How ChatGPT Booked Me a Haircut... on a Bus

July 31, 20252 min
How ChatGPT Booked Me a Haircut... on a Bus

How ChatGPT booked me a haircut — and what came of it

Today I decided to test out ChatGPT's agent mode. I was inspired by a post where everything went smoothly: someone asked the agent to book him a haircut in LA, it opened a browser, found a place, booked it, easy as that. The post had a suspiciously high em-dash count, but I figured I'd try it myself anyway:

"Book me a haircut tomorrow in the Brooklin neighborhood, São Paulo."

Spoiler: I did not see this level of chaos coming.

First impressions: flawless automation

At first, everything was perfect. The browser popped open, and the agent got to work, cheerfully narrating:
"Comparing ratings,"
"Scrolling the page,"
"Clicking the booking button."
Right on script. It found a salon, started the booking, and asked me what time worked.

It only paused once — to hand control back to me so I could log into the booking site — then carried on by itself and sent a tidy summary: a barber will be expecting you tomorrow at 1pm, the cut takes 25 minutes.

I checked my email and, sure enough, the booking confirmation was there. Fantastic! We've finally arrived at that bright shining future where the only thing AI still can't do is find your matching socks in the morning — everything else, apparently, can be delegated.

The twist: a surprise on the curb

But right before heading out, something made me pull up photos of the place. And there it was: a barbershop inside an ACTUAL CITY BUS.

Not "vintage-inspired," not "converted into," just a barbershop, in a bus, parked on the side of the road. Stools, dust, and an overall vibe of quiet despair.

Well done, AI: mission accomplished.
But had I actually gone, my next request to the agent would've been: "Find out where they sterilize the equipment around here."

Takeaway: double-check even the smart agents

Check everything, always. Human agents and digital ones alike, amen.