a lot,” and “the timing just hasn’t been right yet.” . . .

Anyway, that’s what “default friend” means. In some ways, it’s living your life like it’s an improv show.

It’s responding to every offer with a, “Yes, and…”

If and once you have an existing network of friends, you can also use it to expand your social life. Go to events with your friends. Ask them for introductions to other people they think you’d get along with. Get to know your friends’ friends. This has the extra benefit of creating friend groups, which are valuable in themselves.

From stranger to acquaintance

Okay, you’ve met a stranger. You said hi. Now what?

On the path to making a new friend, you’ll have to cross the stage of acquaintance. What does it mean to make an acquaintance out of a stranger?

Not much, depending on how you define “knowing” someone. Just saying “hello” isn’t enough, but as soon as you have a real conversation, or know each other’s names, or know how to get in touch again, then that’s it. You’re acquainted.

It helps, here as elsewhere, to be kind and interesting. Kindness with a stranger translates to being polite, warm, open to give help. Interestingness means being able to have a good first conversation, and that goes beyond small talk.

Small talk is useful, of course. It’s a skill of its own. Mastering it will make it easier to talk with strangers, since by definition you don’t know what you share with them — so you often need mundane topics like the weather to get started. But if you can’t dive into deeper topics after a little while of talking with someone, it may be hard to have the meaningful conversations that will build friendship over time.

(But note that the length of that little while can vary enormously depending on the person! Some are allergic to small talk, so avoid it as soon as possible; others can be fun to talk with about ordinary things for hours. There will be signs — read them.)

Acquaintances aren’t what we’re after — we tend to have a lot of them, and they don’t necessarily bring a lot of value to our lives. Besides, they take up some of our time, so they’re not free. But they’re a necessary first step, and having a large network of acquaintances can certainly be useful.

From acquaintance to friend

To make a friend out of a person you know, you need repeated interactions. Phrased differently, you need time and proximity. You need to share experiences and memories.

You may be lucky and develop a bond very quickly with someone, if you have exceptional compatibility5Or if the circumstances give you lots of repeated interactions in a short amount of time, which is just a compression of the above. But in most cases, it’ll take a while until you can call someone a friend. That’s okay. Don’t expect it to be fast. Focus on being kind and interesting — provide help, compliments, fun times — and you’ll get there.

Or you won’t, in which case the best course of action is to befriend someone else instead.

Let’s emphasize this point: you can’t force a friendship, so it’s useful to recognize when an acquaintance won’t bloom into a true friendship. One sign that your friendship won’t work is if you’re consistently the only one reaching out to the other person. Since a friendship has to be mutual by definition, if you find yourself in a one-sided situation, you should quickly move on.

Which brings us to the actionable advice in this section: do reach out! Unless you’re in the workplace or some environment where you meet the same people regularly, repeated interactions won’t happen by magic.

From Alexey Guzey’s How to make friends over the internet:

90% of meeting people is reaching out, so, unless you’re already very well-known, most of your network building will consist of actively initiating conversations.

This applies to online environments, and the 90% figure might be lower in the physical world. But the point stands: you’ll get much faster results if you try to make friendship happen rather than wait for it.

In fact, my personal experience is that the vast majority of people are really bad at reaching out. They just… don’t. Or rarely, anyway, especially with people they don’t know well yet. So if you also don’t reach out, you’ll end up becoming friends only with the small set of people who do, and it’ll take a long time.

What should you tell people when you reach out? Be kind and interesting, sure. But a more precise piece of advice is to make it easy for the person. They’re not your friend yet, so they won’t necessarily want to put a lot of effort into knowing you.

Ask them things — people love to help! — but ask them straightforward, specific things. It’s fine to suggest just to “connect” or “hang out,” but then do the work of finding a place and time, instead of hoping that they do it for you.

Especially avoid asking vague questions like “Will you be my friend?” It’s awkward, it rarely works, and it puts the onus on the other person to figure out what is it exactly that you want. Visa again:

“Can I know you?” “Will you be my friend?” “I think I’ve fallen in love with you” are all selfish, short-sighted, things to say that force the other person to do all the work of figuring out the relationship you’re trying to establish.

Instead of asking, “I’m lonely, please be my friend,” ask “I’m having a rough day, would you like to take a thirty minute walk with me tonight after work?” It’s much easier to say yes to that.


