My friends and I discovered a paradox of dating/picking up long ago, which I have discussed before slightly differently: essentially, humans have an ironic and disastrous habit of assuming the people they’re more attracted to aren’t attracted to them.
Let’s take a moment and dissect that. The people you think are hottest, the people that you reeeeally think you might click with, the people that you really fucking want are the ones who you’re most likely to think, “Aw, s/he’s just not that into me.” I’ve had many conversations with people where they readily admitted that they couldn’t tell someone was interested in them because of their own interest; behaviors that appeared flirtatious from someone they were not interested in immediately became ambiguous or neutral because they wanted that person.
WHY?
Why automatically assume that someone is not interested in you if you’re interested in them? It causes a disastrous cycle of dating failure; it’s spectacularly self-defeating in three crucial ways.
The first is that whoever the object of your attraction (OYA) may be, regardless of gender, they are less likely to be attracted to you if you believe that they’re not attracted to you. Don’t believe me? True story. They did an experiment where they didn’t let some poor guys bathe for 48 hours. Then at the end of it, they let some of the guys put on some scented body spray and some of them unscented deodorant, asked them to rate their feelings of confidence and then took the guys’ pictures and had them make videos. The guys who were scented rated their self-confidence higher than the unscented guys. Now here’s the kicker: they showed the pictures and videos to a bunch of women (who had no idea what the premise of the experiment was), and the chicks thought the guys who had on the scented body spray were hotter than the guys who didn’t. Now, unless women have developed some magical method of smelling men through photographs, the logical conclusion from this weird experiment is that guys are genuinely more physically attractive to women when they feel more attractive and confident (someone should try replicating this experiment with women). Which means that if you walk up to someone you’re attracted to, convinced that they aren’t into you, the chances that they’ll be into you are probably substantially lower than if you walk up to them, reasonably certain that they will be into you (overconfidence probably goes too far in the other direction).
The second problem with the conviction that the OYA isn’t into you is that you’re less likely to notice when they’re flirting with you, trying to make moves, or showing interest. Believing that they’re uninterested, you hesitate to interpret anything shy of, “Can we please fuck now?” as actual interest. (And I’ve even heard the insecurity extend past that point too! [Eeyore voice] “Well, she wanted me for sexxxx, but I doubt she wants to actually go out with meeeee”). If you get into a situation where both people are like this, then you have a fantastic recipe for a hookup or a relationship that is just never going to happen.
By now you should be able to see what the third problem is: if you continually “fail” to pick people up—because they’re genuinely less attracted to you because you think you’re unattractive, compounded by your failure to notice their cues of interest—then you end up “confirming” your own belief that you’re “not that hot.” Every time you fail to pick up someone you’re interested in, you become that much more insecure the next time you try… and less attractive to potential partners… and so the cycle of what we nicknamed “the self-defeating flirtation” goes.
But as obnoxious as this spiral of learned helplessness is, the thing I hate the most about the self-defeating flirtation is that it means that people often end up partnering with people that they’re less attracted to. If you’re terrified to approach the people you’re reeeeeally attracted to, and either don’t approach them at all or do so awkwardly, but more confidently approach people that you’re merely attracted to, you’re more likely to catch the people you’re merely attracted to than the people you’re really attracted to. And what a fucking waste. Go fuck the people you reeeeeally want!
“But how do I break the cycle?”
I’d be lying if I pretended like there was some easy way to just suddenly say to yourself, “I’m reasonably attractive. I might even be hot. There is a better than 50% chance that Person X that I am interested in wants me.” Me and my best friend realized that this cycle existed, and then pinky promised each other that we would try to always believe that people we wanted most found us desirable; in our cases, the pinky promise and Aphrodite worship worked. For some people, just being aware that they’re shooting themselves in the foot helps them try to change their thought processes and behaviors. If you genuinely, deeply believe that you’re unattractive, I don’t think any blog post will be enough to change your attitudes or behaviors on its own; that type of change requires something deep and powerful. But I feel like the majority of people that I know are insecure about how attractive they are in ways that are more changeable: the sort-of casual, everyday belief that one “just isn’t hot enough” has a hope of being overcome through practice, application, and the support of one’s friends.
Personally, I just find the reminder that the person is more likely to say “yes” if I believe they will to be a pretty damned good incentive.
Slut, Ph.D. 
There are things you can do to feel more confident even if you are as severely neurotic and insecure as I am. For example, in my case, I feel substantially more confident when someone is at my eye level. Since I’m really short, that means encouraging guys to sit down, but it genuinely does help. It’s a shallow thing, but you’re trying to trick your own brain into thinking you’re not intimidated, so doing an end-run around your own cleverness is kind of the idea.
I am so happy you have finally created a site with all your writings. I have always enjoyed your work, its like giving your brain an erection. The lack of intellectual discourse on sex is disappointing, and it takes people with courage. Stigma is a powerful motivator, especially sexuality in the USA, and I am pleased you are not intimidated. Please continue with this, people ARE affected by it for the better.
In regards to your topic, many great points. I think men have a different experience than women in regards to this. I am going to make up a statistic, and guess that women are approached far more by men than men are by women. I would argue that self confidence displayed in body posture has little to do with this. At the risk of sounding like a tool, I consider myself to be objectively attractive physically in bone structure, etc- I sound vain and egotistical already, so I’ll continue. I am never approached by women, but my women friends, even unconfident ones, admit to being approached by men. I have never heard one of my male friends say this. Because women are consistently approached by guys, the likelihood of them saying yes is about as likely as a customer in my telemarketing days saying yes to a subscription of magazines. I guess my point is that while woman may have a 50 percent of success, men probably have a 5-10 percent chance of a second date asking out a stranger.
This is fantastic, and really hit home for me. Upon meeting GrandMasterDomlyPants™, I was entirely certain that he was out of my league. Strangely, he’s said he had similar feelings about me. Somehow, we muddled through all that. Three breakups, and over a year later, we managed to break through all of that, and hook up. That hook-up became the most fulfilling and healthy relationship of either of our lives. :o)