How to transform your social life

plus the pros/cons of having a lot of friends

I’ve experienced two versions of social life in New York:

1. You know a handful of people in the city but you don’t ask them to hang out because it makes you anxious, no one invites you to things, and you spend most weekends entirely alone. On Friday nights you feel depressed that the workweek is ending and you have no plans, so you send an office-wide Slack message asking if anyone wants to get dinner, which of course no one responds to because they all have lives.

2. You are invited to multiple parties every weekend (housewarmings, housecoolings, birthdays, salons, picnics, launch parties), you frequently ask people to hang out without a second thought, you host things every month, you meet several new people each week, and you make connections with random people on the internet who are interested in getting to know you.

It would have surprised me a few years ago to discover that it’s possible to go from (1) to (2), but indeed it happened for me, in the span of about a year. Here are the things that helped me make the transition.

Make it a game to initiate as much as possible, even when it makes you anxious.

I can’t stress how surprisingly effective this technique was. For the first year or so that I was in New York, I was in this weird place where I knew a few other people in the city, but I didn’t really feel close to them, so I was hesitant to ask them to hang out. And then I got sick of my hesitation and wrote this:

link

And I kept this literal log of every single time I messaged someone and felt uncomfortable about it:

With enough practice and loving awareness at each instance of discomfort, this eventually became easy, and I stopped having to make a note of the discomfort at all. (Concretely, between November and December 2021, I wrote down approximately 50 such moments. After two months I no longer felt the need to do this.)

The same practice can be helpful for any uncomfortable activity that you repeatedly have to do. I think making the written note is crucial because it helps to create a vivid juxtaposition in your mind between (1) how uncomfortable you felt at the moment you did the activity, and (2) how totally unimportant it feels when you’re looking back at the note a week later. This juxtaposition helps train your brain to be less afraid of the activity, perhaps.

I’ve used this same approach for various other things that I wanted to conquer my fears on, e.g. “going to parties where I don’t know anyone and I feel nervous” (currently at 13), and “feeling cringe when posting on social media” (currently at about 50), among others.

Start a blog and/or twitter and/or other social media thing.

There are a lot of things that suck about social media, but one of the best things is that you get to connect with people who have the same interests as you.

“But what do I say/post?” Whatever you’re already saying/doing in your life, but you just put an artifact of it online. If you like making art you can post art. If you like reading science textbooks you can talk about your learnings from science textbooks. Twitter is a fairly easy to get rolling with because you can just post whatever random thoughts pop into your head, and unless you’re enlightened I’m sure you have plenty of those.

You don’t need a big following to make friends off the internet. On twitter I started connecting with people when I had less than a hundred followers. Anytime you see someone whose stuff you like, you can DM them and say “hey I really like your stuff!” And maybe follow up with “would you be open to a social call sometime?” (More opportunities to expose yourself to rejection!)

One caveat here is that social media is easy to get sucked into. You can use various tools like blockers to make sure you’re not overdoing it on the consumption side.

Host things.

What kinds of spaces, events, gatherings do you wish existed more? Hosting is a great opportunity to craft your social life into exactly what you want it to be, because you can set the intention and the tone and the participants of the gathering. Maybe you wish there was a knitting club. Why not start one? It can just be you and two of your friends.

If you do this consistently, very interesting things can happen. You’ll get introduced to people who want to host your gatherings in their spaces. You’ll meet other people who are into hosting and discover the enormous breadth of social spaces that exist in your city. You’ll also just make a lot of new friends by virtue of your friends inviting their friends.

When you host something, be sure to talk about it (on social media), so that people are aware you’re doing it. Even if they don’t join the first time, they will be more interested in joining later. This will also make it more likely that, for example, someone offers up their apartment or community space for you to host in.

Notice when you are identifying yourself as “a desperate loser”, and try not to reflexively flinch from this.

One of the difficult things about trying hard to make friends is that it can make you feel bad. The first thing to keep in mind is that usually people aren’t thinking about you and if they say no to you, they’re probably just busy and it’s not personal. But sometimes people will judge you, or they’ll think you’re a “loser”. This is actually okay. Practice saying this out loud: “maybe I’m a loser by someone else’s standard, and that’s okay.”

