Skip to content

How I maintain friendships: A toolkit

Westley Dang
Westley Dang
7 min read
How I maintain friendships: A toolkit
Photo by Noorulabdeen Ahmad / Unsplash

Maintaining friendships is hard. It's even harder for friends in different time zones, friends who are busy and/or ambitious, and friends who have just fallen out of the radar over the years. I am reflecting on a few useful tactics I've accumulated over the years.

I hesitate to publish this because I'm afraid of it'll be interpreted as instrumental. I came up with the names an hour ago, only to help the reader remember.

Don't just employ these tactics as means to an end; I invite you to aim to be the kind of person who naturally finds creative ways to connect. Embody the friend you want to be, don't just act it out. In the end, it's not the number of interactions that deepens friendships, it's who you are during them.

The "Value-add"

This isn't a "play," per se, but it's important because once you read this, you'll know why the other plays make sense: I have learned to STOP asking "how are you?" It's a lot of burden on the other person. Where do they even start?

Instead, I try to "add value first." I offer a funny or heartwarming story from my life, or a photo of something they'd relate to. I usually inquire about something related to the last time we talked (what they've been struggling with, what they're been excited about, etc.). Good friends remember the details. In other words, don't ask the other person to start the fire; be a good guest, and come with the kindling already lit.

This isn't to say checking in with a "how are you" is completely useless. It can be posed and answered meaningfully, with the right relationships. But for most people, there are worthier alternatives like, "what's been on your mind lately" and "how are you feeling about life in general" and "what are you looking forward to?"

The "Pop-in"

If I'm going to be in some neighborhood that I don't live in, I'll text some of my friends who live in the area to let them know I'm nearby and I'd love to "pop in" if they're free. It's one step removed from just showing up at their door (a lot of cultures still do this!), but texting first gives my friend permission to veto if it doesn't work for them.

Last week, I was at a work-related networking event and texted my friends who live a few blocks away. It turns out they just had just delivered a baby four days prior, so not only did I get an early look, but also catching up with my friends in that post-natal period is precious in itself.

The "Pop-up"

I don't want to have to plan a whole thing just to chill with my friends, and I don't want the burden of hosting either. I have a whole anxiety around whether people will show up. So to make it more chill I'll post up somewhere with a book (a park or a coffee shop) and then let some of my friends know that I'm going to be there if they would like to join. Statistically, it leads to a small group or just one person, but as an introvert, this is the perfect size to not drain my social battery (did someone say Poisson distribution? 🤓).

I appreciate when friends do this with me. Example: my friend texted me saying she's at a Casements (a bar) and live music spontaneously appeared. I was biking home from work and was about to for my evening run, but chose to join her instead. Then my brother joined because he got locked out of the house. He helped me finish my second beer. Then we ate Mission tacos down the street, where I had a salsa so spicy I was crying for 15 minutes. I also then discovered how fluent my friend is in Spanish.

(I did not run after)

The "Flashback"

Text someone immediately when something reminds you of them. One of my best friends from grad school and I used to "sneak out" to get late night fast food, as if we were haphazardly having an affair (we were strictly platonic). We'd indulge in the secrecy, and eat in the car lest anybody finds us. It was usually on Fridays when McDonalds would have $2 Filet-o-Fish, but we'd also do this for the debut of new chicken sandwiches. Sometimes we'd let another person join in on our tryst. Now, she's 500 miles away and has a family, and neither of us eat fast food, but on the rare occasion I do, I'd text her immediately and tell her we need to sneak out again soon.

It's also just nice letting my friends know I'm thinking of them, and always try to make it interesting how I'm thinking of them.

The "Soft Now"

I have a friend who I will text to catch up, and then she'll offer that she's free for a call for the next few hours. She, in particular, is good at what I call the "soft now" – it's like now, but not now-now. To me, the gesture says, "I can prioritize you, if you can prioritize me." This has been really effective for squeezing in some quality time with a friend through a phone call. It also comes with the understanding that it's a late notice, and it might be ok for you to be doing something else (I was folding my laundry last time we called). The "Soft Now" is more casual and less formal, which is how I tend to like my friendships.

