Weekends are for amateurs. Weeknights are for pros. That's why each week Stuart Schuffman will be exploring a different San Francisco bar, giving you the lowdown on how and where to do your weeknight right. From the most creative cocktails to the best happy hours, Stuart's taking you along on his weeknight adventures into the heart of the City's nightlife. So, who wants a drink?

Live in San Francisco long enough and the phrase “This is a very small city” becomes something you say so often that it almost sounds like a mantra. It’s used to explain all the wonderful little coincidences in your life (like running into your best friend unexpectedly) as well as all the little disasters (like running into your ex with his or her new boo). What we don’t often realize though is that, as The City continues to hemorrhage residents, the East Bay is also quickly becoming a very small place. I learned this particular lesson a few months ago while on a date at The Alley. 

My date and I had arrived already a bit sauced from the combination of Café Van Kleef’s famous greyhounds and the walking potion (whiskey) we’d drank while ambling towards The Alley. Marching through the door, high on booze and pheromones, I saw a friend I’d gone to college with who, in recent years, had become more of a “friend.” You know the kind of friend I mean, the kind who you date casually for a little bit and then, when that slows down, you see every few months, usually spending the night together. Being single in your late 20s and early 30s means having blurry definitions of words like “dating” and “friendship.” My friend, also on a date, was sitting around the piano waiting for her turn to croon. I didn’t know she could sing.  

I’d been to The Alley a few years back when my buddy Sayre Piotrkowski had taken me on a drinking tour of Oakland in order to extol The Town’s many virtues. I’d fallen in love with the place because it truly was the perfect, old-school dive. With dim lighting and little diner booths littered about, one can easily find a corner to disappear into. The bar’s interior isn’t just covered in business cards, it’s enveloped by them; fifty or sixty thousand of the bastards are stapled to the walls. It’s like that cat from a Beautiful Mind went ape shit in there. Apparently amongst the many are business cards from Jerry Brown, Gregg Allman, and of course Broke-Ass Stuart. Seeing as the cards are a fire hazard, the bar sprays them down with fire retardant. But there’s more to The Alley than just retarding fires–there is the legendary Rod Dibble, the man who has been playing the piano there, nightly, since 1960 (he's rumored to know more than 4,000 songs by heart). I’m pretty sure the only vacations he’s ever taken are the weeks in bed following each of his three heart attacks. His most recent one was at the end of last year, and he was back behind the ebony and ivory three weeks later. There should be memes and stickers and street art of Rod Dibble with a speech bubble saying “Your work ethic ain’t shit,” while pointing at the viewer. 

Part of having “friends” is that at the root of your relationship, you should really be friends. This means not being weird or awkward when you run into each other unexpectedly with other people. And we weren’t. After her song my friend came over and we met each other’s dates and chatted a little bit before they took off. These are the kinds of things you have to expect when being single in a place like the Bay Area. And it’s also the kind of thing you have to expect when going to The Alley. A place that cool only attracts that best kind of people, the kind of people that can become any variation of the word "friend."