Something beautiful is happening in San Francisco's bar scene. The aggressive shot culture that once dominated late-night drinking has given way to something gentler, more intentional, and distinctly local: the cheeky.
These small, celebratory pours—typically an ounce of mezcal, amaro, or other spirits—have become the currency of cool across the city's best bars. But unlike shots meant for quick intoxication, cheekies are gestures of hospitality and connection.
"Think of the cheeky as a shot that grew up," explains Colleen Downey of Mission District's acclaimed Trick Dog. "It's less a vehicle for intoxication than a gesture of camaraderie."
The origins of the cheeky are debated—some trace it to Latin America (with "cheeky" an anglicized version of "chiquito"), while Future Bars CEO Brian Sheehy claims it started at Bourbon & Branch in 2006 when neighboring bartenders exchanged friendly nips of Fernet. Whatever its source, the phenomenon has become quintessentially San Francisco.
At Loló, a Jaliscan-Californian restaurant in the Mission, co-owner Leon Vazquez says they pour as many as 80 cheekies of mezcal on a busy night. At Casements, an Irish bar in the Inner Sunset, bartender Gillian Fitzgerald extends the practice to non-drinkers: "Anyone who's not drinking can still have a cheeky of ginger beer or soda water. It doesn't matter."
The cheeky comes with one unbreakable rule: it must be offered by staff. Customers who try to order one are effectively begging for free booze—a genuinely cheeky move.
For longtime observers of San Francisco's hospitality industry, the cheeky revolution reflects something deeper: a shift toward more mature, intentional drinking and a renewed emphasis on the connections that make great bars feel like community centers.
"It's a neat thing that could only start in San Francisco," Sheehy reflects. In a city known for invention and warmth, the cheeky has become the bartender's handshake—one small pour at a time.