In the very weird but ever growing online world, making friends also requires being kind and interesting. But these words take slightly different meanings.

Let’s start with interestingness. To be interesting online, well, the first step is to put stuff online.

In other words, create. Write a blog, a newsletter, thoughtful comments on other people’s stuff, social media posts, anything. It doesn’t have to be writing, actually. You can make videos or post pictures or whatever you like. But you need to have an online presence. You need to exist.

Ideally, create well. If you manage to build an interesting online presence, you’ll attract people. You’ll craft your “personal bat signal6this is a Batman reference, even though I know next to nothing about Batman that people recognize. But don’t let the need to create “well” stop you; quality is much less important than just showing up, and showing up often.

Use social media actively, not passively.7This is also a good way to make social media have a positive rather than negative impact on your life. Passive use of social media might be linked to depressive symptoms. Yet the vast majority of people don’t really engage actively. Despite what you may think, Twitter is a good place to make friends. I can vouch for that — I’ve started using Twitter seriously a few months ago and I have, as a matter of fact, made friends through it.

At this point, the fraction of my readers who don’t use Twitter will be thinking: wait, isn’t Twitter literally the worst place on the internet?

I don’t know. Maybe it is. But I just don’t hang around the bad parts. I keep to the parts where people are being kind.

For some reason, it seems people easily forget to be kind when they’re online. Trolls roam about, ready to insult anyone who comes close. Disagreements are pretexts for insults. We’re always a few bad comments away from a flame war.

I don’t know why we do that. Human nature, I guess. But it’s easy for you not to do it. Just be kind. Give compliments. Voice your opposition in a mild, pleasant manner. Follow the common improv8You may have noted this is the third improv reference in the essay. I feel that there’s a deep connection between friendship and improvisation. But that would be another essay. advice: say “yes, and…” to validate other people’s comments before adding your input.

And then, reach out. When you’ve interacted with people that seem interesting, send them a direct message or an email. 90% of meeting people is reaching out! From Alexey Guzey again:

any platform that allows you to send private messages to people is a platform where you can make friends.

  • on reddit, when you see a comment or a post in which the author seems like somebody you want to be friends with, message them
  • on Goodreads, when you see a book review that really speaks to you, message the author and share your thoughts on it
  • on someone’s personal site, when you enjoy the writing, shoot them an email and let them know about it

The essay goes on to describe 20 examples of people Alexey Guzey met through direct messaging.9It’s also interesting because he used to to not have any friends. Advice from someone who had a problem and then solved it is the best kind of advice. He also recommended the book The Science of Making Friends: Helping Socially Challenged Teens and Young Adults, which I haven’t read, but seems of great interest for people with autism, ADHD and other such conditions. You can go read it (it’s really good), but I’d rather you finish my essay instead, so here’s one example of how it went for me with Twitter.

There was this guy I had noticed a few times in the endless chaos of the Twitter feed, without really giving it much thought. Eventually I realized he was part of a community I also am in (online communities are a great way to make friends!), but also, especially, that part of his Twitter bio was exactly the same as mine from before I used Twitter seriously. Which suggested we had similar interests and ways of thinking.

Armed with these two pieces of information, I followed him; he followed back, I think (I’m not sure of the exact order of these events); and then sent him a direct message (a.k.a. a DM). I said something to the effect of “Hi! I wanted to say that the reason I followed you was [thing in common #1] but also [thing in common #2].” He replied back, and then we had some small talk in the DMs, for instance about what our personal projects were. That lasted for a few days. Soon enough, we had a Zoom call. Since then, we’ve had another call, and interacted a lot through DMs and as part of the online community I mentioned. Someday, when travel is open once again, I’m sure we’ll meet in real life.

The process will never go exactly like this again. But we can abstract it into the following steps:

  • Find someone who interests you
  • Optional: interact in public (Twitter comments, forum discussions, etc.)
  • Reach out in a private channel (DMs, email, etc.)
  • Converse
  • Meet in real life, video call, etc.

Making new friends online is weird, in a way. It has been happening for a couple decades now, but we still haven’t really built norms around it. Yet, it will happen more and more. And it can happen to you, if you make it.

Aaaand I’m done with Part 2.1. I hope it will be useful to someone. Writing it has certainly been useful to me. (Here’s to hoping this very essay will land me some amazing new friends!)

