This story is part of Victorian Secrets, an ongoing dispatch from The Bold Italic on sex, dating, and rent control in San Francisco. Names and identifying details have been changed to protect the innocent, the guilty, and the emotionally unavailable.
Forget the fairy tales. In San Francisco, romance dies at the hands of the SF Municipal Transportation Agency.
We live in a 7-by-7-mile grid where an unregulated parking spot is a hotter commodity than a matched 401(k). You can have the perfect chemistry, flawless banter, and a shared passion for natural wine, but none of it matters if he isn't willing to fight the local zoning laws for you.
I had been dating Caleb for six months. He was the holy grail: he worked in fintech but—crucially—never once brought up his stock portfolio at dinner. He had a rent-controlled apartment, a full head of hair, and an uncanny ability to secure reservations at The Happy Crane. We had survived the logistical nightmare of taking BART to an Oakland warehouse party on a Saturday night. We had even survived a weekend getaway to Guerneville without a single argument over the Spotify playlist.
Caleb didn't just have the apartment. He had a vintage Volvo and the willingness to be the designated driver for the last leg of a wine trip. We had spent the afternoon working our way through one or two tasting flights, and soon we were gliding back down the 101-South. But the second we hit the city grid, we faced the very punishing reality of Mission District parking on a Sunday night at 11:00 PM.
We weren't just two lovers returning from wine country. We were hunters. And our prey was a nine-by-eighteen-foot rectangle of unregulated concrete.
"Take a left on 20th," I murmured, my face pressed against the passenger window of his vintage Volvo. We were dodging the endless parade of double-parked cars with their hazard lights blinking outside the taquerias, creating an obstacle course of late-night burrito runs. I was wearing my favorite pair of vintage boots from Held Over—fabulous for a tasting room, absolute suicide for a midnight hike.
"I've circled 20th three times," Caleb sighed, his jaw clenching. The honeymoon phase was officially over. We had entered the Parking Phase.
In San Francisco, circling for parking is the ultimate relationship pressure cooker. It’s a delicate dance of unspoken resentments. Do I offer to pay for the $40 garage, thereby emasculating his provider instincts? Do I get out and walk, abandoning him to the wolves of Valencia Street? Suddenly, I saw it. A sliver of darkness between a bus stop and a suspiciously placed dumpster.
"There!" I shrieked, tapping the glass. "Pull in! Pull in! Don't bump the driveway cut!"
Caleb whipped the wheel, executing a parallel park so aggressive and precise it was practically foreplay. But the post-coital parking bliss was short-lived. I stepped out onto the damp pavement to inspect the curb, praying for a lack of red or white paint.
In San Francisco, the parking signs read like a passive-aggressive novel written by a bureaucrat. I stared up at the metal pole, stacked with three separate aluminum warnings.
"Two Hour Parking, Monday through Friday," I read aloud to the cool night air. "Except Vehicles with 'W' Permit."
Caleb rolled down his window. "I'm a 'C' permit. Hayes Valley doesn't help us here. What else?"
"Well," I said, squinting at the middle sign. "It says No Parking 8 AM to 10 AM, first and third Monday of the month. Street Sweeping."
We stared at each other. The silence was deafening. I checked the calendar on my phone. Tomorrow was the first Monday of the month.
This was it. The precipice. The moment every San Francisco couple must face.
"I can set an alarm," Caleb offered, though his eyes darted away from mine. "I'll get up at 7:45, come down, and sit in the car until the sweeper passes."
I looked at him. We both knew he was lying. At 7:45 AM, enveloped in my organic linen duvet, the world outside would be a freezing, unforgiving gray. He wouldn't get up. He would hit snooze. He would get a $102 citation tucked beneath his windshield wiper. And then? The resentment would build. It would start with a parking ticket, and it would end with us silently splitting $9 artisanal toast, questioning every life choice that led us here.
In a city so obsessed with optimizing every second of the day, it's a miracle any of us have the bandwidth left for romance. We are all just endlessly circling the block, hoping to find a spot that won't cost us everything we have.
I looked at the pinkish-red curb. I looked at Caleb's exhausted, handsome face.
"Start the car," I said, slipping back into the leather passenger seat. "We're leaving it."
"Are you sure?" he asked, a mixture of relief and panic washing over his features.
"I am not letting our relationship die at the hands of a street sweeper named Gary," I declared.
We drove another ten minutes, finally ascending the steep, calf-burning incline of Dolores Heights, where the air is thinner and the street sweepers only come on Thursdays. We parked a mile and a half from my apartment.
As we locked the doors and began the long, freezing trek back down the hill in the dark, my boots pinching with every step, Caleb reached out and took my hand. It wasn't a fairy tale ending in a penthouse suite. But as we shivered together under the San Francisco streetlights, I realized something: maybe true love isn't finding the perfect spot right outside your door. Maybe true love is being willing to walk a mile in the freezing cold, just so you can sleep in together on a Monday morning.
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