Update from Monday's date with "Rocker Chick" (one of the skinny blondes from POF):
We had started talking Sunday afternoon on plentyoffish and decided Monday afternoon to meet that night. Plan was for drinks at a restaurant/brewhouse. I got there a few minutes early and waited outside. When I saw her walk up I thought "damn she's hot!"

The pics didn't really do her justice, very attractive girl.
We both apparently passed the "good looking enough / not clearly psycho" test, so we quickly decided to sit down for dinner instead of just drinks. Possibly reckless, but it was 8:00 and neither of us had eaten. Conversation was pretty good, although I had to steer things a little more than I'd prefer. Probably some first date nerves on both ends.
We talked about music quite a bit, since we both like seeing local bands. Not much common ground on the specific bands though. We did figure out that she saw my buddy's band one night. I was supposed to be there but had to go out of town. Otherwise there was a very good chance we could have met the old fashioned way, as I definitely would have approached her if I was there.
Overall it was a pretty good first date. Nothing spectacular. We were sitting across the table from one another, which really limited the flirtatious contact that can help move things along. Other potential issues...
1. She doesn't drink. This could be a problem. In general I'm more charming when I'm drinking, and
much more charming when she's drinking.
2. She's concerned that I'm too recently divorced. When I answered the "how long have you been divorced" question, she was very surprised and said something about how she shouldn't be here. Mostly joking but clearly some hesitation behind it.
3. There's some crazy there. I'm thinking it's an acceptable amount though. Enough to make her fun, but not so much that she'd flip out completely. I could be wrong though.
We both obviously have a lot of lines in the water, so I'm not sure if we'll get together again or not. My friend's band is playing Saturday, so I figured she'd be a good one to take to that. When I asked she said she has her son this weekend, otherwise she would. How my next two dates go will probably determine whether or not I ask her out again.