It’s a Victorian-house-turned bar, and we’re sitting on the third floor around a coffee table. The girls just left to get more drinks, and although it’s 6:30 p.m., he’s got his single-serve french press and I some red wine, so we stay. I met him five minutes ago and, prompted by the music overhead, he asks me what I think about the Michael McDonald years of the Doobie Brothers.
And in this moment, I am unsure where I am.
Portland, it seems, is not that far off from Portlandia — the place “where young people go to retire” who riot against Trump’s victory and eat crazy doughnuts. A city stuck in the 90s populated by the young yearning to stave off old age by staying hip and keeping weird.
Distinguishing between the two places proved to be quite the challenge.

Speaking to the youngness of Portland (and Portlandia) is it’s size relative to other major U.S. cities.
“Seattle is probably 10 times bigger than Portland,” a local Lyft driver says. My friend Jasmine, who called Santa Cruz home prior to moving up to Portland, would also echo the “small-feeling” of Portland.
But what’s funny is that Portland isn’t actually that small. Matter of fact, even if you factor in Seattle’s massive water-covered area, Portland is larger.
The Portlandia mentality, it seems, has the power to turn misinformation into truth. To make Portland seem small even though Denver, Philadelphia and Detroit are acutely similar in size.
A real-life Portland landmark perhaps contributing to this small-city mentality is Mill Ends Park — the world’s smallest park.
Mill Ends Park used to be a 24-inch diameter circle in the middle of a median along the Pacific Highway where a utility pole once stood. Now, it’s basically the exact same thing, with the exception of a little added lore courtesy of an Oregonian newspaper writer who talked about leprechauns and the like. The park boasts a square footage remarkably close to Pi (3.138 ft2 to be exact), and if you didn’t know it’s a repurposed utility hole, you’d surely miss it.
Repurposing things, as also evidenced by the Victorian-house-turned bar, is surely Portlandian.
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Another thing distinctly Portland (Portlandia?) is a love of vinyl.
I ordered a cup of coffee at Courier Coffee Roasters downtown, and while waiting for them to grind the beans and make it via pour-over, I heard the music overhead stop, and glanced over to see a barista flipping a record over.
Cute, I thought. Kitschy even. Perfect for an independent coffee shop.
However later in the night, I had traded in my coffee for a glass of whiskey at Dig a Pony, a dimly-lit fanciful bar which serves “upscale cocktails and varied nibbles” as Google puts it.
And then, sure enough, I hear the music overhead stop, and glance over to see a bartender flip a record over.
Coffee or cocktail, Portland loves their vinyl.
“There’s record stores opening in Portland,” my new friend at the Victorian-house bar says. Matter of fact, within the last four years, places have opened which give Portland residents the ability to produce a vinyl master and then mass manufacture all within the confines of the city.

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Speaking of the Victorian-house bar, the girls have returned with their drinks, and we are then joined by a middle-aged couple who affirm the notion that the lines of Portland and Portlandia are blurred.
She tells us she’s 40 years old but she could easily pass for 25, and I’m unsure if her blonde side ponytail speaks more to the older age or the younger. She wears her fiance’s old wedding ring from his previous marriage around her neck. One of the group wants to go outside to smoke and is surprised to learn she no longer smokes — now she vapes. An apparent New Year’s resolution.
He sits down and within minutes, we start talking about guitars, and I am again unsure where I am.
Music, guitar-talk, doughnuts, repurposed things, side ponytails, and a small-city feel from a major metropolitan area. Portland has it all.
Just don’t get lost in Portlandia.