Next up, in Part 2.2, we’ll cover close friendships and friendship maintenance. Feel free to subscribe to the blog or to the newsletter to make sure you don’t miss it.

Extra resources

Here are some useful links that didn’t make it into the main text:


Quite a few people provided feedback and help at various stages of the writing, including: Gregory Yang Kam Wing, Kushaan Shah, Rishi Dhanaraj, Tamara Scott, Kritika Sony, Alicia Kenworthy, Tom White, Daniel Hightower, Dan Stern, Liz Koblyk, James Quiambao, Kyla Scanlon, and Nivi Jayasekar. This list may not even be exhaustive!10let me know if you gave me feedback and I committed the egregious error of forgetting you 🙁


Leveling Up the Skill of Friendship: The Why

Says the popular adage:

Give a man a fish and you feed him for a day.

Teach a man to fish and you feed him for a lifetime.

Teach a man to make friends and now all his fisherman buddies give him freshly caught fish whenever he visits them down by the pier, plus they water his plants when he’s out of town, plus they help him pull through when he’s feeling down, plus he’s also friends with the bakers so he gets fresh BREAD in addition to the fish.

At the risk of stating the blindingly obvious, friends are great. Almost any relationship, including romantic or professional ones, is better when it involves friendship.

But friendship isn’t necessarily easy or natural. Everyone is somewhere between good and bad at it.

Friendship is, in fact, a skill. Even if we rarely think of it as one.

And unless you’re especially talented, or unless you’ve deliberately practiced, there’s a reasonable chance that you’re not as good at friendship as you could. Yet there may not be a skill worth mastering more, as the (totally authentic) proverb above illustrates.

This is an introductory essay in what I expect to be a series of posts on friendship. Here, we’ll discuss the “why”: why friendship is a skill, and why it’s an important one. At the end, we’ll briefly lay some groundwork for another essay about the “how.”

But first, a personal anecdote.

An auction of dreams

In the Quebec secondary school system, there used to be a class called “Personal and Social Development.” It was a hodgepodge of sex education, ethics, and other things neither I or my high school friends can remember.1though many of us remember that time the teacher brought a chocolate cake made with mayonnaise, which seemed like a mind blowing idea at the time.

One of the few things I do remember from that class was the “auction of dreams” we had once. The teacher would read out some ambitious life goals, like “to become the prime minister,” and we would bid points to buy them. The one dream I won was “to have a true friend.” I didn’t need to spend a great deal of points for it; my classmates seemed less interested. Perhaps because, to them, it felt more ordinary than the other dreams, or more easily attainable.

But I knew that making new friends was, for me, a slow process. That deep, true friendship was rare. I wasn’t (and am not) disastrously bad at social skills, but I’ve always felt a bit below average, just enough to often be somewhat dissatisfied with my social life. I regularly wish I were part of some cohesive community of friends.

In the narrative of my life, that auction of dreams has become a defining moment. A sign I knew I was slightly inadequate at something very important.

Usually, though, I’m doing just fine. “Usually” as in “when there isn’t a horrible virus floating around and forcing us to cancel so many of the good things in the world.” The pandemic contact restrictions feel as if someone had detonated dynamite in the fragile social life that I had been slowly and painstakingly growing for years. It’s not that I’ve lost friends. But all the contexts — work, organized activities, parties — in which we effortlessly and serendipitously spend time with people are now gone. Social interaction has become more intentional. It takes more energy.

So I’ve been sitting at home, wondering how to save what I could, and how to efficiently rebuild my social life. Then I happened upon the work of Visakan Veerasamy, better known as Visa. If your Twitter is anything like mine, you’ll know who I’m talking about. He’s all over the place.

Visa’s mission is “to build the greatest social graph of friendly, ambitious nerds that the world has ever seen.” As he writes in his book Friendly Ambitious Nerd:

Friendliness​ is about being a nourishing presence. It’s about becoming somebody who people (including yourself!) love and enjoy. It’s about creating supportive, encouraging spaces where people can feel comfortable sharing their honest feelings. Humans are a social species, we’re practically wired to desire kinship, to be part of something bigger than ourselves. So why not get good at it?

Yeah, why not? Why not see it as a skill, as something you can learn and master?

