Is it okay to ask a woman out while she’s working?

I am curious about someone who works at a place I go fairly frequently. My first question is that I'm not sure if the curiosity has a romantic component or not and I want to know if it is bad policy to pursue her, even if I'm not sure I'd want to date her.

How do I approach women in bars?

I'm going on a road trip in a couple of days. I imagine we'll be hitting some bars, pubs, etc., could you give me some tips on how to approach women and make them interested?

How to approach an unapproachable woman?

I don't normally have issues with approaching women that I find attractive, but I have silently walked by the same gorgeous woman 3 times in the past month. Each time she maintained eye contact with me or smiled. I kicked myself the first time for not saying something, and then kicked myself harder the next two times, vowing never to do it again. Yesterday, I saw her. And didn't say anything. I've never been so paralyzed before. Advice?

Is she playing me?

While helping my buddy move, I decided to take a break and hit up the Starbucks around the corner. I order my coffee and sandwich and sat outside in the sun. I walked up to a table one seat away from an attractive girl. I said nothing as I ate my sandwich, but couldn't help but notice she was playing with her hair and looking my way. I finished my sandwich got up and walked inside.

I want her to ask me out!

I'm a 32 year old male looking for solid relationship. I'm pretty good looking I think, and I don't have a lot of trouble meeting women. In fact, I've dated a lot over the past couple of years. I've tried dating sites and being set up by well meaning friends, but nothing has really lasted longer than a couple of dates. I can't seem to meet a woman who is really my type, and to be honest, it's wearing me down a little! The part I find the hardest, no matter how often I do it, is getting up the nerve to ask. It's a little nerve wracking, putting myself out there every time. I'd love it if, for once, a woman approached me and did the hard work! What are my chances?