At the top of sloping streets, the bay windows of pastel Victorians wink down on the Haight.

There is a vintage store on the raggedy end of the street, a real vintage store with real vintage things, prim 1950s swing jackets and Jackie Kennedy pillboxes and square wartime pumps. Those things, and a $40 purple velvet blazer that skims my wrists, just how I like it.

I am waiting to pay when the radio, all oldies all the time, eases into a familiar refrain.

If you’re going… to Saaan… Fraaan… cisco…

At the cash desk, the little brunette with the flowers in her hair (yes, really) flinches, reaches out a long thin arm, clicks the radio off.  

“Fuck that shit,” she says, and smiles sweetly. “Cash or credit?”

I wanted to tell her I’d been singing that song for days, ever since we drove over the Bay Bridge in the blue-blackness of the morning, ever since its garlands of lights lit our way into the city by the bay, ever since we turned down the Embarcadero and smelled the wind on salt water and squinted to make out the Golden Gate through the fog and clapped when we finally did.

The Bay Bridge at night.

Instead, I paid for my purple velvet blazer, and left.

But through her, and others like her, I did learn one thing in San Francisco: maybe Winnipeggers aren’t so unusual. Maybe it’s just that everyone hates where they are from.   

We put this theory to the test one night in the Castro, underneath the snapping edges of rainbow flags. 

The Castro is a living monument of sorts; “you’re in the homeland,” I told my friend. The Castro Theatre is still there; so is the door to the apartment where Harvey Milk lived. The Elephant Walk is gone, replaced, like so many things in this surreal and sunbitten city, with a cheerful memorial to the dead: Harvey’s. (Do try their Harvey’s Sticks. Delish.)

Long after night fell we stalked the streets, blood reeling from a couple of rounds of inexplicably generous California shots, and demanded information. “Are you from San Francisco?” we asked, to everyone in particular.

Most are not; we met a tall goddess with a glorious ’70s Afro. She moved from Brooklyn last year. We met a bouncer from Hawaii. A student from Philly. Cab driver from Jamaica. Everyone from everywhere else.

When we finally stumbled on the natives, we were almost convinced that nobody from San Francisco is actually from there. But our new, born-and-raised friends were obliging of our only question.  

“What’s it like, living in San Francisco?”

One by one, they screwed up their noses, stuck out their tongues in the universal gesture of distaste. “I hate it,” one man said. “I want to move to Canada.”

Another waved an arm over 18th Street. “San Francisco is over,” he said.

My real question left unspoken: I never ask them what it’s like to live in a city frozen in time, its mythos enforced by psychedelic star maps and the burden of its own history. 

I found Jim Jones' house and Patty Hearst's hideout!

San Francisco’s mystique is a widow’s wedding gown, salvaged and smoothed by decades of hands. Still picture-perfect, brightly beaded, and pristine. Still ready to be romanced. Her lover is gone, and he won’t be coming home again. But she still remembers.

That is a lot of expectation for the people of a city to bear: the dreams of a nation, of a species even, dreams of love and romance, of passion, politics and art. Dreams that are now realities in some other place.  

Guess what time it is at Haight and Ashbury?

I can assure you it was not 4:20 when this photo was taken.

“Fuck that shit.”

I started to understand why so many of the locals said they hated it there.

Actually, maybe I still don't get it.

But that was San Francisco. Our trip took us somewhere else: Portland, Oregon, a city both beautiful and somehow new, a city bursting with fresh potential, a city that believes in itself as something still being made.

It is also, I might add, a city to which Winnipeg can more reasonably compare, contrast and learn from. But it is also a city that spawned so many constructive blog ideas, they must come one at a time. Patience. I say this for myself most of all — I want to tell you all about it.

Teaser: there will be donuts. Donuts that travelled 3,000 kilometres home.


One beautiful thing did happen that night in the Castro. That morning, while getting ready to visit Alcatraz, I learned via text message that I had been nominated for a National Newspaper Award in the Long Feature category.

There are few words to express what that means to me, or how surprised I was to be nominated, and in a category that speaks so much to me as a writer, and for a story I’ve been wanting to tell for a decade. I can’t thank everyone enough for their kind words about it.

I celebrated that night with our one-night-stand of San Francisco friends, mere feet away from Harvey Milk’s apartment and the old site of his famous Castro Camera. After a few libations, I imagined that Harvey’s ghost approved of my nomination, and my joy.

Friends, it can be a beautiful life we lead. May you all find your own night in San Francisco.

All photos on this page taken by Josh Kolesar, March 2011.

  • Walter

    Congratulations on being nominated!

  • Melissa

    Thanks so much! I am just so blown away by it. And planning my next long feature now, haha. It’s just so awesome because long features are definitely where I fit in, I guess, or at least what draws me the most and what suits my skillset the most, so this is a real honour.