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?

I warned the PR people. I said, “You know what you’re getting into by inviting me to the Redwood Room don’t you?” I was referring to the high end call girls who famously meet clients there. As I can’t really afford to drink at the Redwood Room unless someone else is footing the bill, I hadn’t actually seen it for myself. But it’s an acknowledged part of San Francisco, and as someone who is drawn to writing about anything having to do with vice, I was intrigued to see the call girl-client ballet play out in front of me. 

Unfortunately call girls don’t come out at 7 pm. I learned that the hard way. There was no ballet to watch at that hour of the day, no confident women leading nervous men out of the bar by hand, no winks between friends that say “I know why that beauty is with that schlub.” So Cat and I sat on a couch, ordered some Moscow Mules, a cheese platter, and an incredible flatbread, and I learned all about the Redwood Room.

Situated on the ground floor of the very upscale Clift Hotel, the Redwood Room opened its doors in 1933 at the end of Prohibition. It’s beautiful. All the wood in the room is from the same 2,000 year old redwood tree and the inlay mural behind the bar depicts the riverbed where the tree was found. A number of years back, the entire place was renovated and while the original bar didn’t survive, it allowed Philippe Starck to do his magic, making it the sleek and sexy cocktail lounge that it is today.

As Cat told me this I fidgeted on the remarkably uncomfortable couch and nodded, pretending I knew who Philippe Starck was. I was pretty sure he wasn’t one of the Starks from Game of Thrones, but you never know in this town. I looked around the room hoping to see some action. Across the way, men in business suits were talking with a guy who looked like The Dude from The Big Lebowski. Considering the kinds of people who stay at the Clift, the dude who looked like The Dude was probably some famous artist who could buy and sell these men in business suits. I hoped so. Maybe the bums didn’t lose after all, Lebowski.  

People around us were soaking up their cocktails while drinking in the atmosphere. The digital displays that had until now been showing electric prints of Gustav Klimt paintings has switched to a number of moving portraits of men and women eyeball-fucking each other from across the room. Mostly it’s just their eyes that move, and the series of them supposedly depicts an Italian soap opera that has something to do with infidelity. And maybe that’s just it; when even the pieces of art want to sleep with each other, maybe your establishment is too sexy for its own good. 

The people watching at the Redwood Room was almost as good as the food and the cocktails. Women with giant shopping bags and equally large diamond rings gaggled and giggled over things I’ll probably never understand, while pretty waitresses showered us with excellent service. The wizards at the Redwood Room have beaten physics and have mastered lighting in a way to makes everyone, including me, look like a million bucks. I was just thinking that I could get used to this kind of thing: Good lighting, pretty people, expensive food and drinks, and lust-filled wall art, when Cat informed me I’d hit the limit of what she could legitimize the PR company picking up from our bill. So I went a few blocks over to the High Tide in the Tenderloin, a walk during which I was certain to see whatever action we were too early to witness at the Redwood Room.