We have a loneliness problem as a society.

Cigna conducted a survey on 20,000 of their members.

• 54% said they always or sometimes feel that no one knows them well.
• 56% reported they sometimes or always felt like the people around them “are not necessarily with them.”
• 40% felt like “they lack companionship,” that their “relationships aren’t meaningful” and that they “are isolated from others.”

It’s probably no surprise to most people that it’s actually pretty hard to make friends, especially after college. It’s felt so universally that it’s become an extremely popular genre of meme.

As a thought experiment, what would you do if you moved to another city where you didn’t have an existing network? It’s a pretty daunting proposition without a ton of options (Work friends? Sports league? Meetups?).

We have online tools to connect and organize better, but it feels like they’re creating relationships that are more hollow and circles that are more insular.

Can we use them to make it easier to make friends?

To make good friends, the general consensus amongst sociologists seems to be that we need three key components:

• Proximity
• Repeated, unplanned interactions
• A setting that encourages people to let their guard down and confide in each other

Are there ways we can make it easier to satisfy those conditions to build more meaningful relationships?

How To Make Friends: Today

Friendship can broadly be broken down into three parts (as explained by this largely unnecessary graphic I made).

First we meet someone new. I actually think people aren’t terrible at meeting new people, there are lots of ways to do it (going to a Meetup, working with people, etc.).

The two main issues are that the meeting is still tied to your physical proximity and it’s hard to assess in one meeting whether someone has a personality and interest set that you vibe with. You’re essentially limited to the conversation you have in the first meeting (or a few more if you happen to run into them again) to assess whether or not someone is worth the potential investment of time to escalate the friendship.

It’s this escalation that I think most people struggle with. The investment required to actually turn a meeting into a genuine friendship is difficult, and requires at least one party to start proactively reaching out and making that happen. As a friend of mine said, it’s tough to go from “weekday” to “weekend” friends.

And finally there’s maintenance. People have their own methods of keeping up with their friends (texting, responding to some social media post, etc.) and some are better than others. But in a lot of cases maintenance is either limited to a small circle of friends or it’s basically an “everything that’s happened in your life since last time catch up” which ends up orbiting the same topics.

It also feels like people are willing to put less effort in actively catching up to someone because they feel sufficiently up to date with their life thanks to social media. Social media is not actually catching up or knowing how someone’s doing, it’s the cherry picked positive moments of their life. We need to carve out regular time and places to be vulnerable.

I’ve been experimenting with some ways to improve the three parts of relationship building and while also incorporating the three requirements for building strong relationships.

How To Make Friends 2.0

Here’s how I think about the new way of making friends, with a more detailed dive into each section below.

Meeting

Even though meeting people isn’t hard, meeting the RIGHT people is. You ideally want to meet people you already know have similar interests with you/you know are cool people.

This is the function Twitter and writing plays in my life. By constantly broadcasting my interests/personality on the internet, you have a pretty decent sense of whether or not you wanna kick it with me. If you’re into healthcare, memes, internet culture, and self-deprecating humor, it’s pretty likely we’ll be friends.

And that friendship actually builds up over time before actually meeting. Physical proximity becomes less necessary, relationships are built agnostic of geography. The repeat, unplanned interactionshappen in the public forum consistently over time. This means flowing into an actual friendship when you meet is actually way easier, you already have a rapport from years of interacting online.

By making my interests clear publicly, it’s easier to find and meet people with those mutual interests regardless of where they are physically. I probably meet 75% of new people nowadays via Twitter, and have several times met someone in a city I’m traveling to via Twitter. And even though I’ve only interacted with these people on Twitter, I immediately slid into an awesome conversation with them like we’d been friends for years.

Escalation

A scenario: you’ve met someone cool and they’re having a get together or pregame at their place. However you only know the person that invited you — how likely is it that you’ll go?

I’ve been dabbling more in STRUCTURED group events. These events make it easier to incorporate an additional person and they’re not awkward to join even if you only know one person.

Some examples:

Escape Rooms — I probably have done 10+ escape rooms now and a big experiences fan generally (I’ve written about them extensively). Escape rooms are great because you can bring together disparate groups of people without it being weird, the structure makes it easy to break the ice, and you already have some mutual interests when you hang out after (the organizer + the experience).

