I enjoy conversations, particularly with people I care about. I also have a social circle which is rather geographically dispersed. This, of course, presents the problem of “how do I stay in touch with people?” Facebook et al. haven’t solved this problem in a satisfactory way for me. Discord / private group chats are fine, but don’t feel socially fulfilling in a way that 30 minutes of even infrequent talking often is.

One solution I stumbled into a few years ago was: Set up recurring 1:1 meetings with distant friends. Yes, like a work 1:1. Yes, with an actual calendar invite with an actual Google Meet link.

This is something I firmly believe is worth spending weirdness points on with the right set of people.

Why?: Twofold. First: Staying in touch with people is easier than meeting people, and friendships/relationships become more nuanced with rich shared context over time. Maintaining older friendships is just obviously valuable. Second: Talking to interesting people is just fun.

On frequency: I find this model works best somewhere in the biweekly-to-bimonthly range. It’s probably better to meet too infrequently than too frequently. This is perhaps unintuitive if the goal is maintaining relationships, but I think it’s better to have a glut of topics to discuss than a scarcity – and as long as you’re meeting every 3 months or so, you won’t hit “reconnection awkwardness” territory.

On duration: 30 minutes is a good baseline to start with. It’s short enough that it’s not hard to schedule into an evening, or a weekend morning. It’s enough time to catch up on life events from the past week(s) or month and to talk through a few substantive topics, yet not too long like you feel like you feel pressure to fill the time. Many of my chats are exactly 30 minutes like a work meeting; some of them are more free-form, lasting for an hour or two depending on the context.

On scheduling, rescheduling, and following through: Some people find it easier (or possible/enjoyable/fun) to stick to strict schedules than others. As a rule, I never get upset if someone needs to reschedule a chat or cancel last minute. The schedule is just a forcing function for prompting some sort of interaction – even if that interaction ends up just being a quick exchange of logistics and pleasantries.

On what to talk about: Normal rules for “having good conversations” apply. Most of the time, the conversation can just be about “what has your life been like recently?”, but also: be a good conversationalist. Just because it’s a remote, structured talk doesn’t mean that it has to be a remote or stilted conversation. Talk about philosophy, ethics, existential dread, your cats/dogs/hamsters, books, annoyances, accomplishments, admonitions, advice, burgeoning hobbies, travel plans, creative hobbies, etc.

I’m writing this post as a nudge in the direction of this being normalized. But also so that the next time I ask someone to set one of these up, I have a handy pointer to send. (Hey, future person! 👋)

Cover: Girona, Spain