Flirting and Chating.. When and Where is appropriate?

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Ok, so when you are at work, it is probably inappropriate to flirt with "Customers, and etc." as well as coworkers.. but then also, i feel that it is inappropriate to flirt with men on public transportation.. and walking down the street .. and etc.. i feel the most appropriate time is at a gathering of friends or something.men hesitate to approach women in public for the main reason that i dont want to inconvience them (well,so many "dog-like" personalities of men do so.. i imagine that the irritation would cause a metaphorical rush to even a friendly inquiry). So, i ask.. when and where is appropriate for flirting? :D