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I dont like the word "neg". There's a few definitions that I dont like using that this community uses way too often. This being one of them.
Back-handed compliments, on the other hand, can be useful if your joking around with her. Tell her how much you love going out with girls with a little extra meat on their bones and rub her tummy. Things like that in a joking manner are amazing. It makes her feel less secure and she cant really get mad at you for saying it. Saying things like this will get those little gears grinding and if she really cares what you think of her, she'll fight tooth and nail to make herself more attractive to you.
Something simple as that is great. Dont be afraid to speak your mind but dont be insulting. Bust her balls on that shitty purse she's wielding around or call to attention those satellites hanging off of her ears. All the while keep the biggest, goofiest smile on your face. That isn't being an asshole or anything, your just playful. This is lethal in small doses, dont let this be the only thing coming out of your mouth. After busting her balls on it, tell her that she looks fabulous anyway. You'll love her no matter how horrific that purse is!
Negs do work best when a woman feels she is at her attractive peak. When she's out on the town all dolled up and looking like a million bucks. When she's sweaty and smelling like shit she'll know it and calling her attention on it will basically just be an insult. Talk about the actual gym, how long you've been going there, what you do there, why do you like it? Things to that nature. Trust me, when you talk with a woman long enough, she'll give her own material for you to neg her with so dont focus on that so much and just get IN there first.
What you're talking about is "teasing" and "flirting."
I am totally for those things. Busting on a girl when she does/says something retarded or likes something nerdy or anything like that, in a playful way, is the essence of creating fun sexual tension with a girl, and showing you have a strong frame and are not going around just agreeing with her and trying to build rapport.
However, a NEG is defined as a backhanded compliment, as in "nice nails, are they real?" To me, this is a totally pointless thing to say. Coming from a classic rAFC who's probably quite socially uncalibrated, it will sound either purposely insulting, or like the guy is socially retarded and slipped up and was trying to say a compliment, but is nervous and accidentally insulted her, at which point she'll be like "what the hell did you just say?" No wonder guys on here complain about being "shit tested" all the time!
Furthermore, the basis of teasing and flirting is generating a playful vibe with her that she enjoys, and shows that you understand how to communicate with women and is subcommunicating that you're into her, but you're not a pushover and she's gonna have to stay on her toes with you.
The basis of the neg is the assumption that the woman is higher value that you, and you have to "knock her down a peg" and make her second-guess herself. It's also a "false disqualifier" i.e. a purposeful LIE to make her think that you're not actually interested in her. Again, WHY? Why not assume you're high value, and why not just be totally up front about the fact you think she's hot? Wouldn't that just be easier?