The "Hard Now"

I don't do this, but some of my friends will FaceTime me with no warning, which is weird for me because "hard now" phone calls are for ambulance-level emergencies, but I respect them for trying to change the culture around phone calls. By the end, I always appreciate receiving the "hard now" calls. It feels more intimate than a planned call. They delivered something I didn't know I needed!

The "Favor"

Ask your friends for favors instead of spending money on services. One time I rented a car that I muddied up because I took it backpacking, and I needed to get it cleaned before returning it. I could have spent $15 to run it through a car wash, but instead I called up a friend to ask if I could use her garden hose for a spray down. I spent more time driving to her house than it would have taken to go through a car wash, but it was time well spent because we were able to catch up.

Asking friends for favors is how you deepen relationships: It's the give-and-take dynamic, the vulnerability of asking for a favor, the affirmation from your friend who is willing to help, which strengthens the feeling of knowing you can rely on each other. A lot of our economy is built on being able to offer services to those who want to be independent, because that's just the American way, but inter-dependence is the key to stronger relationships!

The "Podcast"

Send really long voice messages to each other. I have a dear friend who is busy with her two kids, and sometimes it's hard to even find time to get on a phone call without being interrupted (ugh, children are so needy!). She appreciates getting the 5-10 minute voice messages from me through WhatsApp because she can listen while she's doing the dishes or on a driving commute. This is also an interesting format because it's actually difficult to monologue for that long... but it does make me delve into the topics a little deeper as I'm recording. It almost feels like journaling.

The "Half-Birthday"

Find any excuse to hang out. This was particularly useful for busy grad students who needed something more formal than a chill-hang to get them out of the lab or their pajamas. It started as a half-birthday celebration to get some frozen yogurt together, but we found any arbitrary reason to hang out: Summer solstice, a pet's "gotcha" day, go out to wear our latest new clothes, etc. Make a Google Calendar or a Partiful or whatever to turn it into a silly excuse for an "event."

The "Buddy Errand"

This is a tough one to execute, but sometimes running errands together is an easy way to extend time together. I had brunch with a friend and then extended it by going with her to run a 40 minute errand. I probably wouldn't START a hangout by asking someone to run an errand with me, so I'd characterize this more useful as an "extension." This especially doesn't work for high-cognitive errands like grocery shopping.

I think dragging a buddy with you on an errand from the beginning requires a bigger kind of errand, like driving to East/South Bay to pick up something from Craigslist or IKEA. A lot of quality conversation gets done in the car. Just make sure you treat them for coming with you.

Sometimes I combine this with The "Pop-In" and say "hey, I'm in your area running an errand if you wanna come with me to catch up!" (I always offer the alternative, to just hang out after my errand).

Bonus tool: Catchup app

I use the Catchup app to remind myself to catch up with the friends that I don't naturally text often – the kind of friendships that need a little more management. I set 3, 6 or 12 months reminders to catch up with them.



Related Posts

Members Public

Beats, blood, and blackness

The Kendrick v Drake beef is over. Kendrick won, handily. So why am I still thinking about it? It seems that everyone I talk to is either really invested, or not invested at all. To those of you who can’t stop thinking about this (like me): why is that?

Beats, blood, and blackness
Members Public

Forget gratitude journals, try chain journaling

I invented a new form of gratitude journaling, called chain journaling

Forget gratitude journals, try chain journaling
Members Public

A letter to the people who nearly crippled me

1: observations At 12:59 PM PST on March 11th, 2024, you violently swerved your white sedan into the bike lane that I was in. Luckily, I managed to skid my Lyft bike to avoid your car pinching me against the other parked car on the right. In my rage,

A letter to the people who nearly crippled me