Originally published on substack: https://eliqian.substack.com/p/stop-trying-to-have-interesting-friends

Within the tech and tech-adjacent circles I’m part of on the internet, a number of essays and tweets have been making the rounds about what makes someone a person you want to spend time with.

This is definitely a worthwhile question to answer. So much of our life experience is colored by the people we share it with. However, there is a concerning amount of emphasis on having friends and seeking out people who are smart, thoughtful, and (the worst one of all) “interesting.”

The obsession with interesting makes me uneasy. Friends aren’t resources for intellectual stimulation or new insights. I don’t want my friends to like me because I read niche blogs or have things to say about crypto. It comes dangerously close to conflating knowing a lot, reading a lot, or having thoughtful things to say with moral goodness. (Worth noting that interesting isn’t a negative trait. I would prefer my friends to be interesting, but it feels superficial to prioritize it.)

If I think about what kind of person I want to be close friends with—my best man at my wedding, people I would do anything for, the ones I can rely on when I’m at my lowest—smart and interesting really aren’t front of mind.

On top of that, it doesn’t feel right to pressure people to be “interesting” in your sense of the word. Everyone is interesting. Every person in the world has a literal lifetime of experiences that have shaped who they are. They have internal thought processes and distinct worldviews that you won’t find within anyone else. It’s a matter of giving your interactions enough time and care to discover these.

You shouldn’t feel obligated to be friends with everyone or pressured to get along with all people, but “interestingness” is a poor heuristic for finding genuine connection. It’s time we realign our priorities and recognize that our preoccupation with being interesting is symptomatic of a flawed view of friendship.

Ava of Bookbear Express made an observation I think about often:

It’s not about what you find intellectually cool, or what seems like the best “opportunity.” Those things can be important too, but they don’t matter if you hate doing the thing…

You have to do the thing you actually enjoy doing, not the thing you find conceptually exciting.

It’s easy to convince yourself you get along with someone because you like the same books or because they’re extremely perceptive in conversation. You can be intellectually stimulated when you spend time with them, but the feeling of leaving a thoughtful conversation is qualitatively different than the feeling of returning from a night of karaoke.

There is intellectual fun, and there is fun—old-fashioned, forget about the world, I could do this forever type fun. You might think you could spend the rest of your life debating AGI, but you’d be missing out on the fun that lets you surrender to life.

There’s a tendency to romanticize and overrate relationships with intellectually compatible people because we can clearly imagine how they play out. We can see how the other person might make us more thoughtful and inspired. We have ideas and fantasies of the person we’ll become after years of friendship.

But for friends we have old-fashioned fun with, it’s harder to see the evolution. We can imagine having a good time, but it feels like eating junk food—great in the moment, but not contributing to our long-term goals. This is wrong and short-sighted.

When have you felt most alive? What moments have changed you? The moments that come to mind often arrive in unexpected ways. If I think about my favorite (and most meaningful) interactions, they’re rooted in the emotional rather than intellectual. We attach more meaning and weight to moments that deliver raw, limbic resonance. The stuff of hearts, not minds.

Aspiration and ambition

The obsession with interestingness comes from a model of friendship that views friends as vehicles for ambition: you have an idea of what you want out of life, and friends are chosen with those priorities in mind.

An alternative view is that friends are aspirational. You know you will change and grow, you acknowledge you don’t know for certain where you’re going, and your friends are the people you most want to share that journey with.

This is all pretty woo-woo and hand-wavey, so here’s Agnes Callard to clarify the distinction:

Ambition is the process of improving one’s lot by making a large change whose value one fully grasps in advance. It aims to satisfy desires rather than to acquire desires.

Prioritizing interestingness makes sense if you view friendship closer to the ambition end of the spectrum. You have an existing value system and friends are selected to maximize whatever utility function you’ve decided on.

The thought process might go something like if I curate my friends and optimize for smart/thoughtful/interesting then my life will be richer with the ideas and interactions I care about.

For example, you might want friends to:

  • Inspire you to be more ambitious because you value doing big things and having an impact on the world
  • Make you think deeply about topics because you value intellectual curiosity
  • Teach you about things because knowledge in those areas contributes to your goals (career, personal, whatever)

Notice, these are not bad things. You could do a whole worse than seek out people who inspire you and teach you new things. But what if we viewed friends as more aspirational?

Aspiration, according to Callard, is “the process of value acquisition.” It’s how we learn to see the world in new ways:

If you just think about most of the things that you value right now, like in relation to your career, your kids, some hobbies you have, some of your, like, political values or ideology—if you just go back far enough, there'll be some point in your life when you didn't value those things…

Aspiration is how you got from there to here. How you came to care about the things that you care about.

