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Women are not special little snowflakes in either the vaginas they possess or the insecurities which burden them. Women mostly share the same self-doubts: “I’m fat”, “I’m past my prime”, “He doesn’t appreciate me for my mind”, “He’s going to use me”, “OMG cankles!”, “My boobs are small/saggy/veiny/covered by an acre of areola”, “I hope guys can see how smart — SMRT smart! — I am”, “I hope he doesn’t think I’m a slut”, “She’s wearing the same shirt as me! Panic at the disco!”, etc etc.
You mission, should you refuse to be weighed down by useless pangs of guilt, is to make a woman’s insecurities your ally in the pursuit of closing the deal. You want to drive a wedge between her and her self-confidence. The reason is elementary: Women wish to date up. So a man can either raise his own status to appeal to the girl he is trying to pick up (see: Game, medical school), or he can lower the girl’s status so his status seems higher in comparison (see: Game, Skittles Man). He can also do both, but this might be overkill on women who are less than an 8. The last time I exercised both options on the same woman, it was with regular reader and bean diddler Sara, and you all can see the results of that in the comments.
Women are the gatekeepers to sex, but what exactly is the gate? It’s her self-perceived status relative to yours. Or, her beauty. Quite simply, if a woman perceives she is more beautiful than the kind of woman you can be expected to snag, she will give you a harder time than she would to a higher value man who looked and acted like the sort of man used to dating women of her beauty caliber. This dynamic also works with status metrics like educational attainment, because women project their desires onto men and assume men will up- or downgrade them on things that are important to women. We know better, of course.
Men have two intrinsic playing field advantages in the sexual marketplace. One, men have a longer window of sexual desirability. A typical 35 year old man has better prospects than a typical 35 year old woman. He won’t need to settle as far down the mate ladder as she will. Two, men can better withstand blows to the ego. We are designed to take a licking and keep on ticking, as we are, barring rare exceptions, the initiators of courtship. If you want to bang hotter women than you are accustomed to, you must leverage both of these advantages to the maximum.
Knowing this, you can easily improve your odds with any woman by subtly exposing her insecurities using the implements of psychological mindfucking. The trick is to avoid direct assault on her soft underbelly. You don’t tell a girl “I like your low rider jeans, but aren’t you worried that it accentuates your muffin top?” No, you need to breach her defense perimeter indirectly, like a Trojan horse:
“I’m sort of an exercise buff, so I appreciate a woman who feels the same way about keeping fit.”
Any woman with fat issues will hear this: “Does he think I’m not into keeping fit? Are my belly rolls undulating??”
More examples of the art of exposing female insecurities:
Use on a girl who looks like she might be self-conscious about her boobs: “Yeah, fake boobs are weird. If only women knew that most men prefer real, firm, round boobs.”
Use on girls pushing up against 30: “I think younger women are overrated. Sure, they have great figures and are spontaneous and always up for fun, but their lack of… maturity… can get tiresome after a while.”
Use on girls who have a slutty past (thanks to me, you’ll be able to tell) and are worried about being pigeonholed as a one night… hole: “Most guys are too judgmental about a woman’s life choices. I don’t believe in that. Only weak people feel a need to live according to other people’s expectations.” (Irony intended.)
Use on girls who are insecure about their smarts: “I just finished reading Joyce, but I’m not going to bother you with that. It’s a little high brow.”
Use on girls who are insecure about being perceived as high maintenance: “You like playing frisbee? Funny, I never would have taken you for the down to earth type.”
Use on girls who have bad fashion sense and worry about it (*every* girl worries about how she dresses): “I think it’s refreshing that you’re secure enough to wear flip-flops without irony. Not every girl cares about keeping up with the latest trends.”
Note for the haters: If my experience is any guide, women of high self esteem will fold like cheap lawn chairs to ego-evisceration game even quicker than putatively low self esteem women. Especially the grad school and lawyer chicks.