The Fine Art of Keeping Friends

The Modern Survival Guide #68

Pictured: Something that gets increasingly hard as you get older — getting more than three people together at once.

This is the Modern Survival Guide, a guidebook I’m writing for things I think people need to know about living in the modern world. The views expressed here are mine, and mine alone. It’s not a lot of fun being alone, though, and I deeply value my friends. The trouble is, the older I get, the harder is it is to keep them. There’s an art form to maintaining long-term friendships, and that’s our topic in this article.

So let’s get one thing straight off the bat — for most of our lives, the majority of our friends are going to be people we see as part of our normal routine. Most of my friends fall into the category of Work Friends, for example, if only because the people I see most in my life are the people I work with.¹ Similarly, a lot of my friends are people I see at my regular activities, people I’ve met through sports or playing board games at my local game shop.

This article isn’t really about any of those people. Those friendships will take care of themselves, right up until the point where they won’t, and that’s what we’re here to talk about today. Because once someone moves out of our immediate orbit, we start having to put real, serious, no-kidding effort into the relationship. As your activity level decreases and your social live slows, the number of friendships you don’t have to work for will dwindle. All of which is to say that once you’re out of your 20s, you’ll have to put out some effort to keep a lot of your friends.

Maintaining these friendships is still vitally important, though; some of the best relationships in my life are with people who I only see a few times a year, but we just click as soon as we’re back in the same room. These are the people who get invited to my major life events, who I trust to give me advice, who I can call upon for help, and who form my long-term social network. These are the people who become family.

But make no mistake, it takes work to keep that kind of relationship going, and it’s more art than science. There are very few hard-and-fast rules for trying to keep friends as you age, so instead I’m going to go with five main suggestions:

  • Maintain contact (even minimal contact)
  • Set up recurring meetings
  • Have traditions
  • Show up for life events
  • Travel (if you can)

I’m not saying these are things you have to do, I’m just offering some ideas that seem to help in my life. Take or leave them as you will.


Keep in touch. This seems like the simplest thing in the age of high technology and social media, but it’s the difference between feeling like you’re able to reach out to someone and being afraid to pick up the phone. Seriously — how many friendships have you had slip aside simply because it wasn’t convenient to talk to someone for a while, and then you didn’t know what to say, and then it just felt awkward to reach out? I think for most people, the answer would be a significant number.

So stay in touch. This can be as simple as liking and commenting on a person’s posts on Facebook, or sharing an Istagram photo, or just sending a text every once in a while. This is the first, hardest step in maintaining a long-term friendship.² Once you have contact, though, a lot of other options fall into place.

Recurring Meetings

It’s an interesting psychological tendency of human beings to treat things as more “real” if they’re on a calendar. Strange but true for the majority of people, if you put an event down on paper it’s more likely to happen. So it follows that if you want to keep in touch with someone, having a recurring meeting date (like the 2nd Saturday of every month, or something similar) is a very good way to make time to see them.

And this meeting could be pretty much anything. It’s worth noting that there’s some evidence that men and women process friendships differently, for example, with men’s friendships being more activity-based and women’s being more conversation-based.³ So a “recurring meeting” could be anything from a coffee break to an annual trip to Thailand. The point is that you share physical proximity with your friend on a regular, expected basis. I know, I know, we live in an age of telecommunications, but there’s still no real substitute for seeing someone face to face.


The concept of “tradition” is something of an anachronism in the modern cutting-edge disruptive worldview, but it is super important for maintaining long-term friendships. Traditions serve the same general purpose as recurring meetings, but with a dash of ritual thrown in that makes the experience “yours” in some meaningful way. This is basically one step up from just having a recurring meeting; sometimes these meetings turn into traditions.

For example, for many years my family had a tradition of going camping in the summers. We’d load up with some family friends in a couple of campers and go trundling off to a local lake, where we would fish, rent a boat, water ski, have campfires — you know, lake stuff. It didn’t occur to me at the time, but this is a key reason why my family still has those family friends; we all had years of bonding experiences that were expected, normalized, and planned for months in advance.

