Introduction

One of the greatest sources of joy in my life are my close friends. People who bring excitement and novelty into my life. Who expose me to new experiences, and ways of seeing the world. Who help me learn, point out my blind spots, and correct me when I am wrong. Who I can lean on when I need support, and who lean on me in turn. Friends who help me grow more into the kind of person I want to be.

I am especially grateful for this, because up until about 4 years ago, I didn’t have any close friends in my life. I had friends, but struggled to form real emotional connections. Moreover, it didn’t even occur to me that I could try to do this. It wasn’t that I knew how to form close friends but was too anxious to try, rather, ‘try to form close friendships’ was a non-standard action, something that never even crossed my mind. And one of my most life-changing experiments was realising that this was something I wanted, and actually trying to intentionally form close friends. 

It’s easy to slip into a passive mindset here, to think of emotional connections as ‘something that take time’ or ‘need to happen naturally’. That to be intentional about things is ‘inauthentic’. I think this mindset is absolutely crazy. My close friendships are one of the most important components of my life happiness. Leaving it up to chance feels like passing up an incredible opportunity. As with all important things in life, this can be optimised – further, if done right, this adds a massive amount to the lives of me and of my future close friends.

The first half of this post is the story of how I approached intentionally forming close friends, and the second half is an attempt to distill the lessons I learned from this. As such, this post is more autobiographical than most. Feel free to skip to the advice section if you don’t want that. Further, what you value in close friendships is highly personal – this post will focus on what I want in friendships and how I try to get it, but you should adapt this to your own situation, values, and what feels missing in your life!

Exercise: Think about your closest friends, and how these friendships happened. What needs are you fulfilling in each other’s lives? Are you happy with this state of affairs, or is something missing? What could be better?

My story

The Problem

Back when I was in school, I never had close friends. I had friends, people I liked, people I spent time with, whose company I genuinely enjoyed. But I was pretty terrible at being vulnerable and forming emotional connections. These friendships rarely went beyond the surface level. In hindsight, I expect these could have been far richer (and I’ve formed much stronger friendships with some of these friends since!), but I never really tried.

I find it hard to introspect on exactly what the internal experience of past Neel was like, but I think the core was that trying wasn’t available as a possible action. That I spent much of my life doing what felt socially conventional, normal and expected, for the role I saw myself in. And ‘go out of your way to form emotional connections’ wasn’t part of that. It wasn’t an action I considered, weighed up the costs and benefits, and decided against – it never even occurred to me to try. It didn’t feel like a void missing from my life – things just felt normal. It was like playing a video game, and having a list of actions to choose from, like ‘ask about their day’, ‘complain about a shared experience’ or ‘discuss something cool I learned recently’; but this list contained nothing about ‘intentionally form an emotional connection’. It wasn’t in my reference class of things I could do.

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.

The solution

Despite all this talk of agency, I stumbled my way out of this problem pretty much by accident. When I was 18, in my final year in school, I ended up in a long-term romantic relationship (with a girl who, thankfully, was far better at taking initiative than me!). And this was one of my first times really feeling a deep, emotional connection with someone. And, surprisingly, found that this was great, and added a ton to my life! And further, got a bunch of surface area on what emotional connections actually felt like, and how they formed.

That relationship ended in my first year of university. And as part of trying to move on and recover, I did a lot of introspection on how the relationship had changed me, and what now felt missing from my life. And one of the biggest things missing was having a deep emotional connection with someone. So I decided to fix this.

The obvious next question was, what to actually do? In full 19-year-old-Neel fashion, I took a pretty reductionist approach to this. I made a list of all the people I considered close or close-ish friends, and tried to figure out how we became close friends. And in each case, I identified the main shifts in our relationship after intense, 1-1 conversations, where we were both being emotionally vulnerable and authentic, and talking about personal things. So, to make more close friends, all I needed to do was engineer more of these 1-1 conversations!

This was also inspired by a time when I was 17, and at a rationality camp for high-schoolers. We were doing a workshop on Comfort Zone Expansion (CoZE), where the intention was to identify something we were uncomfortable with but wanted to explore and try in a safe environment. I and another participant noticed we were both uncomfortable with being vulnerable and authentic, and tended to use humour to deflect from anything personal. So, we decided to find a private place and spend two hours having a fully authentic conversation, with no deflection allowed. This was kinda terrifying, but also a really great comfort zone expansion experience, and I felt much closer to him afterwards.

One decent way of engineering an authentic 1-1 conversation is to go through a bunch of personal and vulnerability-inducing questions together, a la 36 Questions that Lead in Love (after cutting the ⅔ of questions that I found dull). So I made a list of questions I considered interesting, which I expected to lead to authentic and vulnerable conversations. And then went up to the 10-20 people I felt most friendly with, explained the experiment, and asked if they’d be interested in blocking out a few hours, and going through the list together. 

Somehow, this worked! About 80% of the people I asked said yes, and I felt much closer with about 50% of them afterwards. Some people were weirded out, but most of my friends were down to try the experiment. With some people the questions felt awkward, but with some people I really vibed. And some people were extremely enthusiastic about the idea from the start – I explained the idea to a guy I vaguely knew, he loved the idea and suggested doing it together, we hit it off immediately, and he’s now probably my closest friend. 

If you’re interested in the questions, you can see the full list here. Some of my favourites:

• 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?

Retrospective

I am incredibly happy I ran this experiment. It has made my life massively better. And, in hindsight, I am still really surprised that the success rate was so high! If this idea sounds compelling, I would highly recommend people try it – it was an excellent growth experience.

That said, I still somewhat cringe looking back on that. I think having a literal list of questions made the interactions much more artificial. Since then, my conversational style has evolved to be a lot more natural, while trying to preserve the spirit. I really like asking questions, and will often weave these questions into a conversation if appropriate. And strongly try to create an atmosphere where people are comfort