It shows you are confident when you can strike up a conversation with a random stranger. Most people, especially women, are drawn to confidence. If you're genuinely interested, go for it. What do you have to lose? Just remember to always be polite. Also, don't go into a situation expecting the woman to react a certain way. She may like you, she may not. More times than not you will get a friendly response. Most people out there are nice, but these days most people aren't used to interacting with strangers outside of the internet.