Rather than curating friends based on our first-order values, our friends are ways to develop our values and how we see the world. And I don’t mean through emulation, but just from sharing experiences. So instead you might want friends who:

  • Will make every effort to be there at important moments in your life
  • You trust deeply and feel comfortable sharing with
  • Instinctively ask you to join them in whatever they’re doing

It’s difficult to visualize how these friends will make our lives richer because they end up shaping how we see the world. Today, there are things you value that you didn’t 10 years ago. What you consider the “good life” today is different than a decade ago. Your idea of thriving back then might be a bleak existence today.

This view acknowledges that there is more to friendship than what can be gleaned for our immediate goals and that sometimes people can influence us enough to fundamentally change who we are.

This comes closer to the core of my aversion to interestingness. Prioritizing it feels cold and arrogant. To be so sure about something so complex and nuanced as what you want to value in life. It doesn’t leave room for you to be completely and utterly wrong about something core to who you are.

A new north star

Given all of this, what should we look for in friends? What is a better north star to guide our relationships?

One thing I keep coming back to is open-mindedness. I’m drawn to people who don’t take themselves too seriously. People who move through life with a certain nonchalance that makes them eager for the unconventional and unusual. These people can laugh about anything and like to have fun.

Something I appreciated when living in Austin was my friends’ willingness to do anything at any time. Basketball until 1am? Yeah, we got five. Someone wants to go to happy hour? There’s a group ready to join you. I remember us discussing a Super Bowl watch party literal hours ahead of kickoff. Nothing was planned yet, but there was never a doubt that we would get something going.

These friends expand our boxes of possible experience. Spontaneity and unconstrained eagerness feel good because they are exercises in doing without thinking too much. Having the thought I want to do this, and then immediately being able to do the thing with people you care about silences the voice of “reason” in our heads.

When we surround ourselves with open-minded people, we are able to live the life of our intuition. We act on what feels right before we can convince ourselves otherwise.

Without these people, we rationalize reasons to stay in the comfort zone. We limit our aspirational opportunities and we never give ourselves the chance to have our minds changed and our world opened up. Far more than the ability to talk deeply about a Substack essay, write code to solve difficult problems, or ask thoughtful questions, we should value the people who stop us from turning our instincts into unmade decisions.

So stop looking for interesting friends. Actually, it might be the best move to ignore everything I’ve written up to this and give up the idea of seeking out an archetype of a person or even specific traits or indicators. The premise that we can intellectualize and hack our way to the most meaningful friendships is, very likely, misguided.

Socialization is a really fundamental part of the human experience. We’ve been doing it for hundreds of thousands of years. Maybe we weren’t meant to think too hard about what goes into a good friendship. Maybe thinking is simply the wrong tool for the job. We don’t need words, precise concepts, or standardized signals for friends we like in order to identify them.

For all the people who have written about what goes into making a person magnetic or attractive as a friend, putting words to a feeling doesn’t make the feeling any more real. You’ll still know when you just click with someone, and you’ll still experience the highs of friendship even if you don’t realize why.

On the spectrum of a calculated search for friends to an unconditional acceptance of people, we might all do better to lean the other way.

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15 comments, sorted by Click to highlight new comments since: Today at 7:40 PM

I think I'd be more comfortable with this (as with much social and cultural "advice" discussions) if it were framed in the positive, not the negative, and if it acknowledged that friendship is complicated and diverse, with multiple distinct reasons for making and keeping friends, not all of which will (or should) apply to all your relationships.  One reason this bothers me is that it advises a directional change "stop trying" without specifying how to decide on the right level of trying, and noting that SOME readers might want to try a bit more to cultivate interesting friends.

I think part of your message is "think of friendship as somewhat illegible, with many of the benefits hard to measure, and therefore recognize that a strict cost-benefit analysis will be very misleading".  I fully agree with this.  Part of your message seems to be that interesting and intellectually stimulating are not worthwhile traits, and I rather disagree with that.  

Friends aren’t resources for intellectual stimulation or new insights. I don’t want my friends to like me because I read niche blogs or have things to say about crypto. It comes dangerously close to conflating knowing a lot, reading a lot, or having thoughtful things to say with moral goodness.

I think I would reverse most sentences in this paragraph. Being able to think for yourself and have your own useful and insightful takes on how the world is working seems to me closer to a requirement for being able to take morally good action. Anything can be goodharted, but it doesn't mean that we should believe that there is an inverse correlation.

One thing I keep coming back to is open-mindedness...

Something I appreciated when living in Austin was my friends’ willingness to do anything at any time. Basketball until 1am? Yeah, we got five. Someone wants to go to happy hour? There’s a group ready to join you. I remember us discussing a Super Bowl watch party literal hours ahead of kickoff. Nothing was planned yet, but there was never a doubt that we would get something going.

