For shorter-term relationships (not implying anything), I've found best success with flirting with women considerably more attractive than myself. I've asked a number of my more attractive girlfriends why they were with an ugly schlub like myself and I get two common answers: Personality/humor/laid-backness is one, and the other is that it seems that the best looking ladies either don't get approached, or don't get approached with anything better than tired old pickup lines.
I do agree with their findings on pickup lines though. Some friends and I spent a few weeks testing out different ones (in the name of science, naturally), and I had, by a large margin, the most success with "Hi, I'm Barry. Can I buy you a drink?" -- obviously varied if I'm not somewhere I can buy a drink from.
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