When I told friends in San Francisco my husband and I were coming to visit and staying in the Tenderloin district, they gasped. What about perfectly good hotels near Union Square, Fisherman’s Wharf, the Ferry Building, Golden Gate Park, and other places unique to the City by the Bay?

For one thing, we like to discover non-touristy sectors of places we visit, places with good bars for playing gin rummy all afternoon. We have a favorite Irish pub in Paris, a saloon in Bruges with a view of the Belfry from which Brendan Gleeson jumped to his death in the movie “In Bruges,” and a Tudor establishment we discovered on this trip, in Carmel.

(Note to other gin players: in our excursions, only the Buena Vista Cafe in San Francisco and La Tuna in San Antonio have shut down our shuffling. Yeah, like we’d gamble.)

We do acknowledge the Tenderloin isn’t anyone’s idea of a travel destination, what with its reputation for crime, drugs, and crazies. Wired Magazine described it in its February issue as “a sprawl of code-red despair,” where untreated mental illness and open shooting up on the sidewalks is rampant. But we don’t mind stepping over sleeping humans on sidewalks and learning about our erudite hostesses’ friendship with prostitutes, who buy her dogs treats. Plus, the Tenderloin’s location is ideal, between Nob Hill, Union Square, Market Street, and Van Ness.

The hip bar/restaurant that my husband, friend, and I dined at in Saratoga.
The hip bar/restaurant that my husband, friend, and I dined at in Saratoga. Credit: Nancy Cook-Monroe for the San Antonio Report

The personal despair I experienced in the guest room of our friend’s antiques-and-art-filled 20th floor condominium could hardly be described as “code-red;” code-beige set in when my prescription sunglasses went missing. Surely they were amid the objets d’art scattered liberally through her home, all so precious we joked they had been curated by the McNay Art Museum.

We retraced our steps to Saratoga, a hip restaurant and bar where my husband, our hostess, architect Janie Smith, and I had consumed $18 hamburgers and $16 stems of wine the night before. A guy came out of the kitchen and took my number in case my glasses were found. Despite what we’d heard about the Tenderloin, everyone had been really mellow so far.

A half block down Geary Street, we stood in line at Jane, a casual place specializing in sandwiches on freshly baked breads and salads you can’t make at home. Halfway through ordering a Salade Niçoise, I was interrupted by sudden commotion: right next to me, a tall black man screaming gibberish grabbed the metal tip jar, upturned the container and nabbed the bills as coins clattered to the floor. Diners rushed to pick them up for the servers.

“That’s so not cool,” the girl behind the cash register said to the man, the smile fallen from her face.

“Just go, get out of here,” a bearded server urged him.

Jane, where we had lunch and witnessed a man steal from the tip jar.
Jane, where we had lunch and witnessed a man steal from the tip jar. Credit: Nancy Cook-Monroe for the San Antonio Report

The robber ranted some more at the door and was gone. The young woman went on with my order.

“We thought he was gone from the neighborhood, but I guess he’s back,” she said.

Against this social backdrop, the Tenderloin has been experiencing an influx of money and ideas as Wired, Twitter, Zendesk and other tech companies have opened offices in and near the Tenderloin with the help of City incentives. Their young, well-paid employees are changing the dynamic of the Tenderloin, taking advantage of the last affordable rents in San Francisco.

Developers are having a field day. A raunchy joint called Heroin Hotel is getting $4,000 a month in rent for slickly renovated one-bedrooms. The first floor of the building had been vacant for 15 years when our friend Janie and her co-architect were hired to space-plan for a new restaurant and wine bar.

“Water was dripping down the walls and you had to use a ladder to get to the mezzanine level,” she said. “It was freaky, with schizophrenic graffiti, blood, stuff like that.”

Now you can barely get in to its pricey restaurant, she said, though the wine bar isn’t doing as well as planned. The owner is thinking of turning it into a more lucrative business.

Smith, a graduate of UT Austin and sister of San Antonian Betty Boston, has worked as an architect in San Francisco since 1995. Though warned about the Tenderloin’s rough, drug-dealing ways, she wasn’t deterred – she grew up in the rough and tumble of Amarillo and has lived and worked in New York City. She could see herself living in The Hamilton Condominiums in the Tenderloin where she had visited a friend. The former hotel/apartment building opened in 1930 and served as a home away from home for luminaries such as Lauren Bacall and Florence Henderson because of its elegance and proximity to San Francisco’s Theater District. The penthouse, a floor up from Janie’s two-bedroom, two-bath unit, is on the market for $3.95 million.

“They said this place is sketchy, but it doesn’t hold a candle to New York,” Smith said. “Yes, there are shootings, but it’s because drug dealers from Oakland come into the Tenderloin and set up shop. There’s worse crime in the Mission area [of San Francisco].”

When street people yell at her for no reason, she yells back.

“It’s really rather humorous around here,” she said. “You’ll get these people in outfits like Santa Claus hats in summer and Hawaiian shirts and leis. [They’re] really pretty tame.”

We saw Dianne Reeves in concert at the San Francisco Jazz Center.
We saw Dianne Reeves in concert at the San Francisco Jazz Center. Credit: Nancy Cook-Monroe for the San Antonio Report

As we walked from a concert by Dianne Reeves at the San Francisco Jazz Center to Janie’s building a mile away, we felt more appreciation for O’Farrell Street’s architecture than fear of attack.

“And the thing is, I’m like four blocks from Union Square [the retail heart of San Francisco with Saks, Nordstrom, Neiman Marcus, Apple, and Nike],” Smith said. “It’s never going to get totally gentrified because there still are so many social services here. But in the last two years, you can see some actual change.”

As similar neighborhood dynamics change in San Antonio, especially near downtown, the Tenderloin won’t totally transform into a high rent district in the foreseeable future because so many social service agencies feed and otherwise serve the physical, mental, and housing needs of the poor. According to Wired, the new techies in the neighborhood want to be involved in making the neighborhood safer and healthier, and are volunteering by the hundreds.

The Tenderloin may not near the top of your vacation list, but it certainly gives a richer understanding of San Francisco than riding cable cars and ferrying to Tiburon. And if you lose your sunglasses, they’ll catch up with you eventually. After we traced them to the floor of our Uber driver’s car, the driver delivered them, despite rain and wind, to our curb.

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Nancy Cook-Monroe

Nancy Cook-Monroe is a local freelance writer and public relations consultant. She has written about San Antonio arts and civic scenes since she could hold a pencil.