Leveling Up the Skill of Friendship: Maintenance

Wishing to be friends is quick work, but friendship is a slow ripening fruit. — Aristotle


How many friends have you lost contact with for… no specific reason at all?

It seems to happen all the time, doesn’t it? We like to tell new friends, “let’s keep in touch,” but then we don’t. Our past is littered with abandoned friendships.

In a sense, this is expected. Friendships have a life cycle and most don’t last forever. If you’re continually making new, better friends, you should expect to have less time for your existing friendships. Those then wither and die. Or, more often, they enter permanent stasis, frozen in time until something stirs them up again.

But sometimes, friendships wither and die and enter permanent stasis simply because we haven’t put in the maintenance work.

“Maintenance.” Not a very sexy word. It brings to mind a whole part of the lexicon we’d prefer never to think about: “chores,” “cleaning,” “troubleshooting,” “calling a plumber because the kitchen sink is a disgusting mess,” and so on. Yet everyone recognizes that maintenance is necessary. It’s unsexy work, but it’s work that must be done — otherwise the kitchen sink becomes grimy and might break down and then you’ll definitely need to call an expensive plumber.

This analogy is imperfect because maintaining a friendship is much brighter and more fun than taking care of yucky plumbing. But it’s worth emphasizing that it’s not as effortless as we might like. You need to take care of your friendships, to nurture them, or they will most likely break down or become forgotten.

Here are my thoughts on how to do this. I don’t claim to be an authority — I’m just someone who’s figuring it out, and who does that through writing an essay like this one. I think and hope it will be useful to you, too.

Table of Contents

This is part 2.2 of my series on friendship. You can access the previous parts, on why friendship matters and how to make new friends, from this table of contents. You can also jump to any of the subsections:

Pierre-Auguste Renoir - Luncheon of the Boating Party - Google Art Project.jpg

More classic art (Luncheon of the Boating Party by Renoir) to represent friendship, in this case showcasing how wine, food, and cool hats are the key to keeping good lifelong friends

Recognizing that friendship is not effortless

When I was writing this, I had an open email window on my laptop. The window was mostly empty. There was a friend’s email address in the To field. Then there was the very beginning of an email, something like “Hey, how’s it going?” Nothing more.

This is a friend with whom, years ago, I used to communicate via long, old-fashioned emails. I hadn’t talked with him since 2018, and I’d been meaning to reestablish contact with the same mode of communication as before.

That email stayed both open and unwritten on my computer for about three months, until — coincidentally enough — that friend contacted me through some other means, making me slightly ashamed to have waited until then.

Why didn’t I write that email? Not because I didn’t know what to say. Not because I was afraid of his reaction, or because I didn’t care about that friend.

Simply because it was work.

Communication is not effortless. It’s not always a huge effort — sending a text message to a close friend is pretty easy — but it’s more effort than doing nothing. And communication is only part of a relationship. People need love, help, support, and time. You need to be ready to give those out to the people who are important to you. None of that is effortless.

From an essay called “Friendship is work, and that’s okay“:

Just like romantic partnerships and family relationships, friendships require a delicate balance of compromising, apologizing, spending quality time, and even calling out inconsiderate or upsetting behavior instead of bottling it up.

We often don’t realize that friendship demands effort, because it is usually very enjoyable. Which is great! That’s why we want friends to begin with. But the need for work can be obscured by that enjoyment, and then we don’t realize we haven’t done enough, and then our friendship suffers.

So the first part of my maintenance advice can be summarized thus: recognize that friendship is work.

Avoid the somehow widespread view that friendship happens magically.1yeah, I realize I’m the one who put a My Little Pony: Friendship is Magic image in the last post. It is magic, but only in the sense of spending hours drawing pentagrams and incanting complicated spells. Magic is work! That they’re governed by fate. It’s seductive to think lifelong friendships are created instantly through the mere act of meeting a kindred spirit. Just like it’s seductive to think that romantic love is all about finding your soulmate and spending the rest of your life in unending bliss…

… which everyone who has been in an actual romantic relationship knows is bullshit. Romantic love is hard. But somehow we haven’t internalized the same lesson about friendship.

Keeping a friend you’ve just made

Maintenance work starts as soon as friendship is born. But at first, it’s usually easy work.

This is because the conditions that provided the initial spark are still there. That friend you made at work will remain your friend as long as both of you keep your job. Friends you met when you became passionate about your theater classes will easily stay friends with you as long as you’re into theater.

Let’s point out that almost everything in the make new friends section from the last essay still applies. If you keep doing whatever made your acquaintance turn into a friend in the first place — being kind, being interesting, making the relationship easy for them — then the friendship is likely to endure.

