Last Month I Had My First Intimate Experience With AI

And maybe you want to have one, too?

The scene of the encounter

Last month, I was back in suburban Boston for a few days, staying in the room where I’ve slept more than anywhere else.

We moved into that house when I was four or so, and to say that the feel of the place has changed in recent years would be a massive understatement. When we moved there in the 1980s, my youngest brother didn’t exist yet. He was born not long thereafter, and for a while the number of living beings residing there steadily increased — first my brother, then a steady stream of pets ranging from hamsters to cats and birds and a couple of dogs. It was always a place with a lot of life in it.

Then my mom died in 2021, and last year we had to move my dad into assisted living. Now the house feels more and more like a museum. Oftentimes my brother is there, or I’m there, or a friend or family member passing through the Boston area is there, but the contrast is still jarring. It’s hard not to head toward Boston from New York without thinking about the dozens of other times I’ve made similar trips, climbed those front steps, crossed that threshold, and been greeted by at least two other members of my family.

All of this was weighing on me during my trip in March. I am deeply rooted to this part of Massachusetts. It is in my bones. I love the hills, the leafiness in the summer, the way the low light glares through bare branches and bounces off the ice in the winter, the occasional glimpse of the Pru when you face the city at the right angle. Greater Boston is and always will be my one true home, and for more than 35 years, that home was anchored by this particular house.

So it makes sense, especially given the circumstances surrounding my visit last month, that every walk or drive triggered memories of earlier years.

This time around, I kept thinking about my adolescence and young adulthood. There’s a lot of sadness there. For a significant chunk of it, I felt unwanted, excluded, and lost deep in my own neuroses. Often, my feelings did not map well onto reality. While I went through a rough social patch in middle school, early in high school I made amazing friends who I still love to this day. It’s genuinely ridiculous how many solid people there were in my high school class, and I know a lot of people far more likable than me who have far fewer high school friends than I do. As for feeling unwanted, that had to do more with girls, and I was incredibly self-sabotaging on that front — no, I was not fending off the ladies in high school or college, but I also wasn’t nearly as unwantable as I had somehow convinced myself I was.

Because I had adopted rigid and unduly pessimistic stories about myself and lacked the experience to put things in perspective, it would have been helpful to talk about all this with friends or my parents. I was horrible at doing so. So in retrospect I was stuck digging a hole, alone, and even years later I find it hard to talk about — at least with full honesty and detail.

That’s where the AI came in.

***

Around the time of my visit, I’d been messing around a little bit with Google’s NotebookLM, an AI research assistant. You simply provide it with documents or other forms of media, it digests said material, and then it can produce summaries, Q&As, and so on. I haven’t yet taken full advantage of it, but I can see it being a miracle time-saver in terms of book research. I could upload 15 recordings of interviews I’ve conducted and then ask it questions like “Remind me who told me that story about eating horse meat in Kazakhstan?” or whatever, and it’ll instantly be able to find it.

NotebookLM’s weirdest feature by far, though, is “Audio Overview.” If you select this option, NotebookLM will take whatever you’ve fed it and turn it into an AI-generated podcast featuring two hosts, one male and one female.

Weird technology collided with a weird moment in my life, so I decided to try something a bit odd. I was at my favorite hometown pizza place, and I took 10 minutes or so to type up a brief but very personal and very specific account of the aforementioned adolescent and young-adult experiences — and then I fed that document to the fake podcast hosts to see what they would make of it.