You can be good or bad at basic human needs

I can think of a few reasons why friendship is rarely framed as a skill.2It’s more common to talk about “social skills,” but my view is that this is both more general and less important than just friendship. One is that almost everyone picks it up to some extent in their youth, usually in school. Another is that socialization is a basic human need. So we learn the art of friendship the same way we learn the art of eating: as a necessity for survival.

But even a basic need like eating involves several activities that we can be good or bad at: selecting foods to buy, meal planning, cooking, picking a restaurant, finding a balanced diet, and even just enjoying what you eat.3Some people apparently never enjoy their food, and eat for sustenance only. For an example, read the beginning of this Slate Star Codex piece.

Similarly, the skill of friendship comprises a bunch of things we can be good or bad at:

  • making new friends
  • keeping in touch; general friendship maintenance
  • providing support and value to friends
  • moving from a superficial to a deeper friendship
  • managing conflicts and unhealthy dynamics
  • ending a friendship, as we sometimes must.

Even though most people learn to do most of these things from a young age, there are signs that we’re not, collectively, that good at them. Many people are lonely, and the media regularly mentions a “loneliness epidemic” (it’s unclear that there really is such a thing, depending on whether you focus on subjective perception of loneliness or increased atomization, but the fact that we worry about it is telling). It’s not uncommon to hear friends say they “haven’t been a good friend” when you talk to them for the first time in a while. And it has become trite to state that “it’s hard to make friends as an adult.”

Of course, there are many reasons why it can be hard to make friends, or why we feel socially isolated. Lack of skill perhaps shouldn’t be seen as a cause. But surely becoming skilled at the items in the list above can be an antidote.

Now, is it worth our time, relative to other skills we could learn?

Friendship as magic

What are friends good for?

I don’t think I really need to enumerate this. But let’s do it anyway.

There is the mundane: having your fish fed when you travel, borrowing stuff you need. There’s everything related to mental wellbeing: staving off loneliness, feeling important, getting emotional support when things fall apart. And then there’s what we like to call “networking”: finding jobs, ideas, projects, things to learn, people to meet, and more friends.

Friends are also shortcuts to skills you don’t have — like fishing. It’s more common to get these shortcuts through commercial transactions, of course, by trading some skill you have for money and then trading the money for someone’s services. But friendship provides a second way to “cheat.” It can even be the skill that earns you a living, if you’re especially good at it — through sales or community organization, for instance.

One cool way of describing the benefits of friendship is in terms of luck. Luck is a word we use to describe the good things that unexpectedly happen to us. Unlike what you may think, it’s  perfectly possible to increase your luck. You simply have to expose yourself to as many situations with potential good outcomes — new opportunities — as you can.4I was reading Antifragile by Nassim Taleb as I was writing this piece, and it sounds like Taleb would call this “optionality” as opposed to luck. You increase the probability of a good outcome by giving yourself more options, especially those with more potential upsides than downsides. I’m okay with calling this luck.

And what better way to do that than interact with lots of people who like you?

So friends can provide you with material benefits. They can replace the need to learn some skills. They allow you to manipulate luck. And they do all that while making you feel great.

Life skills don’t get any more magical than that.

logo of My Little Pony: Friendship is Magic

right, I knew I’d seen this idea expressed somewhere before

Towards the how

Okay, so how do we master the skill? How do we get better at making new friends, managing friendships, being a good friend, and dealing with the unfortunate uglier parts?

This question deserves a full essay, and one that I’m planning to write very soon. (Feel free to subscribe if you don’t want to miss it.)

The central point, however, is clear. To be good at friendship, you need to be a valuable person to your friends. You can be valuable in many ways, but most boil down to two main qualities: be kind, and be interesting.

To be kind is to care about the people around you. To remember their names and birthdays. To be there when they need help. To apologize when you’ve wronged them. To have empathy.

To be interesting is to bring value to your friends. To teach them things. To bring them new encounters and opportunities. To be a good conversation partner. To nourish their minds.

How can we get better at being kind and interesting? How do we level up the skill of friendship? There are many paths. But the first step is to realize that it is a skill.


Many thanks to the amazing people who read drafts and provided feedback: Gregory Yang Kam Wing, Sarah Boudreault, Rhishi Pethe, Carolina Perez, Padmini Pyapali, Alexander Hugh Sam, Charlene Wang, Sachin Maini, Nivi Jayasekar, Snigdha Roy, Mohammed Malik, Tom White, Alicia Kenworthy, Kritika Sony, and Christian Keil.