Sometimes when you least expect it.
I was heading west on Drake yesterday and decided to turn onto Archer to turn around. I wasn't looking at the time. I was just turning around to head back towards Knight. As I'm sitting at the stop sign/light to turn back onto Drake, a woman with an umbrella runs accross the street, closes her umbrella, and comes over to the passenger side of the car. Since she suprised me a bit, I more or less ignored her by pulling forward a bit to check traffic, then driving on.
Since I wasn't actually looking at the time, I had no idea of my surroundings, whether anyone was coming up behind me etc. So I didn't go for it. I took a long loop around a couple of blocks to anc came back around Archer a few minutes later, and she was gone.
White, blondish brown haie, slender, decently dressed, maybe late 30's or early 40's (hard to tell). I wouldn't have guessed she was woeking. If I see her again, I'll probably check her out.