At least, until the conditions change. If you can control it, and care a lot about the friendships you made in some context, try whatever you can to keep the conditions constant. But of course, there are a lot of life circumstances we can’t control, such as finishing school or quitting a job, losing interest in theater classes, or simply having friends leave for their own reasons. And even when we are in control, other considerations — a career, a romantic relationship, family, etc. — will force us to sacrifice the ideal environment to keep our friendships. What then?

Keeping in touch when conditions change

That’s where the real challenge of friendship maintenance occurs.

How do you keep your friends from high school or university or your first summer job or the hometown you’ve left years ago?

How do you keep friends that you met through someone who’s no longer in your life — for instance, the friends of an ex?

One answer is that sometimes, your friendship was tied to that bygone context to such an extent that it will never be the same again, and you shouldn’t try. But that certainly isn’t always true.

If you’re intent on staying friends even after circumstances are bringing you apart, you’ll need to put in some more maintenance work. The first step is to initiate contact frequently. People are bad at reaching out. People vaguely think about contacting you, and then they keep a draft message open for three months and never send it. You can’t fix that for them, but you can fix it for yourself and maintain your friendships that way.

One trap you want to avoid is to assume that if a friend hasn’t contacted you already, it means that they don’t want to see you. It’s really easy to think that, especially if you’re shy or socially anxious!2Source: am a shy and socially anxious person, or at least I used to be. But it’s also easy to convince yourself that it’s almost never true — just realize that your friend might be making the exact same assumption, since you also haven’t contacted them for exactly as long.

Of course, it’s sometimes the case that someone you consider a friend doesn’t want to see you anymore. You need to read the room. If you’re always the one initiating contact and your friend doesn’t seem that keen to see you, you might want to stop trying. We’ll consider this in more detail in the essay on ending friendship. But I want to say this: a long time with no contact is not by itself evidence of unrequited friendship.

Concretely, what does maintaining a friendship look like?

It can be as simple as a “maintenance text” — just sending a short message every once in a while. My friend Rishi writes, in How I keep in touch with friends after college:

It can be a:

  • Dank meme
  • Interesting article
  • Piece of sports news
  • Shared memory
  • etc.

Receiving any of those things means the other person was thinking of you, which is just the sweetest thing.

It can go further, of course. Invite your friend over. Grab some food or play a game. Suggest a phone call or video chat. If they live far away and you can afford it,3and there’s none of this horrible covid-19 thing restricting travel travel to visit them! As a bonus, they’ll even be able to show you around, which is the best way to do tourism.

Some occasions are particularly suitable for maintenance texts/calls/etc. Birthdays, for instance: you have the perfect excuse to send something to a friend — so why not add to your birthday wishes something like “We should have a call, it’s been a while!” Your own birthday is also a good time to suggest hanging out to whoever is sending you wishes. Other holidays, e.g. New Year’s Day, are similarly convenient.

Those calendar events are Schelling points — easy dates to coordinate around by default. But you can also create your own recurring events with a friend. For example, decide that you both go watch a movie at the beginning of each month. In other words, create a habit — which is one of the best ways to make work not feel like work.


Not everyone is that bad at reaching out, and so you will also be on the receiving end for many of your friendships. My suggestion, if you care about those friends, is to make a habit of replying quickly when they contact you. In fact, make a habit of saying yes to whatever they’re inviting you to — or, if you must say no, immediately reschedule or suggest another activity.

There’s a real danger, when you decline invitations too often, of letting your friends think you don’t want to see them. It helps to directly tell them that it’s not the case. Say “Sorry, I’m really too busy this week, but I’m really happy you invited me! How about we grab lunch together next week?”

(I have a friend who told me something like that, and it truly warmed my heart. But it’s been a couple of months now. Hopefully that wasn’t a strategy to tactfully get rid of me.)

If on the other hand you don’t care about those friends, well, perhaps friends isn’t quite the right word then. This is a matter for when I’ll write about the end of friendship.

You may also find yourself on the side of doing the work alone, with no reciprocity. This is not an ideal situation. As I mentioned earlier, that may just mean the friend isn’t very skilled at friendship, but it could mean they’re the ones who don’t care that much about your relationship. As a friend told me, “even a ‘well-maintained’ friendship can crumble if the maintenance work isn’t shared.” I don’t think the work should necessarily be shared equally, but it can’t all fall on the shoulders of a single person. That’s too much to bear.


If you have a lot of friends and acquaintances, that’s… a lot of data to keep track of, actually. There’s basic stuff like birthdays and email addresses, but also who likes what kind of food, who has feelings for whom, who enjoys what sort of event… Humans do come equipped with a lot of mental power to process social data — for around 150 friends, to bring up Dunbar’s number again — but there’s no shame in getting a bit of technological help.

For many, social media data is largely sufficient. Facebook will remind you of birthdays and provide a convenient way to contact people. But not everyone is on whatever social media you’re using (probably for good reason), so you might still want to take extra notes. It can be as simple as keeping track of email and physical addresses in a notebook or text file.

