When I saw Danielle Baskin and Tucker Bryant post about the third installment of SFO Flight Roulette, I thought I’d missed the deadline for participating. I signed up anyway and convinced myself I didn’t have a chance.

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Plus, my weekend was booked. I had tickets for a screening of “The History of Concrete.” I’d accepted calendar invites for Muni’s 55 Wine Line Progressive. I still believed I’d stay out late enough to catch Crystal Methyd at Oasis.

Did I even have time for a last-minute trip?!

My boyfriend convinced me to take a breath and go. “Those things will happen again. This won’t.”

In the spirit of spontaneity, Flight Roulette has no schedule. You never know if or when the next round will happen.

So, when I was picked for September 2026, I put my weekend on hold. I packed a carry-on and went to the SFO Aviation Museum & Library.

I wasn't going into Flight Roulette completely oblivious. I'd previously read about the project in the SF Standard and had signed up, but wasn't chosen, for round two. Most of the other 15 to 20 participants either had friends who'd participated or had verified the project's legitimacy after watching an Instagram Reel.

Once we arrived at the airport, Danielle and Tucker took the group on a pre-security tour of unexpected SFO attractions: a hallway of free, working pay phones, a lowrider bikes exhibit and a micro movie theater.

A photographer and a journalist with press passes documented and interviewed the group. The photographer commented on how calm and stress-free the vibes were, considering the unknown. He thought that, given the time constraint, it would be like an episode of The Amazing Race. His observation wasn’t wrong.

As the airport tour continued, the group became less and less anxious. The excitement was palpable. Sure, we were forgetting each other’s names. But we were having fun. We recalled and shared the reasons we were at SFO without a plane ticket on a Friday night.

There were a handful of women in their 30s who’d just left corporate and were figuring out what was next. A man who came back from his first vacation in five years only to be laid off work the next day. Those hoping relaxation would cure their burnout. Individuals who craved the chance to travel solo.

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All of us with one thing in common—the desire to escape. At least from Friday, September 25, to Tuesday, September 29.

A previous Flight Roulette winner whose experience going to Barcelona left a lasting impression joined us just before a winner was announced. She assured us we’d have a whole community of current and past participants to lean on.

For the last activity, Danielle and Tucker had the group play Sardines, a reverse version of hide-and-seek, in baggage claim. It was ridiculous and effective in getting us out of our own heads.

Then, the winner was called.

The losing strangers regrouped. We listened to the winner’s needs, fears, wants and wishes. Then, we spent an hour populating a Google Doc and booking her a trip to Fiji. A direct flight, island-hopping and snorkeling included.

My first job in corporate social media was in 2014. I pitched and drafted Buzzfeed-style listicles for food brands like Reddi-wip.

The portfolio that got me the job was a Chicago pizza blog a friend and I started out of the listlessness of having graduated with hospitality and liberal arts degrees in the early 2010s.

In the 12 years since, I’ve continued building a career in social media.

I’ve watched the landscape evolve from Ashton Kutcher’s Twitter updates to brands as publishers to Cambridge Analytica to platforms as community hubs to short form videos to live shopping to creators to influencers. And, yes, I am exhausted.

For better or worse–every iteration of social media has had one thing in common – people.

Until now.

Like the internet, social has been fundamentally defined by the principles of intrinsic connection. Its purpose has centered around human affiliation, communication, shared values, beliefs and expressions.

We can debate if the benefits of social media outweigh its societal pitfalls. We can acknowledge that social media has expanded our circle of “parasocial” relationships at the expense of our actual social relationships. We can complain about brainrot and doomscrolling. And we can admit that being “chronically online” isn’t a flex, it’s a red flag.

But, if the internet is dead, can it still be a space where we find and foster human connection?

Admission is the first step. The AI era is here. Robots are shifting how social media functions. But I believe humans still shape and define the principles of social media.

Robots and algorithms can continue to control how the social platforms work. But people dictate how social behaves.

As cynical as I may be, I believe people’s behaviors are best when they’re having fun. Having fun is a breeding ground for authenticity and connection.

These weekly roundups are my attempts to prove to the social media industry and myself that scrolling for fun on an internet of bots is still possible.

If you believe the internet should be fun, please subscribe.

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