Intentionally Making Close Friends - LessWrong

make-public

One of the core parts of my life philosophy now is the skill of agency, of actually doing things. The skill of going out of your way to make opportunities. To identify what’s missing in my life, and in the world. Finding the actions that I don’t need to take, that no one else will make me take, or do for me, and deciding to take them anyway. Fixing that which is broken. Finding that which is not broken, and deciding to make it better anyway. Exploring and trying new things. Challenging my self-image and growing. Fundamentally escaping the mindset of needing permission, and breaking past the illusion of doing nothing. I think this is one of the most valuable skills anyone can learn, and one I cherish, though I am far from perfect at it. And this experience is a large part of why I value it. Not realising I could make close friends was a failure of agency, an unknown-unknown that cut out a massive amount of potential happiness, without even realising it.

questions to induce emotional connection

One of the main reasons I’d recommend others try this is that it broke me out of a bad equilibria. I was trapped in a ‘normal’ mode of conversation - making small talk, being inoffensive, feeling aversion to being weird, respecting where I thought other people’s boundaries were. But when I tried something totally different and super weird, it often went great! Sometimes other people hate small talk too, and also seek a genuine connection. But by default, this would never have happened - it took one of us taking initiative to break past the trap of social norms. And only by having a bunch of unusual and scary conversations yet having them go great did I develop the courage to be weird.

Seek excitement

A tactic I find helpful here is what I call recursive curiosity.

Sometimes I feel trapped in a boring conversation direction because the structure of small talk feels hard to break out of. When this happens, I like to go meta, eg observing ‘man, I feel like I keep having the same kinds of conversations at these places’ or ‘let’s get the boring questions out of the way - [standard small talk done rapidly]’. If they seem to empathise, this is a good opener for a more fun question, eg: ’what kind of things do you get excited about?’, ‘what’s something cool you learned recently?’, or ‘have you had any particularly memorable conversations in [this context]?’

My main approach is to create a space in which it feels safe to be vulnerable, but try to avoid creating obligations. I try to be honest and vulnerable myself, and freely share things that feel authentic throughout the conversation. I prefer to express lots of small vulnerabilities throughout the conversation rather than sharing something major and making it feel like a big deal - the latter tends to create an obligation/expectation of reciprocation, while the former better establishes a ‘I consider this fine and normal’ norm. I also find that both are effective for breaking people’s social scripts/default ways of acting by being weird and unexpected - I find this is often a good first step to actually having a meaningful conversation. I find that sharing anxieties and insecurities can work particularly well here - almost everyone has them, it feels stigmatised to discuss them but people tend to respect you when you do, and they’re often much more common and relatable than people think. I’ve had a bunch of these conversations, and still find it exciting (and sad) when I meet someone with really similar problems to me! vulnerability

Personally, I tend to be very anxious about whether I’m making other people uncomfortable, so I find this technique pretty aversive at times. My main approach to motivation here is internalising that I want to be a person who actually does things - that being vulnerable and welcoming vulnerable are skills I find uncomfortable but value, and I am growing as a person if I cultivate them. And, empirically, I’ve found this really useful to practice. I find this often leads to really awesome interactions, often in my first interaction with someone.

Thus, if I am meeting new people and want to find potential close friends, I want to filter fast for compatible people. Further, compatibility is heavy-tailed - I won’t really vibe with most people, but some people are awesome. I want to explore and optimise for information. This pushed towards high-variance strategies. If I meet 100 people, and want to pursue a friendship with just a handful, this is great! This is a very, very different mindset from standard social norms, which push me towards being bland and inoffensive, and minimising the probability of bad interactions. A bad interaction (so long as it doesn’t damage my reputation) is just as useless as a mediocre interaction for finding potential friends. Instead I want to maximise the probability that, if someone is compatible with me, we have an awesome interaction. This is a key part of why I push for excitement and vulnerability - many people won’t vibe with that, but it makes it much more likely that I hit it off with the right kind of person.

Further, I am not constrained by the number of people I could meet - there are a lot of interesting people in the world. This means it’s OK (but sad) if some people I could be compatible with don’t vibe with my approach. Some people are pretty closed at first, and take a while to warm up to new people, but are awesome once this happens - my strategies around eg minimising small talk work much less well on this kind of person, which is sad. But the ability to filter fast is crucial

Another key part of hits-based befriending is meeting lots of people, and exposing myself to lots of possible hits. sourcing

A key second step to the hits-based befriending mindset is to follow-up once I identify someone cool! I try to make sure I get their contact info, and reach out shortly after meeting them trying to arrange a call/meetup. I find that many people are too socially anxious to do this, but this is a really useful skill to practice. The vast majority of my current friendships would not exist if I was bad at reaching out. Most people find this great and flattering, don’t overthink it.

Another tactic for overcoming anxiety is to other-ise. Imagine you met someone at a party, they thought you were cool, and messaged you afterwards asking to meet up again. I don’t know about you, but I’d find that pretty flattering. Or, imagine a specific friend coming to you with an analogous situation, asking whether they should follow-up. What advice would you give to the friend? And, if it differs from your internal thoughts about your situation, why? Personally, I have yet to find a situation where the advice I give to the friend is worse than the advice I give myself.

