Freakin’ Yuppies

The pursuit of the world's most bizarre dives takes a weird turn at San Mateo's Yuppie Bar.

“It’s my Friday,” says Amy the jovial bartender, a 60-ish woman with long gray-white hair. “I’ll have to start drinking soon.”

It’s Wednesday afternoon, and Game 2 of the World Series is about to start. There are boxes of cherry tomatoes on her bar, and before we order anything, we convince her to use them to make us something highly unpalatable. A little prodding, a little hesitant back-and-forth between friendly seeming strangers testing each other’s sincerity, and she’s making chilled Kahlua-and-tomato-juice shots for herself, me, and Wes Rowe, the proprietor of Wes Burger ‘N’ More.

“I’m going to taste it,” Amy says, pausing over whether to blend or muddle it. “I dare you, if you double-dare me.”

“I told you already,” Wes says, “I’ll drink one if you do. Salt the rim!”

Six months ago, he and I went on a multiday rampage in pursuit of San Francisco’s best burgers, and as we got to know one another, we learned that we share a passion for finding the world’s weirdest, most amazing dive bars. So we’ve driven to San Mateo to come to Yuppie Bar, a surprisingly large dive that’s hard by the Caltrain tracks and which he’d stumbled upon years before on a double-date with a friend and two girls from San Jose. It’s on the southern end of downtown, near Ramen Dojo and Ramen Parlor and across the street from Espetus Churrascaria (whose only other location is on Market and Franklin streets in San Francisco).

The sign outside says “YUPPIE” in a blocky, college jersey-looking typeface beneath the international symbol for a dive: a martini glass with an olive in it. It’s cash-only, with Jell-O shots at three for $5. Decked out for Halloween and the Giants alike — same color scheme, handily enough — it’s got bats and pumpkins hung from the dropped ceiling amid faux-stained glass light fixtures in the shape of bunches of fruit. The sign in the men’s room reads, “Please do not deposit cigarette butts in the urinal. It makes them soggy and hard to light.”

I’ve drunk life to the lees at a DIY Bloody Mary bar in Boise, Idaho, that had dozens of hot sauces, I’ve gotten kicked out of the Carousel Bar at the Hotel Monteleone in New Orleans on Mardi Gras for trying to pee before ordering a drink, and I’ve been robbed at gunpoint outside a bar in Buenos Aires. But I’d never had a tomato-and-Kahlua shot. It’s not good, but it isn’t gross, either.

“It’s contrasting flavors,” Wes says. “You got salty, you got savory, you got sweet. Squirt some lime in there.”

“That’s not as horrible as I thought it would be,” Amy says, laughing at our collective stupidity.

“How much grosser can we make it?” Wes asks, egging her on for round two.

We throw down a shot of Early Times and an IPA chaser in the meantime. Two stools down, a barfly named Flash who’s watching South Park warns us not to overdo it on our new idea.

“They might come back to haunt ya,” he says, encouraging Amy to try tomato-and-Bailey’s, a proposal she prudently swats down on grounds that that shit would curdle.

With a Facebook page that hasn’t been updated since a post bidding a bartender farewell in summer 2011 — which got one like, and a comment in Arabic script in late 2013 — this place is the epitome of don’t-give-a-fuck.

Its name sounds like a tech-savvy way to game Yelp to climb to the top of a hate-search. (Can you imagine a dude with a ponytail and contrast collar, and whose BMW convertible has a carphone, choosing “Yuppie Bar” from among Downtown San Mateo’s diverse offerings with a sigh of relief?)

And although Yuppie Bar’s most recent Yelp review is a one-star slam that included the criticism, “Bartenders drink quite openly and their friends also drink and seems like for free,” that certainly does not seem to be true. Wes and I pay for every drink, even though we’ve definitely made a new friend. He then plays Funkadelic’s album Maggot Brain on the jukebox in its entirety. Amy turns it down to hear LoCash sing the national anthem before the game starts, and we attempt another round of tomato-and-Kahlua with a woman named Maggie who inadvertently stole my seat, along with her husband, whose name I don’t catch. They’re skeptical. We can’t get a very drunk-sounding woman with a voice like that of Patty Mayonnaise or Yoga Jones from Orange in the New Black to try one, either, so we get her to try on my hat instead. By this time, there’s a lively, bar-wide discussion about Bootsy Collins’ career, and Amy knows all about Wes Burger ‘N’ More. She’s selling the uninitiated on its virtues, especially the Portabella Reuben and tater tots.

“I like your sign,” she says, looking at a pic on Maggie’s phone. “Very retro.”

“I don’t think I’m gonna go back to work tonight,” Wes says.

He texts a girl he knows. I fail at every attempt to properly quote the dialogue in Wayne’s World when Wayne encourages Garth to throw up on a girl because “if you blow chunks and she bolts, then it was never meant to be.”

Maggie’s husband tells us about a weird drink he encountered in Puerto Vallarta that has something to do with jellyfish. I press him on tomato-and-Kahlua. It’s like chum, I say, going for a tenuous fishing connection. He’s still a no. We spitball various names. The Amy-liminator. The Flaming Moe.

Then Wes hits on it.

“This is what it should be called: a Go Fuck Yourself shot,” he says. “‘Cause if you tell people what’s in it, they’re going to tell you to go fuck yourself before they drink that shot. You would have one of those now!”

“No,” Maggie’s husband says, “I wouldn’t.”

Yuppie Bar 709 South B St., San Mateo 650-343-8183, no website.

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