Serendipity Log v.1

This whole thing is so improbable, guys.

Mar 21, 2025

Twenty years ago, my Mom gifted me a copy of “I Thought My Father was God” - a collection of true stories from NPR’s Story Project as documented by Paul Auster.

The book is full of wild coincidences and serendipities. And it changed me. Until then, I hadn’t really ever heard stories that defied logic or probability. It alluded to a world out there that might be weirder than I had yet to encounter. A world I wanted to live in.

For example, Lori Peikoff recounts:

In the 1970’s, Joe is seated next to a woman at a restaurant in NYC, and they hit it off. She gives him her phone number, which he then loses. He tries to find her at her job, but can’t. Later that year they both travel to Europe, and once again they find themselves—you guessed it—seated together at the same table. They fall in love, get married and have a child, me.

Depending on where you fall on the Woobric1, serendipities are either statistical anomalies, fun coincidences, or whisperings from The Universe that you’re on the right path.

I don’t know what I believe, but I do like the version of the world where I’m more aware of serendipitous happenings. I’ve been thinking about logging people’s stories because cultivating awe at the sheer improbability of all the things feels helpful right now. And we all could probably stand to see the universe as benevolent, if only occasionally. so.

Writing about serendipities is an art form that I need to practice. Unless it’s a top-tier, undeniably insane story like the star-crossed restaurant lovers, you have to structure things in a way that really lets the anomaly shine and the significance land.

So let’s practice! Here are minor little ones that have happened to me recently:

Dopplegang

I have a few doppelgangers in the city.

Over the years, many people have sent me photos of people they thought were me. They’re always a little off (“You think that’s what I look like?!”), but people swear that they have my essence.

The idea of a ‘double’ has always felt interesting to me. Based on these texts I used to get, I once sold a television show called “Doppelgang” about a guy like me who meets his cooler doppelganger and teams up with him to take on life as an odd couple duo.

It was the fantasy of what I wanted to happen. But the show didn’t get made. And I’ve never met any of my doubles.

And then, one day, I’m sitting in my favorite breakfast spot, and my spitting image sits down next to me and starts talking to me as though we were old friends. Is this my restaurant story?!

I can hardly believe it. His name is Sascha and we have a strange and hilarious chat without ever acknowledging the absurdity of the situation. He gets up to leave and says “Well, I’m off to officiate my first wedding. Wish me luck.”

We don’t exchange information, and he disappears onto the street.

But in a matter of weeks, he starts showing up everywhere. First, in a coaching co-op I’m a part of. Then, on my Instagram feed. And then, in conversations with friends who apparently know him.

And then, I get asked to officiate a wedding. The first I’ve ever done.

As I’m standing at the podium, I look out into the crowd of 300 strangers, and I see one person I definitely know.

A bearded ginger smiling back at me.

On the dance floor, I go “Sascha! Isn’t this crazy?!”

And he goes “Not really.”

Across the Street from Fancy

I’ve been thinking a lot about the people I’ve met in the first half of my life. I’m curious about things you can’t learn on Facebook or Linkedin. I want to know what those moments where our paths crossed meant in their timelines.

What happened to that kid who lost his finger in a camp boating accident who never returned? Did that girl I dated from MySpace who was obsessed with serial killers ever get over that? Was that theatre director who always had a harem of young girls around doing something nefarious?

I also think about people that I actually knew, like my freshman-year college roommates. We had a wild experience transitioning from our families of origin into city living, and I’m dying to know what was really going on for them during that time and where life took them. A reunion has crossed my mind, but I’ve never done anything about it as I don’t have contact information for half of them.

Last week, my wife and I had childcare and decided to go on a rare date night. I looked up Eater where the kids are going these days. For some strange reason, I felt called towards Eleven Madison Park’s new cocktail bar. It didn’t make any sense; it’s not really my thing, and we had theatre tickets that were nowhere near the Flatiron District.

I couldn’t get a reservation, but I decided to show up anyway. Also not like me.

My wife gets there first, and they tell her it’s all booked. She opens the Google and sees that the hotel bar across the street is supposed to be decent. I feel pretty bummed, but we’re running out of time, so I reluctantly agree.

We go to the hotel and have perfectly decent dirty martinis. In walks my college suitemate on a first date. In my twenty years in New York, I’ve never run into this guy. We hug and exchange small talk, and I off-handedly mention that we should have a reunion, and he goes, “I would love that.”

I email the one roommate whose email address I have and one by one; we track down the gang of six. Now we’re working on getting a reunion on the books in May.

All because I felt drawn towards a bar I couldn’t get into.

The Monkey

My wife and I met on OKCupid, and we had zero mutual friends. Over our decade together, that has continued to hold. I once took a meeting with someone she went to High School with, but that’s the extent of it. We come from different worlds. A real internet success story.

This summer, I’m camping with some of her friends. Around the fire, this guy Michael brings up the idea of having a monkey as a pet. My wife mentions that I briefly dated a girl whose family raised a monkey as a sister.

This is, of course, perfect campfire fodder and leads to all sorts of follow-up questions (Was that weird? Yes. Did the monkey like you? No. Did the monkey ever catch you hooking up? Yes.)

Someone asks what kind of parent would decide to do this, and I explain that her mother was a nurse at a zoo, and her father was a folk singer who had some success in the UK.

And I hear a voice with a British accent go: “Wait. Is her Dad’s name Dean?”

”Uh, yeah. How did you—”

"—My Dad was a fan and named me Lydia after his song. I just delivered a painting to him recently.”

I guess we now have one mutual friend. Two, if you count the monkey.

Maybe the world isn’t as small as it used to feel, but it’s certainly full of strange, magical moments if we’re willing to notice them. I don’t know what I believe, but I do believe in paying attention when the improbable happens.

Do you want to hear more stories like this? Do you have any serendipitous stories worth sharing?

Or maybe...

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