But you can get fancier. Nat Eliason has a detailed blog post on what he calls his personal CRM (contact relationship management) system. He keeps track of:

  • First & last name, email
  • Industry / skills, Company
  • Interests
  • Location
  • How we met

I don’t think that this particular solution fits everyone, but I’ve started doing something low-key similar, and so far I like it. Sometimes there are little details about people that you’re not going to remember by yourself. For instance, I have a friend whose taste buds will not tolerate cilantro. If I invite her over for dinner, and look at my few notes about her, I will not cook food with lots of cilantro (I love cilantro). Everyone wins!

Is it weird, though, to take detailed notes on people? It somehow feels like it goes against some social norms — yet I can’t really see why. You keep information and impressions of people in your head all the time; it’s not very different to keep them in written form, as long as they remain private. Still, I rarely write anything personal in my own notes, perhaps because it’d feel like a transgression. I suppose the answer here depends on your own level of comfort.

Scaling it up

Everything I’ve told you so far is useful,4at least I hope so but it all assumes we’re talking about 1-on-1 relationships. If you have a fair number of friendships you want to maintain, it’ll be a lot of work, both for you and each of your friends. Fortunately, there are ways to become more efficient.5“Efficient” might sound too productivity-centered for something as sacred and beautiful as human relationships, but even if you don’t think of it in those terms, you still need to be efficient! You have limited energy to do the work of maintenance and it’s good to be wise about how you spend it.

Am I just going to tell you to see several friends at once? Yeah. Organizing a group event requires more work than a 1-on-1 — scheduling is more complicated, and maybe you need to get your house in order if you’re hosting — but it’s often worth it. It’s rewarding, it makes people happy to be invited, and you see many of them at once in a fun context.

But if you’re going to organize a hangout with many friends, why not make it recurring? I already mentioned that creating habits is a good way to foster a 1-on-1 friendship; that’s even more true for group events. Make them low-key, with flexible guest lists, so that they happen regardless of any specific friend’s availability — and suddenly you have created a Schelling point for a whole group of people.

Weekly dinners are perhaps the most common example. I lived in the Boston area for a little while, and the Friday evenings at some friends’ group house were a highlight of my time there. There was something really warm with the idea of joining this ever-changing group of people6there was, however, a core of regulars, which I suspect is a prerequisite for the event to persist over time for fun discussions and food every week.

It doesn’t have to be weekly, though — monthly or even yearly recurring events can work great. It can also go beyond dinner parties, like outdoor activities or game nights, as long as the events don’t get too complicated or costly.

The whole idea is to make it easy for your friends to join. To perform the maintenance work for them. This reduces the total amount of work needed, and isn’t much harder than organizing 1-on-1 hangouts.

Self-sustaining friendship

There is a final trick I need to tell you about, and it is the best trick of all. With this strategy, you can make the work of friendship maintenance perform itself with minimal effort, most of the time. The trick is to create a virtuous cycle, in which friendship begets friendship.

Friend groups are the logical next step to recurring group events. When you have a cohesive set of people who see each other regularly, eventually the group seems to get an identity of its own. It becomes a tribe; you get a feeling of belonging. But more importantly, the group’s continued existence depends on very little individual maintenance work; everyone can contribute, to the advantage of everyone else.

Rishi writes:

If you’re like me, you can’t be trusted to maintain a friendship 1:1 by calling and texting all the time. You get busy. In a friend group situation, your amazing friends keep each other engaged. This way, you’re relying on a system instead of willpower.

You still need to contribute some; if no one does the maintenance work, the group will disintegrate. In fact it’s likely that the distribution of work is unequal — we all know of situations where one friend is responsible for holding the group together. Which isn’t necessarily problematic, except insofar as it makes the group fragile.

But in an ideal group, any effort you put in will be amplified by your other friends, and their actions will be in turn amplified by you. Thus the system becomes self-sustaining.

Concretely, the easiest way to get this is to join an existing friend group, though you can also create your own. The means are diverse: recurring events, co-living, common projects, or simply online chat groups.

There is another, more personal type of self-sustaining friendship: deep friendship.

When you get very close to someone, it doesn’t really matter whether you send a text message every once in a while. You can in fact spend years without any contact. “No matter how long you spend apart, when you come back with your friend, it is like no time has passed at all,” as C.S. Lewis wrote.

The ordinary maintenance work becomes unnecessary, or so easy to do that it goes unnoticed — although perhaps that is an illusion. We’re less at risk of losing a close friend due to neglect, but when help must be given, for instance in times of crisis, the demands will be greater. Maintenance work is still needed, but its nature has changed.

Still, deep friendship is rewarding and less taxing in our daily lives. It’s a whole other topic, however. We’ll cover it in the next post.


Thanks to Gregory Yang Kam Wing, Taylor Pullinger, and the wonderful people in Writing Workshop Juliet for feedback on this piece.