If you use software to help you be a better friend, have you failed?

That seems to be what some people believe, if the tweets in response to Kaitlyn Tiffany’s (🐦) story in the Atlantic are any indication.

In Managing Your Friendships, With Software, she writes about several startups whose apps appear to be overtaking the productivity category of the App Store as people seem to be looking for assistance in caring for and attending to their personal relationships:

There’s Dex, “a tool to turn acquaintances into allies.” Clay, “an extension of your brain, purposefully built to help you remember people.” “Forgetting personal details?” Hippo “helps you stay attentive [and] keep track of friends, family and colleagues you care for,” for just $1.49 a month. Plum Contacts sends reminders to message your friends, and rewards you with cartoon berries that “indicate how strong your relationship is.” “Build the relationships you always wish you had,” the UpHabit site promises.

Among the tweets gathered by Techmeme, these stood out to me:

(Authors, in order: Nick Prudent (@xecretcode), __anoop , Ellis Hamburger (@hamburger) , Rachel Wilkerson Miller

Twitter is rarely a reliable source of insight or deeply considered rebuttals. I, too, have blathered inchoate snark in response to baiting headlines in the past too (though I try to abstain from the habit myself).

These tweets caught my attention because I can relate to the problem Dex et al are tackling. The critiques also echo those once lobbed at Molly (RIP). With Molly, I wanted to build an artificial intelligence that supported an individual’s ability to build, manage, and nurture relationships in the digital era. Personally, I found that as more of the people I cared about shared information about themselves online, my ability to consume or make sense of it all couldn’t keep pace. I needed help — and came to believe that the anecdote for social technology overload might actually be more social technology.

And makers of these apps may have come to a similar conclusion, if you consider what Romy Lynch, co-founder of Monaru, had to say:

Our hunch is that there are more people out there .. who need a little help to bring focus to them and to make sure the important things are remembered. We want Monaru to be your new Superpower 🦸‍♂️, a tool that gets rid of the anxiety around remembering or planning and lets you focus on the important part: connecting.

Just a few years back, it was an accomplishment to compile and maintain an up-to-date address book of contact info about your friends. But with the migration away from feeds to messaging, nearly everyone these days is available via several on-demand channels (SMS, iMessage, WhatsApp, etc). But although you can message your friends to inquire about their activities, the promise of social media feeds was to make gathering such updates a passive, asynchronous affair in which the burden of dissemination was placed on the actor herself, rather than on the consuming audience. This way, the actors could be the authors of their own narratives, and keep efficiently keep each other apprised of our goings on.

But with the decline of the newsfeed (brought down by the declining veracity and authenticity of its contents and contributors, respectively) we’re shifting the burden back to the audience to show up for ephemeral updates that vanish after 24 hours. To stay ambiently informed of our friends’ lives is to stayed glued to their stories on our phones, lest we miss their surprise wedding in Bali or their days long life-affirming trek to the arctic.

With the migration to ephemerality, we’re tacitly giving up the archive of our collective memory. No longer can we jog our memories of that trip we took a couple years ago by searching for the corresponding posts or photos. The more we pump data into the stories black hole, the less our friends are able to refer, reminisce, or recollect information from our shared past. In turn, this increases the need to sustain interaction and maintain constant communication, so that we don’t slip out of those four vaunted slots reserved only for those with whom we interact most:

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The stables of the Four Horsemen of the Friendship Apocalypse

For some, this might be acceptable. For others, depending on the size of their social circle(s), they may not even notice as friends drop off.

But for me, having developed and maintained many relationships both IRL and digitally over the last decade, this creates a predicament. Without a reliably accessible store of authentic and historical social content, there becomes a ceiling on the number of relationships I’m able to juggle simultaneously as well as those I’m able to revisit and revive later (i.e. “hey, remember that time when we went to [insert obscure but super fun event here]?”). Maybe that’s as it should be. Maybe there should be a temporally enforced limit to our ability to maintain relationships. But I’m not ready to acquiesce.

As I’ve embarked on my nomadic journey this year, I’ve benefited greatly from connections that have lain dormant for years. It’s clear to me that the value locked up in my connections is massive, yet so few tools exist to help me inquire into (i.e. search for) or discover (browse) hidden commonalities and connections in the data that’s been shared with me.

And so I suppose that’s where the apps in Kaitlyn’s piece come in. Instead of relying solely on the social data of my friends stored with third parties (the purveyors of which may change or restrict access at their whim, or may disappear altogether), these personal CRM apps (or PRMs, actually) give the individual greater sovereignty over the storage, recollection, and enrichment of their personal and social memory.

While Axios writer Kia Kokalitcheva may find “something deeply unsettling about the idea that a friend is reaching out only because an app reminded them to” because “it’s hard to believe they truly care about you”, if my intention to follow up was fulfilled thanks to having augmented my memory with one of these apps, the momentary disappointment of confronting the limitations of my wetware would’ve been worth it.

I simply don’t buy that the use of software to manage or enhance relationships trivializes them, or demonstrates some failing in one’s humanity. To the contrary, now that we have built the capacity to stay in touch with far more people than Dunbar’s number would allow, the only way for us to successfully show up for and nurture those connections is to employ variants of the technology that makes those connections possible in the first place. I understand that we may not be able to carry on uniformly satisfying and successful relationships concurrently, but over time — with additional attention and energy—perhaps we can do a better job, on the whole.

What with loneliness now the greatest health epidemic facing America, it only seems reasonable to equip more people with tools for developing and maintaining better relationships, longer. Technology alone won’t make us better at relationships or becoming better humans, but for many of us, having a little extra help certainly couldn’t hurt.

Inventor of the hashtag. Ever-curious product designer and technologist. Previously: Google, Uber, Molly (YC W18).

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