In an homage to spontaneity, 13 hopeful travelers — all strangers to one another — gathered the Friday before Labor Day at San Francisco International Airport for a gonzo game of roulette.

One of them would win an all-expenses-paid trip to an unknown city. Details of the trip, including the destination, would be chosen by the rest of the contestants. There was no fee to participate, aside from the cost of their time, which would potentially include many hours of travel and a few days somewhere in the world — hopefully somewhere beautiful.

The lottery was organized by local keynote speaker and poet Tucker Bryant and performance artist Danielle Baskin, who has gotten past attention for setting up a campsite at an annual business conference and giving her drone a Tinder profile. The two organizers connected at an event a few months ago and shared their mutual love of public-private spaces like SFO. When Baskin described her idea for Flight Roulette, inspired by an experience of friends surprising her with an airplane ticket, they decided to give it a go.

When the participants arrived, they were assigned a number, written on a small piece of paper, to hold onto. A corresponding number was placed in a bag.

But first, the participants, some of whom dodged a smoke-filled BART train that afternoon, were encouraged to enjoy the wiles of the airport. Go on, they were told: Scamper around the terminals with your luggage. Like first-graders on a field trip, the 13 strangers stared up at the otherworldly murals, dialed one another on the airport’s payphones, and played an alternative version of hide-and-seek.

Outside of baggage claim, Paul, a man working the airport’s information desk, was tasked with pulling the winning number out of the bag.

“There’s so much tension right now,” said one participant as she waited, clutching her number close to her chest. Some were recording videos for Snapchat, others for TikTok.

“Eleven!” exclaimed Paul.

Thirteen sets of eyes darted around the group before Karson Elmgren, a 32-year-old AI policy researcher, revealed himself as the holder of the magic number. With a chuckle, he said he regretted that he would have to cancel a tea party he was supposed to host that weekend.

The details of the weekend trip were to be decided by the losers, who were nonetheless eager to vicariously experience Elmgren’s victory. They gathered in a circle in the airport lounge outside security, opened a shared Google spreadsheet with various flights that were leaving that night, and locked in.

“I love long flights,” exclaimed one participant, enthralled in the depths of planning, scrolling Google Flights, meticulously thinking about where in this huge, enchanting world they could send Elmgren.

They checked his social media pages. Where had he traveled to before? What was his vibe? Did it even matter? Aren’t serendipity and randomness what travel is all about?

They split into groups to come up with a few potential domestic and international destinations. A handful of nominations went up for a vote. They had to choose between round-trip flights that would get Elmgren back to San Francisco in time for work Tuesday morning — as he’d requested. All proposed flights cost less than $1,100 round trip: Charleston, South Carolina; Manila, Philippines; Vancouver; Salt Lake City; and Madison, Wisconsin.

After some debate, the losers chose the most far-out destination possible: Manila. Elmgren would have a long-ass flight, but that’d be OK. He’d have two full days to mob around in the Philippines.

For the next hour or so, the losers booked accommodations for Elmgren. They gave him food and experience recommendations through a shared Google doc he would receive upon his arrival, such as visiting the world’s oldest Chinatown. 

Sitting against a pillar in the airport, texting friends about this absurd thing that had just happened to him, Elmgren would later state that he was nervous about going on the trip — experiencing all the general anxiety a person gets before they travel, condensed into a single moment. He was alarmed at finding himself at the mercy of strangers. 

Twenty-seven hours later, after a three-hour layover in Seoul, Elmgren touched down in Manila.

On a Signal group chat with the losers, Elmgren reported in real time on his little adventures, like learning Filipino swear words, hanging out with local teenagers, and petting stray cats.

He recalled to the group his arrival in Manila. “Getting out of the airport, it’s immediately obvious that this is not a rich country (and I realized how long it had been since I’d been in a lower-income country), and I was a bit concerned that the trip might end up being kind of sad and unpleasant,” Elmgren texted. “And it was to a certain extent, more so than many destinations would have been, but that was also probably the most meaningful and valuable part.

“It definitely hits different to have children come up to you with outstretched hands saying, ‘Bro … food.’” Though he’s from San Francisco, a place known for people living on the streets, Elmgren remarked how odd it was to “see very very thin elderly people laying around on the streets.”

Another surprise: “just the degree to which kind of everything was in some state of apparently halted construction, lagging repair, or just decay in large neighborhoods.”

Other than making these observations, Elmgren visited as many bars, rode as many alternate versions of transit, and befriended as many locals as he could in his less than two days in the country. Multiple people asked him if he knew Tupac.

“Nice quick jaunt that was,” Elmgren texted the group upon his return to the States.

Bryant and Baskin used their own money to sponsor the event and hope to do it again with contributions of around $50 from each participant.

“Flight Roulette won’t give you your dream vacation,” Baskin said after Elmgren’s return, “but hopefully it’s a beautiful experience where you have to learn stuff, navigate the unfamiliar, feel like you’re in a crazy dream, and find gems and experiences that you’d never know just from researching a place on your own.”

Baskin added that while she has ideas of what can be improved for next time, she knows that each iteration of Flight Roulette will be different, “co-created by whoever is brave enough to show up.”