06/17/2025
I have kept up with a good friend, Jill - not her real name - over the years, lauging , crying skiing and having lunch. Over lunch today, I sat across from Jill whose stories tumbled out with the same wild energy as her two cats, who’ve apparently taken a liking to chewing holes in her favorite clothes. Between bites of salad and bursts of laughter, we bounced from the absurdity of feline fashion sabotage to the delicate politics of high heels and work attire. Before I knew it, the conversation had taken a sharp turn toward my love life, and suddenly I was the one being dissected—gently, curiously, as only Jill could manage.
One of the most useful things Jill and I have done together to deepen not just our friendship, but also how we relate to others in our intimate circles, is spend time studying Getting to Zero by Jason Gaddis. It’s been a kind of shared compass, helping us navigate emotional tension and miscommunication with more honesty—and fewer apologies for being human.
Today, Jill threw down a challenge: not stay silent in one of my closest relationships—not to shut down, but to truly listen. When I tried to wiggle out of it with my usual arsenal of well-rehearsed justifications, she wasn’t having it. Her silence in response said more than words, and I felt the lesson land.
The topic that really got me thinking today came when we found ourselves circling the question: Does AI in one-on-one communication make us inauthentic? I argued yes—absolutely. To me, there’s something inherently dissonant about outsourcing intimacy, even in the form of convenience.
Jill pushed back, saying AI could actually enhance relationships by freeing us to focus on emotional presence rather than logistics.
I brought up the "AI secretaries" at work—those bots that summarize our Zoom calls with clients. I had read through one recently and felt nothing but detachment. It had neatly packaged an hour-long human exchange into bland bullet points, but stripped of tone, nuance, and human presence, the summary felt hollow. Worse, it felt unbelievable. Like a ghost story told by someone who had never seen a ghost
Let me know what u think or AI, or even an experience you've had.