This will make all of the previous tips easier to execute on, and it will make other things in your life easier too. In the words of Sasha Chapin, “a lot of happiness comes down to your willingness to cross the moat of low status between you and doing things you want to do.”

Something something soft skills.

I’ve tried to orient this guide towards specific, mechanical strategies that increase your opportunities to come into contact with other humans. But there is a whole other set of skills that are helpful once you’re actually face-to-face with them.

Other people have written at length about these skills, but the simplest advice I can give is: be honest and be interested. Often what gets in the way of our connection with others is this feeling that we have to try to contort ourselves into a shape that we don’t naturally take. But this will just make you look more uncomfortable and tense, which doesn’t help. Instead you can just be honest and trust that even if you don’t meet the people who will become your people tonight, you will eventually meet them and it will feel great.

Some of us (perhaps most of us?) just get awkward and nervous at parties, and this is fine. You don’t need to fight the nervousness. Most people will understand and feel the exact same way, and they will like you anyway, for reasons that cut deeper into the essence of who you are.

The complement to being honest is to be interested. Give the other person your full attention and see what you might have to learn from them. Ask them lots of questions. An influencer from the 1900’s once said: “You can make more friends in two months by being interested in others than you can in two years by trying to get others interested in you.” (Keep in mind that it’s possible to overdo this, but I don’t think most people are at risk of having this problem.)

Other approaches

• Start/join a club or class

• Go to a cafe regularly and strike up conversations with strangers (talking to strangers is something I’m still pretty awkward with, but this seems to work for people)

There are factors outside of your control

It’s important to acknowledge that the transformation I experienced wasn’t purely due to me deciding to change my life: there were various other things that helped, like some old friends moving into the city, and moving in with new roommates in an apartment with a slightly bigger common area (by NYC standards). I know people who have a harder time making new friends, as well as people who’ve had it much easier and had a full social life almost immediately after moving here. The point is that you shouldn’t take your starting point as a reflection of your character. You also need not be discouraged if it’s taken you a while to work up the courage to try to make new friends. With enough persistence your social life is bound to become richer and more fulfilling.

What happens once you have a lot of friends?

People often think “oh my god that sounds so nice.” And first of all, okay yes it feels good to have a lot of friends. It’s more likely that one of your friends will be free to hang out on any given Friday night, and it feels good to not have to be the one initiating always. At the beginning I was initiating almost every one of my social encounters, but over time the amount of active organizational effort I had to put in to have a social life decreased, and in some stretches it has been literally zero.

Here are some of the downsides because people don’t talk about that as much. Having a large social network can create more noise in your life, and can serve as a distraction from work you care about doing. Also, if you’re not careful, it might hinder your ability to build depth in your friendships. If you just have five friends you’re close with and excited to spend time with, it’s really easy to keep building a deeper friendship with those people. If you have fifty people you’d like to spend time with, and all of them are busy to varying and unpredictable degrees, you are more likely to keep bouncing back and forth between different social groups and friends based on availability and convenience. It’s difficult to regularly keep up with more than a handful of people, and having to be in a position to “choose” who to spend more time with and who to spend less time with kind of sucks. Also, some people will be upset with you because you are less available and don’t respond to their texts as quickly, and if you’re not comfortable with setting boundaries this will be very unpleasant.

One other strange consequence to making a lot of new friends is that you can start to become attached to the idea of being “a popular person”, which then makes certain situations feel more threatening. For a while I had grown used to hosting things where I knew almost everyone, which then made it comparatively harder to attend parties where I knew almost nobody. That’s a different kind of nervousness I’m now trying to work on. Also, while the general negative valence of social rejection decreases substantially in intensity, you’ll still have the occasional situation where you really vibe with someone and want to be friends with them but they’re too busy and you feel sad. The point is: you won’t be completely free of insecurities and self-doubt; some things will become easier, some will become harder. The real victory is to be able to enjoy your newfound friendships, while being able to fluidly oscillate between seeing yourself as “person who is a loner and that no one wants to hang out with” and “popular person that people really like”, while noticing the totally contingent and ephemeral nature of both of those views.