These friends expand our boxes of possible experience. Spontaneity and unconstrained eagerness feel good because they are exercises in doing without thinking too much.

This seems like a fine thing to look for in a friendship, and I agree that open-mindedness is a positive trait. I would definitely object to "spontaneity" being a core part of what "we" should all want as a "north star". I think there's a strong current here of "lots of experiences" which many people don't want (as opposed to a simple and steady life). I think having your best interests at heart, moral virtue, reliability, and a bunch of other things can be good without the spontaneity aspect, so I don't think it's something that all people should want.

(No coherent theory of friendship, just thinking out loud.)

Seems to me that there are two aspects of friendship to consider:

  1. One needs allies. We need someone to help when we get in trouble. We need someone to do various activities with. Even if we do not literally "need" someone, it often feels better to have someone.
  2. Humans instinctively copy their friends. Conversely, your openness to copying someone will probably set a limit to how friendly you can get with them.

To put it shortly, you friends will help you, and they will change you. (And vice versa.)

The first one would suggest that you should have as many friends as possible, but there is a limit, because you need to spend time and energy cultivating the friendship: meeting your friends, helping them, etc.

Talking about "friendship" can be confusing, because we use it to refer to different intensities of relationships. Or we can use different words for different intensities, such as "acquaintance"; but different people do not use these words consistently. Extraverts probably need more friends than introverts. Different people can be differently calibrated, because of different life experience. (For example, if your life is all fun, you probably focus on the "fun to be with" part of friendship, and ignore the "help each other when needed" part.) If you are attractive, cultivating friendships may seem unnecessary, because you can always easily make new ones. If you really suck at connecting with new people, you may overestimate the value of the friendships you already have; maybe the people you call friends are actually just using you.

...so it makes sense that different people have different theories of "friendship".

(Plus there is the usual human unconscious hypocrisy. Maybe you find it morally repulsive to choose your friends based on how instrumentally useful they are, and you are looking for fun and connection on the spiritual level instead. And yet, somehow, the people you connect with spiritually all just happen to be somehow useful to you. And the ones who stop being useful, you suddenly find less fun, and the spiritual link soon breaks...)


From the perspective of making allies, what is the value of "interesting" friends? First, they are useful instrumentally (literally: they do something that interests me). Second, to be "interesting" can be a proxy for social skills, intelligence, high status, and other qualities desirable in an ally.

What is the downside? Well, am I sufficiently interesting myself? If not, that is, if I am trying to make friends with people who are significantly smarter or more popular than me, chances are that they will not be interested, or that the result will be a painfully asymmetric relationship (e.g. the kind of relationship where you always do various things for your friend, but you friend is always too busy to help you). It would have been better to select friends e.g. between people who share the same hobby, because there the thing that makes them more interesting to you, happens to be the thing that also makes you more interesting to them.

From the perspective of copying, the question is whether the thing that makes the person "interesting" can really be copied. Because, some traits cannot be copied; most obviously, hanging out with tall people is not going to make you any taller (unless their secret is wearing high heels, and as a friend they will let you in on the secret). More controversially, what about rich people? I bet someone like Kiyosaki would argue that hanging out with rich people will let you unconsciously copy all the secrets of highly successful people. But what if you are kids, and the only secret is simply to be born to rich parents? You can't copy that! More likely, you will copy the habit of spending money, which may actually make you poorer. (Why do I mention rich people in a comment about interesting people? Because being rich is one way of being interesting. You certainly have more time and opportunity to do interesting things, compared to e.g. people who need two boring jobs to pay their bills.)

On the other hand, if someone is interesting because they e.g. can juggle well, hanging out with them is a good way to become interesting yourself.

You can side-step the issue if you limit 'friends' to a more restrictive subset.

i.e. those who are both worthy allies and worthy of emulation.

(Personal anecdote, this is the internal definition I had growing up so I was continuously mystified by folks claiming they made dozens of friends in high school, college, etc...)

But the downside of this method is that some people could literally go their entire lives without a single 'true friend' which may cause problems of communication somewhere down the line.

People can generally tell when you're friends with them for instrumental reasons rather than because you care about them or genuinely value their company. If they don't at first, they will eventually, and in general, people don't like being treated as tools. Trying to "optimise" your friend group for something like interestingness is just shooting yourself in the foot, and you will miss out on genuine and beautiful connections. 

But sometimes something happens in the world and your "best man always fun forever" friends can't seem to understand reality. They think it's because God wanted it this way or because there is a world wide conspiracy of Jews. Then you feel really alone.

