Some thoughts on my first Monday in San Francisco: on exploring a new city, meeting strangers, and more.
Me: “So, what are you doing at the bar?”
Guy I met 42 seconds earlier: “Honestly? I hate flying, so I figured I’d drink four beers before this flight to take the edge off. I fly… maybe… once or twice per year. Probably a bit more now that my mom moved to Tennessee, but I hate it. Just think about it: you’re in a tube, 30,000 feet in the air, sitting there, completely at the mercy of turbulence. Last week, a plane landed upside down in Toronto. And another plane crashed into a helicopter in DC. And there was a near miss somewhere else. So yeah, I’m here to drink before this flight, because flying sucks.”
A few years ago, I spent the better part of a year backpacking Europe (as any 24-year-old with a hellish case of wanderlust should), bopping from city to city each week and staying in different hostels along the way. By week five, I had developed a pretty good strategy for navigating new cities:
After dropping my bags off, I would:
Find a suitable gym in my immediate vicinity, and if a gym weren’t available, some sort of outdoor pull up bar.
Spend no less than five hours walking and wandering to get a feel for the city, noting any interesting bars, restaurants, cafes, or interesting areas I might want to circle back to later.
Return to one of those bars that I had spotted earlier for dinner, sit at the bar, and strike up a conversation with whoever is sitting next to me.
By following these steps, I could stay in reasonable shape, gain a surface level understanding of the city and identify places I may want to visit later in the week, and make a new acquaintance which would, at worst, lead to a novel conversation with a stranger who could provide a few tips about the area, and at best become a friendship, fling, or valuable professional connection (all three of which have, to various extents, happened in the past).
I moved to San Francisco last Sunday, and, while moving to California is a bit different than staying at a hostel in Sevilla, the new city dynamic is pretty similar. In fact, as a side note, this move to San Francisco was a bit too reminiscent of those 2021 travels:
In 2021, I was, more often than not, hungover upon arrival to a new city thanks to antics from the evening before in the previous city (hostel-bound travelers have a real propensity for exploring their shared city’s nightlife options together).
The night before flying to SF, an afternoon in which I intended to pack my clothes, run errands, and chill was replaced by a Guinness-filled side quest through several of Prince Street’s finest bars after my boy Juan Cruz stopped by to “hang for a few minutes and grab coffee” before I left. JC, I love you, even if you did Trojan horse me by offering to “tag along” for my errands before casually asking if we should “grab just one beer.” Which I was totally cool with: I love exploring Prince Street’s finest bars with my friends.
To pile on top of that, a chill “going away dinner” quickly became a “2 AM at this new club called Cosmo” kind of night because, again, it was my last night in New York! Might as well prolong the time spent with friends, no? My first thought, when glancing at my watch and seeing that it was 2:27 AM on Saturday evening, was “Damn, I still have to pack everything, my flight is at 3 PM, and tomorrow is going to suck.” But because time spent with friends is always worth the consequences of spending time with friends, I stoically accepted my hangxiety-filled packing session and flight on Sunday.
So anyway, I moved to San Francisco on Sunday. I didn’t know a thing about San Francisco, other than that the Tenderloin District apparently makes Aleppo look like Singapore and there are self-driving Waymos (which are sick) everywhere. So, after work on Monday, I embarked on my tried-and-true method for getting to know a city:
I walked everywhere, I hit the local Equinox (my membership auto-renewed in December so it’s fortunate those exist here), and I went to a bar across the street from my gym for dinner.
The key to picking out the right bar for dinner is finding one where the food looks good, but not “Michelin Star” good, the locals put some effort into their appearance, but not sport coats and dresses, the venue is at approximately 80% capacity, and the bartender is old enough to call you “son” without it sounding like an insult, but young enough to remember your drink order.
So, post workout, I strolled over to Perry’s on Union.
Perry’s is a perfect bar. It has dog-friendly outdoor seating, checkered tablecloths that are just a bit too nice for the interior, bar seats with backs on them (stools are horrible for lumbar support), Guinness on tap, framed, signed pictures of C-List celebrities, a burger too large to easily fit in your mouth all at once, and, importantly, bartenders with grey hair wearing dress shirts, ties, and aprons. It’s the type of place that Don Draper would go for lunch when he wants to avoid the types of places that he would normally take clients.
I rolled up, post-workout in a hoodie and hat, and luck would have it that one seat was available at the far side of the bar, next to a guy who looked to be 10 years older than me and was somewhere between beers two and three.
I walked over, glanced at the seat, and asked, “Anyone sitting here?” To which my soon-to-be friend replied, “You are!”
It was after exchanging pleasantries that my new acquaintance, who we’ll call “Fred,” discussed with me his existential fear of flying that I noted in the beginning of this blog post. Fred and I bonded over our mutual fear of aviation: I had personally tried everything from IPAs to Xanax to sedate my fear of flying a few years ago, but, for me, the only cure was flying so many times in a single year that I had no choice but to get over it. By your 25th flight in as many weeks, you find yourself thinking, “Turbulence still sucks, but if the last 25 flights didn’t crash I’m probably fine.” And then you aren’t scared of flying anymore.
Taking the bartender’s advice to order the burger (which slapped), I asked Fred, between bites of beef and fries, about his life and career, and he answered, between sips of beer three and four, how he had spent most of his career as a criminal defense attorney before pivoting to estate planning. We chatted about the differences between New York and San Francisco, my reasons for moving out west, advice on getting over one’s fear of flying (I recommended booking like 20 roundtrip flights back and forth between LA and SF to force exposure therapy), and I asked if he had ever found it difficult to represent criminals who were (almost certainly) guilty of some pretty messed up crimes (his answer to this question was excellent), before he caught his ride to the airport.
Then, after dinner, I went to pay, but, having come straight from the gym, I didn’t have my wallet on me, and because this bar was the type of bar that Don Draper would enjoy, it obviously didn’t take Apple Pay, so I had to run half a mile back to my apartment to get a credit card to close my tab, which the bartender appreciated (while I realize that it is legal to steal $35 of food in San Francisco, I like to support the local economy). And I riffed with the bartender for another 20 minutes before calling it a night.
Not a bad way to spend a Monday evening.
You may be wondering, “Jack, why did you spend your Sunday afternoon blogging about your random antics from last week?
The answer is that, while I write about a lot of things, this blog is, at its core, a glimpse into how I’m experiencing and thinking about the world, and right now, those experiences and thoughts revolve around how I’m navigating a move across the country.
Moving is weird, man. You spend years living a certain way, and you have this half-baked idea of what you think the next few years will look like, but then life introduces an unknown variable that, for whatever reason, you feel compelled to pursue, and you do it, regardless of the geographic implications. So here I am, three timezones and one (hungover) flight away.
But it’s nice to know that, whether you’re in Krakow, Buenos Aires, or San Francisco, a stranger will be willing to tell you about how much he dreads his flight to Tennessee in three hours. So I guess I’ll keep talking to more folks. Thank God I love to talk.
And if you’re in San Francisco, and you’re reading this, let’s hang. I have no idea what to do in this city, but you probably do.
- Jack
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