A related and important skill is keeping in touch. Most people are really bad at keeping in touch, especially without a structure like university that keeps you in frequent contact. This means that many friendships fizzle without this structure. And this is really sad! I find a common mindset is ‘if friend X really valued this friendship, I wouldn’t be the one to always reach out’. But, empirically, I am confident many of my friends value our friendship, but also suck at reaching out. Being conscientious and organised is just hard

For me, much of the anxiety around follow-up and keeping in touch centre on being a burden, and bothering other people.

Relatedly, have good and clear communication about what we both want out of the friendship, and how the other person adds to our lifePeople often find this hard - it’s hard to eg communicate about ways the other person annoys you without harming them. For me, a key is creating clear and explicit common knowledge that we both value this friendship and are invested in it. This frames all clear communication as being on the same team - we’re trying to work together and share information, so we can both forge a better friendship

Exercise: Make a list of your good friends. Which of them do you feel closest to, and what has led to this? What blocks are there to being closer to some, and what are you going to do about it?

One of the core parts of my life philosophy now is the skill of agency, of actually doing things. The skill of going out of your way to make opportunities. To identify what’s missing in my life, and in the world. Finding the actions that I don’t need to take, that no one else will make me take, or do for me, and deciding to take them anyway. Fixing that which is broken. Finding that which is not broken, and deciding to make it better anyway. Exploring and trying new things. Challenging my self-image and growing. Fundamentally escaping the mindset of needing permission, and breaking past the illusion of doing nothing. I think this is one of the most valuable skills anyone can learn, and one I cherish, though I am far from perfect at it. And this experience is a large part of why I value it. Not realising I could make close friends was a failure of agency, an unknown-unknown that cut out a massive amount of potential happiness, without even realising it.

What’s the best way to get to know you as a person? What’s your life story? What traits do you envy/value in those around you? What do you feel insecure about? This one is higher variance - I don’t recommend leading with it! What do you value in friendships? What are the best ways they add to your life? How, historically, have you become close to people? If you could design a personal set of social norms for how your friends interact with you, what would they be? How would other people describe you? How does this compare to how you want to be perceived? What in life do you get truly excited about?

One of the main reasons I’d recommend others try this is that it broke me out of a bad equilibria. I was trapped in a ‘normal’ mode of conversation - making small talk, being inoffensive, feeling aversion to being weird, respecting where I thought other people’s boundaries were. But when I tried something totally different and super weird, it often went great! Sometimes other people hate small talk too, and also seek a genuine connection. But by default, this would never have happened - it took one of us taking initiative to break past the trap of social norms. And only by having a bunch of unusual and scary conversations yet having them go great did I develop the courage to be weird.

Seek excitementA key mindset I use when forming connections via conversation is: “If we aren’t both excited about this conversation, do something differently”. This applies especially when talking to someone I don’t know well, and want to figure out whether we might become good friends. Most social norms optimise for conversations that feel safe, not ones that feel exciting, so I need to do something differently! This means asking the other person questions. This means taking a genuine interest in what we’re talking about - and if I can’t take a genuine interest, then I am doing something wrong.

A tactic I find helpful here is what I call recursive curiosity. I lead by asking an open-ended question that invites a detailed answer. Then, I introspect and try to notice excitement, find the part of their answer I find most interesting, and ask a follow-up open-ended question about it. Then, I repeat this process on their new answer. After about 3-4 iterations, we’ve normally gotten somewhere that feels alive and novel, where we’re both learning, rather than the same stale conversations they have all the time. The follow-up questions don’t need to be thoughtful or elaborate, often just ‘[specific detail] sounds interesting, tell me more’ or ‘[specific detail] didn’t really make sense to me, can you clarify? Did you mean [naive interpretation]?’ are more than enough. Introspecting on confusion or curiosity also works well. Often, rather than having a clear purpose to my questions I try to maximise surface area - just asking questions that point at my confusions and try to maximise the new information I gain, and the amount that I learn. This tends to feel fairly reactive - just responding to whatever was most interesting in the last thing said.

Sometimes I feel trapped in a boring conversation direction because the structure of small talk feels hard to break out of. When this happens, I like to go meta, eg observing ‘man, I feel like I keep having the same kinds of conversations at these places’ or ‘let’s get the boring questions out of the way - [standard small talk done rapidly]’. If they seem to empathise, this is a good opener for a more fun question, eg: ’what kind of things do you get excited about?’, ‘what’s something cool you learned recently?’, or ‘have you had any particularly memorable conversations in [this context]?’

