Overcoming Bias has a post up about hypocritical flattery. RH might feel a little embarrassed getting a link from this universally beloved and highly influential blog, but his post is very interesting for what it implies about successful methods of flirting that men can use to pick up women. (See what I did there?)
Humans usually have a social norm against flattery. Yes we flatter each other, and often, but we usually flatter indirectly. So just how big of a fig leaf does it take to hide flattery? Consider item #1 from a post on “the seven techniques for ingratiation and influence that are most effective in moving up the corporate ladder without looking like a kiss-ass”:
Frame flattery as likely to make the boss uncomfortable. …one manager whom we interviewed noted that he commonly prefaces flattering remarks with such phrases as “I don’t want to embarrass you but. . . ,” or “I know you won’t want me to say this but. . . ,” or “You’re going to hate me for saying this but.” (more)
Note that this approach makes the praise seem no less glowing, and it offers little reason for observers to less suspect the praise was designed to gain favor. So how could flattery without this addition be unacceptable, yet flattery without this addition be acceptable?
This example suggests that the key social norm is that you should not encourage others to flatter you. While there is a weak norm against praising others to gain their favor, the stronger norm is against your explicitly rewarding others for praising you. So by directly claiming that someone is not encouraging you to praise them, you declare them innocent of violating the key social norm against encouraging flattery from others.
The key to effectively flattering your boss (or any higher status person who could be useful to you) is to clear him of suspicions that he may be encouraging the flattery. Similarly, the key to effectively flirting with a girl is to clear her of suspicions that she may be encouraging your come-on.
Girls know better, of course, that when they pretty up their faces and flaunt their bodies they are encouraging come-ons from men, and hopefully the right kinds of men. But that doesn’t mean they want to be reminded of that grimy little fact about their natures.
Girls are very sensitive to being thought easy or slutty (and with good psychosexual reason). Cloying flirtations that are tacitly sexual run the risk of triggering a girl’s anti-slut defense. There is also the quirk of the female hindbrain that she values, admires and, yes, feels more physical attraction for the man who does not make himself too readily available. Chicks dig chasing aloof alphas. A man’s conspicuously flirtatious proposition is more likely to lower his value than raise it.
Thus, the best flirting is a type of anti-flirting; flirting without directly signaling that you are flirting. Or without signaling that sex is on your mind.
A few examples:
“I don’t want you to get the wrong idea, but you look like someone who’d be cool to talk to.”
“I don’t consider myself in the market, but if I was, I’d say you’re kind of cute.”
“Why is it every time I just want to say something nice to a girl, like that your eyes are… unique, she thinks I want to have sex with her?”
“I hope you don’t think this is a come-on, but you have a certain grace about you.”
“Don’t be too embarrassed that I’m flirting with you right now. They’re just words.”
The idea behind these examples is that you disarm a woman’s inclination to pigeonhole you as a man angling for her sex. Once the outer labia force field is disarmed, a woman’s inner labia defenses are easily pried, and it’s a small matter to later “change your mind” about her.
Personally, I’m not a big fan of flattery flirting. There are better ways to flirt that don’t require the egregious use of compliments or greasy innuendo. But if you do like to go direct with your flirting, then framing your flattery like the examples above will improve the reactions you get from women. Especially very beautiful women who are used to “suffering” direct and insinuated solicitations from men.