She is very nice and calls me by name when I go in, I know it's her job to be nice but I can't help but be interested in her.
I've only had one girlfriend in my life and I'm in my late 20s and I have no idea how to attract a woman, the only reason I had the one girlfriend for a few years is because we worked together for awhile and then she started showing interest in me. I am not shy and am very polite to her but I don't know how to leave customer mode and get her to see me as a potential date. Another problem is I know nothing about her, if she's single or even her age.
My question is mostly for women maybe even ones who have worked as a waitress, how would I go about getting some of this info from her and show interest in her without coming off as a creep or just another guy who hits on the pretty waitress? What would some of you suggest I could say to her that she would respond positively to?