Stop trying to have "interesting" friends

friendships as vehicles for aspiration

Jo-Ann Acey, Valley Dream, 2022

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.

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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.¹

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.²

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.

that’s it, that’s the whole meme.

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.

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So stop looking for interesting friends³. 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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Thanks to Manansh for reading drafts and helping me think about this topic.

1. https://www.3-16am.co.uk/articles/aspiration

2. https://www.econtalk.org/agnes-callard-on-aspiratio

3. You should also eliminate the word “interesting” from your vocabulary. Not just because it’s holding you back in your friendships, but because it’s a lazy word all-around. “Interesting” has become a crutch to disguise a lack of precision and thoughtfulness with the words we use. I can’t remember the last time I said “interesting” and actually meant interesting.