I looked at a pdf version, and realized I recognized the title from the big "pick up" craze from the time period (which included spawning movies like 40 Year Old Virgin). Is this what started that? My first thought was that this 'negging' thing seemed counterproductive, but then I thought about times when I have accidentally burned women with my particular sense of humour, and how it hasn't caused them to disassociate themselves with me. I also figured that it may be overthinking talking to people on the whole, but if somebody is so caught up in their head that they have trouble communicating, maybe this sort of strategizing is just what they need to make friends? Maybe somebody who seriously has trouble meeting new people could put it to good use, at least in terms of the first few "steps" the author posits.
Overall, it seems rather mean-spirited at first glance, but it isn't anywhere near nonconsensual or traumatizing for the woman. The manipulative aspect is inherent in self-help guides about persuasion. This book is also far more ethical than the version designed for heterosexual females, "The Rules", which includes a chapter called "Don't tell your therapist about The Rules". My favourite image reading this book is of guys wandering around bars calling people ugly in the hopes to score.
Also, I should note that I dress exactly the same way as the man on the left in MSH's photo. With variations which include a corduroy jacket, or a red scarf, or other accessories. One time I went to a club wearing a garish blue ocarina around my neck because somebody told me it was a fairly trashy place.