My main approach is to create a space in which it feels safe to be vulnerable, but try to avoid creating obligations. I try to be honest and vulnerable myself, and freely share things that feel authentic throughout the conversation. I prefer to express lots of small vulnerabilities throughout the conversation rather than sharing something major and making it feel like a big deal - the latter tends to create an obligation/expectation of reciprocation, while the former better establishes a ‘I consider this fine and normal’ norm. I also find that both are effective for breaking people’s social scripts/default ways of acting by being weird and unexpected - I find this is often a good first step to actually having a meaningful conversation. I find that sharing anxieties and insecurities can work particularly well here - almost everyone has them, it feels stigmatised to discuss them but people tend to respect you when you do, and they’re often much more common and relatable than people think. I’ve had a bunch of these conversations, and still find it exciting (and sad) when I meet someone with really similar problems to me!

Personally, I tend to be very anxious about whether I’m making other people uncomfortable, so I find this technique pretty aversive at times. My main approach to motivation here is internalising that I want to be a person who actually does things - that being vulnerable and welcoming vulnerable are skills I find uncomfortable but value, and I am growing as a person if I cultivate them. And, empirically, I’ve found this really useful to practice. I find this often leads to really awesome interactions, often in my first interaction with someone.

Thus, if I am meeting new people and want to find potential close friends, I want to filter fast for compatible people. Further, compatibility is heavy-tailed - I won’t really vibe with most people, but some people are awesome. I want to explore and optimise for information. This pushed towards high-variance strategies. If I meet 100 people, and want to pursue a friendship with just a handful, this is great! This is a very, very different mindset from standard social norms, which push me towards being bland and inoffensive, and minimising the probability of bad interactions. A bad interaction (so long as it doesn’t damage my reputation) is just as useless as a mediocre interaction for finding potential friends. Instead I want to maximise the probability that, if someone is compatible with me, we have an awesome interaction. This is a key part of why I push for excitement and vulnerability - many people won’t vibe with that, but it makes it much more likely that I hit it off with the right kind of person.

Further, I am not constrained by the number of people I could meet - there are a lot of interesting people in the world. This means it’s OK (but sad) if some people I could be compatible with don’t vibe with my approach. Some people are pretty closed at first, and take a while to warm up to new people, but are awesome once this happens - my strategies around eg minimising small talk work much less well on this kind of person, which is sad. But the ability to filter fast is crucial

Another key part of hits-based befriending is meeting lots of people, and exposing myself to lots of possible hits. Some of my favourite approaches:Going to meetupsGoing to events that will attract people with similar interestsTalking to people around me in talks/lecturesAsking my friends for intros to their friends - both generically (‘do you know anyone I might get on with?’) and specifically (‘can you introduce me to [specific person]?’)Proactively reaching out to people who seem interestingI find this pretty anxiety-inducing, but it has a surprisingly high success rate. Most people are flattered!Having public forms on my website for people who want to have a chat or go on a date

A key second step to the hits-based befriending mindset is to follow-up once I identify someone cool! I try to make sure I get their contact info, and reach out shortly after meeting them trying to arrange a call/meetup. I find that many people are too socially anxious to do this, but this is a really useful skill to practice. The vast majority of my current friendships would not exist if I was bad at reaching out. Most people find this great and flattering, don’t overthink it.

Another tactic for overcoming anxiety is to other-ise. Imagine you met someone at a party, they thought you were cool, and messaged you afterwards asking to meet up again. I don’t know about you, but I’d find that pretty flattering. Or, imagine a specific friend coming to you with an analogous situation, asking whether they should follow-up. What advice would you give to the friend? And, if it differs from your internal thoughts about your situation, why? Personally, I have yet to find a situation where the advice I give to the friend is worse than the advice I give myself.

A related and important skill is keeping in touch. Most people are really bad at keeping in touch, especially without a structure like university that keeps you in frequent contact. This means that many friendships fizzle without this structure. And this is really sad! I find a common mindset is ‘if friend X really valued this friendship, I wouldn’t be the one to always reach out’. But, empirically, I am confident many of my friends value our friendship, but also suck at reaching out. Being conscientious and organised is just hard

For me, much of the anxiety around following-up and keeping in touch centre on being a burden, and bothering other people. A mindset I find helpful is reframing it all as providing a public good. Taking social initiative is hard and most people aren’t very good at it. But most people do value fun social interactions. And, for some reason, people often enjoy interacting with me. This means that by taking social initiative, I am creating more opportunities for both of our lives to be better, which is something I find deeply motivating. ‘I want to be a person who creates win-win situations’ is fairly core to my identity. Whether it’s following-up, keeping in touch, organising parties, suggesting group activities, etc, I want there to be more people in the world who do this. So I want to cultivate this skill myself.

Relatedly, have good and clear communication about what we both want out of the friendship, and how the other person adds to our lifePeople often find this hard - it’s hard to eg communicate about ways the other person annoys you without harming them. For me, a key is creating clear and explicit common knowledge that we both value this friendship and are invested in it. This frames all clear communication as being on the same team - we’re trying to work together and share information, so we can both forge a better friendship

Exercise: Make a list of your good friends. Which of them do you feel closest to, and what has led to this? What blocks are there to being closer to some, and what are you going to do about it?