Caspian started explaining the route on the drive in, which should have been my first sign.
Not the route — the system. The system he had built, over what I can only assume were several late evenings, in a chatbot window, asking an AI to help him engineer the perfect Ramble date. Peak foliage sentiment. Optimal cider window. The exact calibrated moment at which spontaneity would feel most authentic. He showed me the output on his phone at a red light: a bulleted list, timestamped, with a section labeled "Mood Architecture."
I said, "Caspian, it's the Ramble. People just walk around."
He said, "That's what they think they're doing."
So we parked and it was 57 degrees and drizzling in the way that Montpelier drizzles in early October — not committed enough to justify an umbrella, just committed enough to make you aware of your shoe choices every thirty seconds. The downtown was lovely. People were drifting between shops with their coffees, ducking into gallery openings, doing exactly what the Ramble is designed to help humans do, which is linger pleasantly without a plan.
Caspian had a plan.
"We need to hold here for about four minutes," he said, outside a bookstore, consulting his phone. "The AI says we want to hit the State Street stretch closer to 6:20 for the light."
"What light? It's overcast."
"Anticipated light. It was accounting for a possible break in the clouds."
There was no break in the clouds.
We did the loop. Then we did a smaller version of the loop. A couple came out of the bookstore eating little cheese samples from what looked like a paper cup, just radiantly unbothered, and I watched them drift away toward the warm yellow glow of a shop window while Caspian recalculated. He had asked the bot to adjust for the drizzle in real time. The bot had, apparently, suggested we circle back toward the State House for a "golden hour adjacency window," which is a phrase I am still processing.
"We're three minutes from magic," he said.
"You said that eleven minutes ago."
"The magic moved."
Here is the thing about Caspian, the thing that makes it impossible to actually be annoyed for long: he was so genuinely invested. Not performing investment, not doing a bit — actually thrilled by the logistics of it, by the idea that a perfect evening could be engineered if you just had enough data. He had asked the AI about cider timing. He had a shortlist of exactly two cider options ranked by "atmospheric fit." He had thought about this more than I have thought about most things I care about.
At 6:22, standing in a light mist outside a gallery with a poster for something at Lost Nation Theater in the window, he looked up from his phone with an expression of genuine betrayal. "It keeps recalculating," he said. "I think the drizzle is throwing off the sentiment model."
"The sentiment model," I repeated.
"It's supposed to surface the spontaneous moment. But every time I check in, it pushes the spontaneous moment three minutes forward."
I took his phone and put it in my jacket pocket. He looked at me like I'd confiscated a compass in a wilderness he was not equipped to navigate by stars.
"Caspian," I said. "Look around."
He looked around. Downtown Montpelier in early October, Ramble evening, shop lights warm against the grey, someone walking a dog with a little rain jacket on, two people sharing something out of a paper bag on a bench, leaves coming down in the particular Vermont way that looks like the trees are trying to be tasteful about it.
"It's actually pretty nice," he said, like he was reporting this to me from the field.
"Yeah."
We got cider at 6:31, which was not on the schedule. It was good cider. We sat in it a while and the drizzle softened and at some point he pulled out his phone, I think reflexively, and then put it back without looking at it.
"For the record," he said, "the AI did predict this outcome as a contingency."
"Did it."
"Seventeen percent probability. It called it 'unstructured success.'"
I told him sixty-four percent of Americans think AI is developing too fast. He said he wasn't surprised, because most people weren't using it correctly. I did not argue. The cider was warm and we had nowhere to be, which is the only thing the algorithm ever actually wanted for us.