Hot Ones — Recently I recreated the YouTube show Hot Ones with a friend. Basically 12 friends were paired up, came up with well-research/deeply personal questions for the other, and then would ask each other those questions while eating increasingly spicier wings. People invited their friends, friends of friends, and more. After it was over, the whole audience knew a ton about the 12 participants, and it became easy to launch into conversations based off of their answers.

P2P Ted Talks — I’ve so far hosted two P2P Ted talks, each with about 7–8 prepared talks and 30–40 people. These are easy to drag a friend to, they’re virtually no cost, and the talks provide a ton of easy conversation material to launch into. Hopefully will be hosting these regularly.

AirBnB trips — About 3 times a year I’ll book a big AirBnB and then invite people I know from different walks of my life/levels of friendship. AirBnB trips are nice because they provide organic structure. Going on a hike, playing yard games, hitting the ski slopes, cooking, etc. These are all group tasks that have a specific activity/objective and make it easy and non-awkwardly get to know people better.

I hope to do more of these kinds of structured activity to make it easier to escalate friendships, because as people become regulars to them they have repeat interactions with the same group of people. Plus, in some cases (e.g. Hot Ones), they structure of the event can make it easier for people to let their guard down.

A final note about structured events is that they require upfront investment from the participants before they actually join (e.g. they have to create a deck for Ted Talks, come up with questions for Hot Ones, pay $$ for Airbnb/Escape rooms). By requiring the investment earlier, people are less likely to flake and more invested in the event itself.

Maintenance

Two things I’ve been messing around with in the relationship maintenance category: systematic spontaneity and safe online spaces.

Systematic spontaneity is basically setting up processes to make sure you’re catching up with someone, but without it seeming robotic or inorganic. One thing I do, for example, is called text roulette. A couple times a week when I’m waiting for something, I’ll basically just scroll very fast through my messages and arbitrarily stop and pick a random person on that page to hit up and ask if they wanna catch up/do a call sometime. Usually it ends up being someone I haven’t talked to in a couple of months.

Safe online spaces are key to getting friends to open up. This is usually a one-on-one space or small group space and totally private. One experiment I have going is with 7 other close friends that are spread across the world. Once a week, a different person in the group answers at least 5 questions from a question bank that are designed to get to deeper issues in their life. This results in a life examination about every 2 months to a small circle, which results in a better understanding of each person’s headspace and more regular check-ins where the group can provide support.

Both of these maintenance experiments are meant to create repeat, semi-planned interactions and more safe spaces while making proximity less of a necessity.

All Of The Above

The newsletter experiment I’ve been running for the last two years is really meant to address all of the above. I ask one question per week, answer that question, and then post my favorite 3 answers in the newsletter the following week. I respond to everyone that sends me a response either way. The questions range from life tips, to deep introspection, to debates on a specific topic. I always answer and try to demonstrate some vulnerability and have found that people tend to reciprocate that.

What’s been interesting is that this newsletter has been a great way to meet new people, escalate relationships that are new, AND learn more about close friends or old friends. There are some people on the newsletter that I’ve reconnected with after 15+ years! And even with people I regularly spend time with, this newsletter has become a carved out space to ask specific questions that might not come up in everyday conversation but help me get to know them better. It’s not a super organic thing to say “hey, so what’re you struggling with today?”

You can sign up for the newsletter here if you’re interested.

Coda + Miscellaneous Thoughts

There are still so many ways to create and build strong relationships, but part of the battle is convincing people that experimentation in friendships is worth the investment. I‘d love to know how you’ve made better relationships in your life and I’m always down to talk about this.

Some other random thoughts I had while writing this piece.

• There’s a big opportunity to help the archetype “organizers” of friend groups make events happen. Companies like JoyMode make it easier but planning is still really hard and thankless (despite the fact that supply side here is pretty dependent on those planners).
• I have a deep respect for people that actively talk to newcomers to a group at an event. They don’t have to do that, but I’m sure the people who feel out of place really appreciate it.
• What about 360 degree feedback reviews with your friends? I’ve learned a ton about myself through these at work, how can I find out how to be a better friend?
• No one has quite mastered the online-offline community yet. It’s usually one or the other — but making it easy to meet people either online or offline AND transition that seamlessly to the other has yet to be cracked. Gaming communities are arguably the closest.