Before I cleaned up my act, the most time I spent in the Tenderloin was walking into, and stumbling out of, Aunt Charlie’s Lounge, the neighborhood’s drag-themed dive bar. Although I’ve survived a couple of physical altercations on these infamously colorful streets, living here has also been a bit of a pipe dream. The gorgeous historic apartment buildings, the unrestrained joie de vivre, close proximity to Union Square, public transit at a whim—it all comes together for a highly intoxicating siren song. But now, the TL is cleaning up its act, too. Apparently, others see my vision, and they’re moving in fast. Does San Francisco need another Divisa-lencia?

Supposedly named for the prime cuts of beef that butchers supplied to tony Union Square hotels back in the 1920s, the Tenderloin—loosely bordered by Market, Polk, Mason, and Geary—is casting its magically gritty spell upon Silicon Valley techbots and top chefs alike. Claiming turf are Daniel Patterson (Coi) and Roy Choi, who will open their healthful take on fast food, called Loco’l, at the rough-and-rougher intersection of Turk and Taylor; and Spruce’s Mark Sullivan, who will cut the ribbon on his two-level concept bar Saratoga, at Larkin and Post, this fall. As the saying goes, build it and they will come: Wide-eyed millennials and tech ilk just love to mingle over $15 cocktails on the wrong side of the tracks.

"Sure, it’s a tough neighborhood, but there’s something exciting brewing around here,” says Sullivan, noting the area’s rapid transformation. At Huxley, the new 25-seat bistro where I savor an otherworldly short rib potpie, I could hardly feign anger at the shiny new Range Rover parked outside, or at the hulking Google bus as it lumbered up the sketchy, dimly lit street. As much as I love the grittiness of this place, where urban chic converges with sheer terror, it’s also charmingly scrappy and fearless, and has existed in a state of peril for far too long. After all, until recently, the TL has been best known for its—how can I put this delicately?—unfortunate public display of odoriferous human waste. This neighborhood deserves to thrive.

Alas, a burgeoning zip code needs more than a few James Beard Award–worthy menus to spring to life. The last thing this city needs is another Mission District, which some longtime residents see as a hoity-toity food court for Airbnb guests and wannabe urbanites. Can the Tenderloin stave off this kind of overzealous gentrification? Not if the proven formula of longstanding blight plus new, too-legit culture holds true.

Opened last fall in the historic home of Original Joe’s, PianoFight is fine-tuning the arts in the neighborhood. With two playhouses, three rehearsal spaces, and  a restaurant and cocktail bar tricked out with a cabaret stage, PianoFight is "a one-stop shop for theater, comedy, variety, music, and film," says cofounder Rob Ready. Meanwhile, CounterPulse, the highly respected incubator for emerging artists, is moving into a former strip joint on Turk, joining other mainstay culture-tastic establishments, including Exit Theater and the Center for New Music. The 950 Center for Arts and Education, a massive multi-disciplinary arts building, will begin construction in 2016. Over the next couple years, the area will be home to well over a dozen stages.

The Tenderloin community itself, an exotic populace of down-and-outs and creative denizens alike, is perhaps playing the biggest role in its upswing. According to District 6 supervisor Jane Kim, “It’s not just an influx of tech workers and wealthy VCs changing the neighborhood….The community has taken on the same issues [like pedestrian safety and street lights] as, say, my more affluent constituents in South Beach.” At the behest of longtime TL residents, Kim helped clean up the first block of Turk, one of the city’s most notorious hubs for narcotics, by placing a ban on parking that curbed drug dealing. “There is no other neighborhood in SF with this strong sense of community,” she says.

But if you really want to know all about the TL, Del Seymour, founder of Tenderloin Walking Tours and the nabe’s unofficial mayor, has lived on these neighborhood’s streets for 30 years as an addict, as a taxi driver, and as a volunteer at the local nonprofits. His clients include Twitter and Spotify, who hire Seymour to show their staffers the good, the bad, and the ugly of their new surrounds.

During our three-hour trek around the ’hood, we checked out Boeddeker Park, which underwent a drastic renovation last year; visited the Tenderloin National Forest, a former needle-littered wasteland that’s been transformed into lovely green space; and we even chatted with some of the SFPD, who bragged about making the district safer.

But then, we were faced with a fully sobering moment when we hit Saint
Boniface Catholic Church, a beautiful Romanesque Revival sanctuary on Golden Gate Avenue that was rebuilt after the 1906 quake. On this particularly sunny Wednesday afternoon, pew after pew of homeless men and women slept head-to-foot in complete silence. That I had spent time selecting a head-to-toe outfit from Rag & Bone, a brand known for its urban cool factor, suddenly seemed, in this sardine can of a church, distasteful.

Even on the verge of a stylish resurrection, humanity continues to warm the cold, hard reality here. But before I could hum the faintest “kumbaya,” gunshots rang out—a half dozen, to be exact. Inside the corner market at Turk and Leavenworth, a mere block from where we stood, two men were shot in broad daylight. Police swarmed. The street was systematically blocked off. Crowds formed. It’s another good reason not to give my 30-day notice at my SoMa apartment. At least, not yet.

This article appeared in the March 2015 issue of 7x7 Magazine.