Say I see a pretty girl in a seduction-friendly (e.g. library) or -unfriendly (e.g. bus stop) environment. If I walk up to her out of the blue, smile nicely (/r/rateme told me I have a very nice smile) and say 'hi, we don't know each other and please excuse the directness of this question, but would it be possible to invite you for a cup of coffee sometime?', does a strategy like this have a chance of working? What are the factors that affect it in a positive/negative way?

Big thanks for all your opinions.