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Hello Db and welcome here
Honestly, i don't think there's a simple, black and white answer to your question. Sure, there are tons of sites, forums, books, even dvds on pick-up techniques, openers and a whole lot of other dating related mumbo-jumbo but based on my experience, walking down that path won't get you nowhere as social-dynamics is far more complex then a few funny lines, 2 seasons reruns of "Lie to me" (God i hate idiots thinking that show made them smarter in any way) or a Animal Planet documentary worthy, analysis of a a person behavior. To be explicit, when it comes to first contacts, you're in the fast lane as "instant gratification" are the magic words, and a pleasant smiles exchange can turn very fast into a "weirdo" tag on your forehead, but then again, that "weirdo" tag can be easily turned into attraction if you do this very very complicated thing called "speaking" Think about it this way DB : "What's the worst that could happen?" -> the conversation will lead nowhere and the two of you will be a bit more than strangers, which was the status you already had ? Don't worry, if she won't like you, she won't sound the village horn, gather all her females and other house pets, cows included, make a circle around you and follow you everywhere crying out loud and laughing "HE DARED !!!"
Think about it this way, number 2: every woman got picked on in her life, and in the age segment you're "hunting", she's probably getting it on a weekly basis, so her bag of "put you down" lines is way fuller than any bag of "pick-up" lines you could gather from the internet gurus. Also, she's really not looking for somebody to smack her down with some 3 hours long mind boggling conversations about the meaning of life seen through a cat's eyes, she's looking for a pleasant company and a fun time, one in which she can participate, actually talk not listen to you and look ugly at you when you shut up for a second. You can't deliver those two if you're constantly thinking what Mister_Sex_Guy_Ideal_Lover_of_the_Century_69 said you should say nor if you're planning your next funny routine like a washed up comedian begging for the audience's attention, simply because none of those 2 characters aren't the real you and the "pretending to be someone else to impress you" gets picked up really fast by most women.
Always keep in mind : What's the worst that could happen ? (and no, you won't be moo-moo'ed forever by the village cows)
"What you won't let die, won't let you live "