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?

In my decade living within this 49 square mile bubble, I’d only been to Olive once and I didn’t remember a whole lot about it. So I was excited when Ruggy suggested that we meet there on Monday night. I hadn’t had any adult beverages in nearly five weeks and since Ruggy is about to move to New York, it only seemed natural to break my sobriety with him at a bar of his choice. Olive was the natural pick since it’s one of his favorite spots in the city.

As always I arrived a little early, which was perfect because it gave me time to check out the scene a little bit. Scattered throughout the medium sized bar were the kind of patrons you don’t usually see in a stretch of the city known as much for its drugs and hookers as it is for its, well…drugs and hookers. The crowd was nicely groomed and hip looking, like you’d expect to see them in some cool new bar in SOMA and not in the heart of the Tenderloin. Something about the place reminded me of the San Francisco I moved into ten years prior, when the last wave of the tech bubble had finally receded and we stood staring at a city ready to redefine itself after the bust of yet another gold rush.

Downtempo loungey electronica came through the speakers while I took a seat at the bar and inspected the drink specials written largely on iPad-sized chalkboards that dotted the bar top. The bartender informed me that since it was Monday night, all house cocktails were only $5. Weeknights win again. 

A few minutes later Ruggy walked in and grabbed a stool next to me. We talked about his upcoming move, my new apartment, life, love and most importantly, what food we were gonna order. Olive has a solid and diverse food menu, and while the pizzas were  tempting we ended up ordering the fish tacos and garlic baked brie. I could eat that brie all day long. 

As our food arrived, there was thud behind us. I turned around to see two girls I was friendly with freshman year of college, one of whom had just knocked a salt shaker off the table and onto the ground. The thing about seeing people you knew fairly well a long time ago and not really at all now, is that in a way, they remind you of who you were back then. Kate and Jasmine were two such people, and the four of us talked about the funny directions that life had sent us, how the fried chicken at the Gold Club is supposed to be off the hook, and the fact that Olive was one of the first bars Jasmine ever went to when she moved into SF nine years before. The bar was proving to be more than just a charming oasis in the TL with attractive rotating art exhibits and a super friendly staff. That night it was a place where a few thirty somethings  measured their life experiences against their expectations and tried to figure out if and where they matched up. Kate was now married, Jasmine was finishing grad school, Ruggy was moving to New York and I was trying to figure out when I’d be able to get to the Gold Club to try that fried chicken. Well that and a few other important life decisions.

Nights like Monday can’t be planned, they only happen when you give yourself to the City and let her do with you what she wants. That said, I wouldn’t be surprised Olive played as much of a role in opening up the night as anything the four of us could’ve said or done. Maybe it was the baked brie.

Stuart Schuffman has been called "an Underground legend" by the SF Chronicle, "an SF cult hero" by the SF Bay Guardian, and "the chief of cheap" by Time Out New York. He is also the host for the IFC travel show Young, Broke & Beautiful. Follow him @BrokeAssStuart.