Approaching a new woman every day for a month, Day 12:
I tried something new: I decided to chat up a woman who was working, but not as a waitress or any other kind of service industry person. There was a cute little East Indian girl who was waiting with me as the parking meter was getting fixed by my work. I decided to chat her up because although she was supervising a local construction site and wearing a hard hat, she was also wearing a sexy skirt suit underneath her orange fluorescent vest that caught my attention.
She didn't realize that the meter (It's a special, advanced meter) didn't take dollars. Only cards and coins. I told her that I'd help her out if she needed it by paying her parking fee, but only if she agreed to pay me back with a coffee at the nearby cafe with the wad of cash she had on her. It was risky, but she was able to leave work as she pleased until some specific task was being worked on by the nearby workers, so it came up seven for me on this roll.
We chatted about work, school, etc during our visit. She's from the bay area and shared my love of science, football, and classic movies. I got a kiss at the end of our visit. Yow! Feels more and more natural to approach, but definitely wasn't ready for that! It's something that I could definitely get used to, though.
Oh, and I got her number.