“A clever man, depending on his own ability, and observing carefully the ideas and thoughts of women, and removing the causes of their turning away from men, is generally successful with them.” – Kama Sutra, Part V, Chapter I, “On the Characteristics of Men and Women.
Well put, Kama Sutra; well put.
Love Systems’ president and presiding patriarch of the pickup artists Nick Savoy has noted that the number one move every untested man makes to turn her off is becoming the question guy: “Almost every man starts off by asking her where she’s from, where she went to school and so on. They’re looking for something they have in common with her, and they’re going to ask questions until they find it…[The problem is] she’s gotten these questions from random guys 1000 times before and is sick of it. Some women describe this as being like ‘being at an interview for a job I don’t even want.’”
His solution? Try the inverse. Rather than hammer away with questions, looking for something to latch onto, introduce yourself and let her find something she has in common with you. As a conscious exercise, be sure never to ask two questions in a row; Savoy suggests turning the question period into a guessing game by making statements and having her either confirm or deny them. This also opens up the ability to compliment her without it seeming unnatural.