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

Talking to Strangers | Baby Step #1

At brunch the other week, my friend KP and I started talking about dating, as we always do. She told me about a friend of hers who had just moved to Chicago from San Francisco. "You know what's different about Chicago?" he said on a recent visit back. "When you go to bars there, you don't just talk to the people you came with."

That is so true. I remember one night when KP and I were out with a group of other single girl friends. We were going to meet boys. Our friend T., who has a longtime boyfriend, found a spot where we all could sit--on the kegs in a side room--and we all rebelled. No guy is ever going to talk to us back here! But we were looking at it at too micro a level. No guy was going to talk to us, yes, but not because we were hidden away. It's because we were in San Francisco.

It's not that people here are unfriendly, it's just that it's not a "talking to strangers" culture. It's a "I go out to have a good time with my friends, and, maybe, their friends" culture.

I realized what I needed to do: I needed to learn how to talk to strangers.

Here's the other insight about dating in San Francisco that I recently gleaned from a friend: no one's got game. "You go to New York, you go to L.A., and guys know how to ask for your number," she said. "Here, all the girls are all third-wave feminist about it. They try to be interesting." At first, I wanted to disagree. But after about five seconds, I knew she was right. I try to be interesting. I talk about New Yorker articles and how effed up Iceland's economy is. That's interesting and challenging and life-partnery. But it sure isn't sexy.

So I'm starting a whole new tactic with this blog. I realized that--like sports, like learning an instrument, like anything, really--if I want to improve, I need to work on my fundamentals. I used to have OK game. Now, I have no game. I need to get game. Talking to strangers is step 1.

Tonight, after a slog of a day at work, I decided to take a detour on my way home at my friend's bar. I went in, said hi, and immediately A., a fellow musician who I've met before, said, "Sit down, have a beer." So I did. We talked about music, remote islands, pirates, the East Coast (he's from Pennsylvania). It was fun. Then he got up to start playing the house piano. Mission accomplished.

I was about three-quarters done with my beer and thinking of heading out when J. sat down. Out of the corner of my eye, he seemed kind of cute. I saw he had a hardbound book. OK, I can do this, I thought. "What are you reading?" I finally asked. We started talking about language, linguistics, where he's lived, where he lived with his ex-wife, and where I've lived. And, also, his girlfriend and her two kids. After a while, I had to head out and he had to head out, so we introduced ourselves in that oddly comfortable yet still odd way that comes at the end of a long conversation.

As I hugged my friend goodbye, he said, "Did you get that guy's number?" I told him about the girlfriend and kids. But it wasn't about that. I was pretty excited about the basic, though boring, achievement of just talking to someone I've never talked to before.

Baby steps. Next up: remembering how to flirt.