It's most ideal for me to check things out after work. I work until 11pm, walk ten minutes east and I'm in the Gaslamp Quarter, the heart of downtown San Diego's social scene. San Diego is very casual. I work in a suit, so when I hit the bars, I tend to stand out quite a bit. Being all alone, even more so.
My first night on the town, I discovered that the Gaslamp is a loud concentrated section of bars and clubs. The busiest places charge at the door. Partly because I'm cheap, and also partly because I just know better, if a place charges at the door, it usually sucks inside. The cover charges here range from $5 to $20. I sought out the places that had no cover and found myself at a quiet Irish pub. Quiet compared to whatever else was around. Irish compared to whatever else was around.
I had no plan, so I just took a stool at the bar and people-watched. I think the bartender appreciated having someone dressed in a suit in his place. After maybe 10 minutes of just relaxing and observing a young woman decided to chat me up for some time. More focused on why someone would come out alone, in a suit, the conversation eventually grew a bit annoying. When she offered her number under the circumstances that I must call her, I was honest and declined.
I believe it's really tough for a lady to offer her number rather than have someone ask for it, so I felt a little bad. But in the end I guess it's a tiny confidence boost for me.
Two days later, I ventured out again after work in search of the Whistle Stop Bar. Two people at work recommended it for a fun atmosphere. Turns out it was a hipster haven. I left New York hoping to never see another goofy hipster again, and it turns out there are plenty of them here too.
Again, it's after work, so I'm in a suit, standing amidst a room of dirty hipsters. Like a sore thumb, I stuck out. The bartender was either too busy, or didn't wish to pay me any attention. So after five minutes of waiting, I took off for another spot down the street.
Fortunately it was not hipster headquarters. This bar was big, new, and they not only played awesome late 80's early 90's music, but they also played the music videos for the songs. The bartender was happy to serve her new patron who wasn't dressed like a bum. I got a Tanqueray&Tonic and just relaxed, watching an old Bobby Brown video. This place was cool.
I noticed, from the corner of my eye, a girl left her table of friends to come and order a beer at the corner of the bar. She got her beer and sat right there. Didn't return to her table. I must've looked her way. She asked me why I wasn't drinking beer. I probably told her that it's bad for you. I invited her to the seat next to me and we chatted for about twenty minutes about anything.
Anyone who knows me, knows that I don't chat about anything with anyone for twenty minutes.
I took her phone number. Called her two days later. We had lunch. I wasn't really into her after that. I think it's mutual.
Halloween Eve. Plenty of people are out in costume. Me, suit, again. I like the suit. I believe in the suit. Stand out. Look classy. My concierge gave me a list of rooftop bars through the city, but since she's an older lady, she would never venture out late at night to try them out. I figured I would check some out, since I'm going out anyway, and give her some feedback.
Still, I won't go anywhere with a cover charge. So I try the first one. No cover, but there's an enormous line. Just as bad as a cover charge. Bars here close at 2am, so why waste thirty minutes on a line? Next.
Another no-cover spot, no line either. A quick elevator trip to the rooftop. It felt a little TOO modern for me and I was really turned off by the fact that the bar had no seating. Being out alone is tough enough, but STANDING alone just seems unbearable. Anyhow, I was standing for 8 hours at work. Gimme a seat. Next.
Hard Rock Hotel has a rooftop bar, so I go to check that out. Before I get in the elevator, the hostess says "twenty dollars". I told her "good night".
There were plenty more bars on the list, but I was getting the feeling that a rooftop bar just wasn't going to do it for me. So I stopped at a little place called Cafe Sevilla. Tapas restaurant and bar. No cover. Live music. Two guitarists playing classic Spanish songs and throwing in a few modern rock verses to keep the crowd thinking.
Typical me, I sit at the bar and relax. I get my drink and turn to face the guitarists. They're frickin' amazing. Some couples are dancing in what little space the bar had. I'm sitting next to "Flo" from the Progressive Insurance commercials. With her is a 6'2" "Jail Bird". Jail Bird's sister is a 5'10" "Poker Dealer from Hell". Poker Dealer from Hell is quite attractive. She's being hovered over by two anxious older guys from either Italy or Spain. Jail Bird and Flo see me laughing at those guys and we talk a little bit, especially after I brought up Flo's very cool costume.
The two older guys start dancing with Poker Dealer from Hell and her sister Jail Bird. I tell Flo she looks like she's Anglo and she tells me she's half Irish, half French. Yatta yatta yatta. I'm just relaxing enjoying myself and being friendly. I look at Poker Dealer from Hell and laugh at how ridiculous these older guys are. She pulls my arm and forces me (not that I was really fighting) to dance with her. I was never good at dancing to Spanish music, but somehow I pulled it off well enough to convince a South American. Poker Dealer from Hell and Jail Bird are two very tall black girls. Turns out they're actually from Columbia. Jail Bird's accent seemed much thicker than Poker Dealer from Hell's. Regardless, we exchange numbers and I had an awesome time.
To recap: I didn't pay a cover charge. I didn't wait on a line. I didn't have to go to some trendy over-priced rooftop. Found a low-key off-beat place and it turned out to have the best atmosphere.
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