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HomeEntertainment

How serendipitous run-ins make San Francisco so special | Lifestyles

June 26, 2025
inEntertainment
How serendipitous run-ins make San Francisco so special | Lifestyles
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Editor’s note: This article originally posted on the San Francisco Examiner. Click here for more culture reporting at sfexaminer.com

The Bay Area is large. San Francisco is not.

There is a common misconception conflating the two, giving San Francisco an outsized reputation beyond what the California Department of Finance estimates is a population of just more than 840,000 people.

It could have to do with our mighty influence on state and national politics. It might be that other comparably notable American cities such as Los Angeles, New York and Chicago boast much larger populations. Or perhaps we simply get under people’s skins in a way that inflates our sense of provincial narcissism.

But this is a city built on a peninsula — so no urban sprawl — with historically conservative housing-development policies in an area totaling fewer than 49 square miles. Despite being a bustling urban center, it’s compact, walkable and socially interconnected — a rare blend that makes chance encounters surprisingly common.

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It’s compact, walkable and socially interconnected — a rare blend that makes chance encounters common.

So, if you live in or around San Francisco, you are going to run into people you know — a lot.

That’s why I call San Francisco “the Run-In City.” It’s the biggest small town in America, where you can’t walk down the street or go to the park without seeing old friends, coworkers or even family members. Anonymity is not a San Franciscan cultural facet, but these run-ins generate something even more powerful — a sense of belonging.

Three personal examples over three consecutive days sum this up especially well.

Last Friday I attended a Shabbat dinner in the Marina at the home of someone I had never met before. I expected to know only the guest who invited me, but within minutes of arriving I was catching up with Sarah, with whom I spent two hurricanes at a hotel in Playa del Carmen, Mexico, nearly five years ago. Kismet, one might call it, in an undeniably San Franciscan flavor.

On Saturday, I marched from Dolores Park to Civic Center for the “No Kings” protest. I arrived alone but ran into a few political friends as the march kicked off. By the time we hit Market Street, I’d given hugs to several other friends I’d spotted along the way, only to fall in with yet another friend group for the remainder of the march. It was a well-attended peaceful demonstration, of course — but still.

On Sunday, I took my dogs to the park, where I ran into my upstairs neighbor, Jill. She informed me that she heard my husky mix, Vinny, howling the day prior. As we stood chatting, another woman arrived with her dog — and asked if Vinny was the one she had seen sticking his head out of my apartment window, singing to her. Three perspectives on a moment in time formed a full story, all thanks to serendipitous timing in the Run-In City.

And these are just people that I already know.

I like to call the next level of this San Franciscan phenomenon, “Two Degrees of Gavin Newsom.” While the rest of the world experiences Six Degrees of Kevin Bacon, I theorize that any San Franciscan is likely only separated from our former mayor and current California governor by two people at most. But any name could be swapped in, and it would still likely apply, because there’s a fair chance that you have mutual acquaintances with many strangers in San Francisco.

That proximity is what makes The City so special. This is the kind of place where, if you have a problem, your friend will know a guy who knows a guy who can fix it, and where people organize coalitions to address what matters most in our community. Although those coalitions can be at odds with each other, the members are still going to run into each other at meetings, events or restaurants, so a certain level of tolerance and decorum is required — or at least it should be.

When I accidentally run into someone I know, or someone who knows someone I know, it makes me feel like I am a meaningful part of the 840,000-piece puzzle.

I don’t think I’m alone in feeling this way. Multigenerational residents and techie transplants alike have reported back to me a similar sense of wonder and whimsy that arises with a run-in, and that it’s basically serotonin-boosting.

San Francisco uniquely offers the joy of serendipity — a reminder that you’re not alone, that your people are close by. It turns errands into reunions, casual strolls into spontaneous catch-ups, or dog walks into hiding behind a trash can from your ex.

These accidental meetings stitch daily life with connection, grounding you in a place that feels both alive and intimate.

Fourth-generation San Franciscan Ali Wunderman is an award-winning travel, food and culture writer. She lives in Nob Hill with her two rescue dogs and can often be found at John’s Grill enjoying a dirty martini.



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