That sucks. I lost a good friend like this. He discovered religion, and... I hoped we could just "agree to disagree" on this topic, and talk about the many things we still had in common. Instead, he was even more annoying than all other religious people, because he assumed that he knows exactly how I think (he kept saying he also used to think the same way before he found Jesus) so he can show me the way. And he couldn't stop bringing up the topic. He became completely insufferable; we stopped interacting completely.

(For the record, I do have a few friends who are religious or have other beliefs I don't share. The trick is, they are not trying to convert me. We discuss other things. Heck, we can even discuss religion, if they accept I am only doing it the same way I would discuss Tolkien.)

When this happens, it's time to find new friends. Or maybe pay more attention to old low-intensity friends; sometimes the opposite thing happens and you find out that as you grew up, you have more in common.

Not necessarily a bad thing. This has happened to me a few times with childhood friends, especially in our 20s, and we've usually reconnected as beliefs have changed or we consciously decided that any disagreements we have simply make for good conversation.


If you're wealthy, in some elite intellectual class and social strata by virtue of your academic or professional credentials, the people with whom you end up forging these organic, valuable friendships end up being those who are more interesting, intellectually stimulating, etc. There's a certain stochastic privilege afforded to those who can approach building friendships and relationships in this carefree, feel-good, fun-maximizing way and still end up with much more interesting, high value, intelligent friends. You get to have your cake and eat it too.

If you're not well off, of a low status and removed from the power-centers of the world intellectual elite, you couldn't get such high chances associating with people in a natural, carefree way. You'd have to be directed, focused and deliberately agentic towards cultivating a high-value social circle bearing all the accoutrements of being interesting enough to match your criteria.

You can make good friends anywhere, but you could still manage to make interesting friends the "right" way (according to this post) by just relocating to places where the type of person you'd prefer to associate with, with respect to their intellectual/personal merit, is more common, and let the friendships develop naturally.

Somehow this reminded me of an advice to women: "Do not marry for money; you will be unhappy. Instead, select your environment so that you only ever meet rich men... and then marry for love."

It comes dangerously close to conflating knowing a lot, reading a lot, or having thoughtful things to say with moral goodness.


Take note however, that life is generally short, and stakes of friendship are high. Interesting, knowledgeable personality is not equal with moral goodness, but it strongly correlates with at least, being more beneficial than harmful. It also strongly correlates with open-mindedness, and usually with empathy (since, part of empathy is being able to emulate the thought processes of another person within your mind, to guess their possible reactions, and that takes raw intelligence). 

Or to put it differently: Interesting Friends are more likely to be Good Friends than Bad Friends. Non-Interesting Friends are slightly more likely to be Bad Friends, or that you would be a Bad Friend to them out of boredom.

So, given that we are unlikely to be able to acquire dozens upon dozens of friends to test, or invest equally in everybody around us, it makes more sense to invest in Interesting Friends, then test them for things like conscientiousness, ethics and open-mindedness.

(Note: we should also consider neurodiversity issues. An Interesting Friend is significantly more valuable to a person with ADHD. A perfectly morally upright and open-minded Friend who is nevertheless Boring, would make an ADHD person claw their own brain out in frustration. TO put it differently, people's tolerance of Non-Interesting/Boring people range from "eh, he's alright" to "hanging out with them is a Cruel and Unusual Punishment".)

i’d love for anyone to present the argument against this. eq says it’s things like karaoke which make friendships great. the friends i know who are eager to do karaoke are the same ones who will start wild, speculative conversation when we’re idly sitting in the living room together. they’re the interesting people.

the people in my life whom, come the first lull in smalltalk after dinner get uncomfortable and declare “great meal, time to go” instead of opening themselves up for those late-night intimate conversations, are the same people who would turn down an invitation to karaoke.

interesting friends are fun friends. “boring” is the opposite of both “fun” and “interesting”. so if the latter two mean something different to the author than to me, perhaps we agree by saying “build non-boring friendships”?

I guess, as a first approximation, any unusual hobby selects for open-mindedness.

my hunch is that we naturally segregate into monkeyspheres where certain definitions of interesting basically equal fun for everyone involved, and the Boring people are basically strangers, breaking the flow. Moreover, humans are not that different, we tend to be interested in similar things, and tend to be bored with similar things, at least broadly speaking.

What I think OP is trying to tell us, is that we should not over-focus on superficially fascinating snobs, who talk good game but aren't good friends, but I think most people actually know that; we treat our brief interaction with Superficially Interesting People the same way we treat chocolate, wine or weed: its fun to have a little every now and then, but we're not building our lifestyle around it.

Great post! I've linked to it from the EA Lifestyles substack. https://substack.com/profile/127787889-ea-lifestyles/note/c-14971201