Tradition serves a lot of purposes in human society, and most of them boil down to “glue.” A good tradition can hold together a group of friends, and serve as a highlight of the year, even when people live far apart from each other.

Show Up for the Big Games

A lot of the time, you’ll know the difference between an acquaintance and a friend based on who shows up to the big events. Simple as that. The people who show up for your marriage, for your kid’s first birthday, for your dog’s quinceanera, or for whatever you judge your life’s important events to be — those are your friends.

So, on the flip side, if you want to put in the spadework to stay friends with someone, it is important to show up to their stuff. Yes, I know, we’re all adults and we’re all tired, and Jesus Christ most of us have kids and who has the time and holy shit Game of Thrones is on! Yeah. It’s gonna be hard. That’s the point. Showing up for other people’s events is a sacrifice. You sacrifice your time and often your money to make sure the other person knows that you value them, and with luck that sacrifice is honored.

Travel (If Possible)

Last but by no means least, when you can, if you can, travel to reconnect with far-away friends. If it holds true that your friends are the people who celebrate your life events with you, this goes double for people who will drive a few hundred miles just to hang out!

Traveling for a friendship is often something of a grand gesture. Through this action you are saying that you value the relationship enough to expend a significant amount of money and time on it. And by hosting you, your friend is saying that they value the friendship enough to relinquish their privacy and perform host duties on your behalf.

Most people on Earth have no real ability to travel often for the sake of friendship, so unless you’re buds with a millionaire, this is the kind of thing that should seriously signal that you want a friendship to remain alive. If the other person reciprocates, this is a great way to maintain that friendship.

Letting Friendships Fall

To wrap up, I’m going to say something that is sad but true: we should actively choose to let some friendships fall by the wayside. As the old saying goes, some people are with you for a reason, some for a season, and some for life. Not everyone you meet is going to be your friend, and not every friendship is going to last forever, and that’s ok.

The point of this article isn’t to help you keep every friend you ever make. The point is to keep the friends you want to keep. And the subtle issue, of course, is that these friends also have to want to stay friends with you. Nothing in this article should be taken as a positive guarantee that someone will want to stay friends.

So — some of your friendships are going to fail. You have a role in this, and it is to make deliberate choices as to who you want to keep in your circle and who you don’t want to maintain a relationship with. In general, there is a set of rules here, and they are:

  • If someone is toxic, drop ’em.⁴
  • If you just don’t get along, drop ‘em.
  • If it takes lots of energy or stress to be around someone, drop ’em.
  • If they don’t want to be around you, drop ’em.

And by “drop ‘em,” I don’t mean send them a mean note and burn a bridge. There’s no need for that, and no point to it most of the time.⁵ All you have to do, in most cases, is simply cease contact. It’s not ghosting, it’s just moving on.

But for the friendships you want to maintain, my best advice is just to keep reaching out, if nothing else. The ideas listed here can help with that, but ultimately it’s all about just reaching out. We’re all islands. That doesn’t mean we can’t build bridges. Reach out and see who takes your hand. Those people will be your long-term friends.

¹Incidentally, this is why you should get a new job if you don’t like the people at your current one — you’re going to see them more than anyone else in your life. Make sure that interaction isn’t toxic.

²I have a friend who shall remain unnamed (you know who you are!) who is just bad at this. He will go weeks, sometimes months, before responding to people’s emails and text messages. It’s not because he doesn’t like us, it’s just… he doesn’t get it. Drives me nuts, and it has driven away some of his friends. Look, if you’re an adult and you’re living in this century, you can take thirty seconds to reply to a text message. You just can.

³Although this is murky science and shouldn’t be taken at face value. Whatever activity or action feels most appropriate for a particular relationship is probably most appropriate for that relationship, and tell the shrinks to take a hike.

⁴Toxic friend: someone who brings you down rather than up, who takes much more than they give, who demands support without offering it in kind, who is as self-centered as a gyroscope, or who can’t be trusted with your information. Drop these people like third period French. It’s not your job to make them good humans unless you’re a priest, psychiatrist, or social worker.

⁵I.e., unless you want to send a message because someone has wronged you, it’s not really worth it to bother with formally telling them you don’t like them.

Searching for truth in a world focused on belief.

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