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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


Introduction

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.

Epicurus

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.

Online

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:

Acknowledgements

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 🙁

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