100 Emails, 20 Dates An SF girl's systematic quest to end her singlehood

Mastering the art of self-sabotage

This month, I was looking forward to my band's regular gig even more than usual. See, last month, my bandmate, the hot surfer dude (who, it turns out, graduated college 10 years after I did), and I closed out the bar, which is always a fun thing to do on a Monday night. R., the surfer, is a regular there, so I was hoping I'd get to flirt with him again. I don't really think that we're a good fit, dating-wise, but ooh boy, I sure want to kiss him.

He was there, sitting at the bar with another surfer type. I saw him as I went to pour myself a beer, but he wasn't looking up. On my way back, I caught his eye. "Hey, N.," he said. "Hey, Matt," I replied, and walked backstage.

I talked to him for a second at the set break, but he was gone by the time we finished. "That was nice of R. to come. Did he leave already?" my bandmate asked.

"Oh no!!!" I said, doubling over from embarrassment. My friends asked what I was talking about. "R.!! I called him Matt!"

"You can fix that," the bartender said. "Just say Matt was your first boyfriend. He'll be bummed, though."

"Why?"

"He really enjoyed talking with you last month," he told me. "He really enjoyed talking with you."

I don't know if it's bad luck or karma or something in the universe wanting me to stay single, but during the occasional periods when I have good boy luck, it's immediately followed by some stupendous act of self-sabotage. You know, like calling a really nice guy who I genuinely enjoy hanging out with and definitely want to smooch by the wrong name.

Even worse, I did it again. My friend K. invited me to see her boyfriend, D., and a couple of other friends spin. She sent me the invitation, and I said, "Oh, I didn't know you knew B." It turns out she and D. were thinking about trying to fix me and B. up. It turns out I had a small crush on B. when I met him briefly about ten years ago. He, really, is exactly the kind of guy I should be dating.

The night of the show, my friend J. and I went out for rum drinks at a pirate-themed bar. After two exceedingly stiff drinks, I was feeling pretty good: buzzed enough to dance, sober enough to not make too much of a fool of myself. We went to the show, we ordered two more drinks, J. left early, and as I walked back in, wondering whether to stay or go, I passed B., who K. had introduced me to earlier.

"Hey," I said, touching his arm to get his attention, which I thought was a smooth move. "Have you seen K. and D.?"

"They're all the way up in the front," he said.

"Hmmm. My friend just left, and I'm trying to decide if I want to make my way all the way up there," I said. And then we started talking. It was one of those fun first conversations when there are no awkward pauses and you learn so much about each other in a short amount of time.

Maybe it wasn't such a short amount of time. At one point, D. came up and told B. that it was his turn to spin, but D. could do the set if he wanted. B. said sure.

It was loud. So loud that there was no chance of interrupting each other because when one of us would start speaking, we'd have to move our mouth to the other person's ear in that pleasantly forced-intimate way. We talked about country music and our shared admiration of the Nashville hit machine. There aren't many guys in San Francisco like that.

It ended when he had to go to the bathroom and I had to get water. After I found K. and the glow of the conversation wore off, I realized something. I had been cursing like a sailor the entire time. Eff! <=(This is how I usually curse.)

It feels like it's been so long since I've met guys who I like and who seem potentially interested in me. And it's so frustrating that I'm so woefully out of practice that I keep shooting myself in the foot instead of making a decent first impression. Argh.