I am Bad at Flirting; Realizing that by Noticing Confusion

by snog toddgrass 4 min read30th Jun 20207 comments


This post is about applying rationality to my dating life. It is gooey and rich in self-disclosure. But it was a great triumph over motivated reasoning.

I notice my confusion

When I was 22 I that my romances began mainly when I was busy. They began most often, paradoxically, when I was unable to pay attention to my interest in early courtship. The observation was interesting but did not then replace my preferred explanation for romantic successes and failures.

At the time I subscribed to, what I call, the “mental health” hypothesis[1]. When I was healthy and confident women could sense it and chose to date me. Sometimes I became “unhealthy” and women became disinterested. Partners sensed “unhealth” by uncontrollable micro-cues. Thinking about dating will only make you more self-conscious and worsen your chances. This explanation agreed with the results of my favorite epistemology: asking my female friends what they think happened (critique of this method). At the time I had not learned Bayes theorem, Occamian reasoning or any social influence literature, so the “mental health” hypothesis seemed plausible. Besides, I liked my earlier beliefs. I just need to be “better” then women will like me. It was a simple, appealing narrative. If Iost that explanation, the alternatives might be “you must be a jerk” or “you are unattractive”, which scared me. Besides, Me_2016 did not know the benefits of saying “oops”.

By 2019, the “mental health” explanation was under increasing strain. The conventional advice was to make your life full by exercising, working on your mental health, improving your career, and the partners will come”. The problem was that it did not work, despite soundind wise. In the Summer of 2019 I was healthy,4; I had a good job, strong friendship networks, passionate hobbies, and plenty of exercise. It was the ideal time to seek a partner and I put great energy into the search. Despite my apparent health, I had the worst results in years. When I pointed this out, my poor friends could only shake their heads and think “there he goes, trying to solve the unsolvable.”

The nail in the coffin of the “mental health” hypothesis came that winter. I lost my job, was briefly jailed in a foreign country, and emerged into a revolution and a currency crisis to look for work. That same month I broke my back and worked myself into an emotional collapse. And women loved it. I got more positive response that one month than 5 months in nest-building mode. Something else was going on. I finally noticed my confusion.

This summer I reinvestigated with Bayesian reasoning. First, I had to choose between believing two unlikely statements. Either this pattern of relationships was a strange coincidence, or my female friends had no idea what made them choose who to date. The first conclusion seemed unlikely, as from the 15 or so courtships I remembered the three successes occurred during strenuous efforts to hide my interest. That pattern is unlikely if relationships occur randomly. The second conclusion had seemed wildly implausible at first. But after reading about a mountain of cognitive bias and the difficulty of rationality, the unknowability of our preferences made sense. I began talking to my friends about how they selected partners. I mostly found their responses to be nonsensical, either drawing on overcomplicated psychological constructs or qualities that did not seem special at all.

Furthermore, the “mental health” hypothesis relies on partners “seeing through me”, through just a few social cues, postures, and inflections, to a deep, hidden but somehow well-defined part of my psyche where “health” information is stored. Such a complicated theory should have a low prior. A low prior with no evidential support…

Availability is the problem

And a challenger appeared. In the summer of 2019, I accidentally invited three young women on the same hike[2]. I was so worried about offending them that I called my mother for advice. She suggested hitting on none of them during the hike, so as to be fair. My mom was an unintentional genius. I started seeing one of the women from the hike the next week. That partner later stated that she was honestly unsure if I was interested until we first made out, with particular reference to the hike. I suspect that forcing myself to now lavish attention on my interest made me a much more appealing partner[3].

The simple solution I call the availability hypothesis. Potential partners respond to how available I appear, when deciding about a first date. If I signal that they can have me easily, partners do not want me (as much/usually). I have two aligned explanations for the phenomenon. Firstly, partners enjoy the uncertainty of not knowing if I am interested or not. I become a challenge to be achieved. If I just tell someone they are great, then they have achieved that status and only get the pleasure once. I can also give subtle but incomplete signals of interest, each of which provides a separate rush of pleasure. So the person who knows I like them is less likely to come to my party, respond to my messages, notice my cool hobbies and passions, and generally fall in love with me.

Secondly, there is status competition. If I signal that dating me is easy, they perceive my cost as low. Amateur jewelry shoppers assume expensive jewels are valuable, because assessing the value of each piece independently would be tiring and difficult[4]. Likewise, how available I am is a simple value heuristic for prospective. This explanation may be an unflattering, but people do seem to care a lot about social status.

Note, they are not responding to neediness. Healthy, confident availability is right out as well. Partners are responding to the “price tag” I present. If I say in the first meeting that I like a person, the chance of a relationship drops, whether I say it confidently or needily. Words like “desperate” misleadingly imply that there is a healthy, flirtatious way to express unambiguous interest. The correct strategy is to be ambiguous[5]. In the words of one ex, you should have “General Aloofness”.

I suspect the optimal amount of interest is just enough. Slightly less than your prospective partner is ideal, but slightly more interest may be necessary as women rarely initiate. I must learn to imply interest without ever making it explicit. In other words, I was coming on to strong the whole time.

An agenda for further experimentation

There are many more tips to learn. Good posture improves attraction. Eye contact. A good fashion sense goes a long way. A few gestures at traditional masculinity. Teasing seems highly rewarded, so I can learn that. After all, 12-year-olds master the art.

My next step is to keep experimenting and reading. Less wrongs posts have been useful, especially this one. Send along any reading recommendations in addition to HughRistick amd Lukeprog and Minda Myers. This work by Scott Alexander is illuminating, and Eric Raymond wrote the simplest guide. Wish me luck!

[1] I put mental health in quotes to emphasize its vagueness in this context specifically.

[2] The hike was not an attempt to make anyone jealous. I had simply observed that most people I invited hiking flaked, and so began inviting as many participants as possible.

[3] There is also evidence that women are influenced by peer attention. See Sprecher, Wenzel and Harvey, 2008. The Handbook of Relationship Initiation, pp. 103

[4] Cialdini, R (200). Influence: Science and Practice [4 .ed]. See chapter 1.

[5] Also, desperateness is a more complex/poorly defined category than availability. Cialdini’s work suggests people prefer simple heuristics.