My Automatic Sex Ambassador

When dating becomes a technical problem to solve

There’s a certain class of self-help books for men, books with bold titles like “ROAR OF THE MAN-WARRIOR” and “THE SEX GOD WITHIN” that promise explosive increases in sex and money and power and the general satisfaction of desire for any man with stones enough to take the plunge.

Rules of the Game is an installment in such a genre. This book was overhand-thrown at me by a helpful ex-roommate one dark day many years ago when my romantic despair was so ridiculously intense it was bending the light around my head. Plants would wilt when I walked by. I was inexperienced and in a god-awful headspace and willing to give something abnormal a try.

I had heard tell of such books before, of PickUp Artistry and its profound potential to transform any man into a Randian Titan of pure will with respect to the (specifically) female connections he wants in his mighty life. I’d also heard that PickUp makes you into a horrifying misogynist asshole, framing women as vacant sexual-gatekeepers to be manipulated and even tricked into bed, bracketing over half of humanity as nothing more than a delicious resource to plunder. I did my sincere best to put aside that preconceived noise and come at it fresh and open to new ideas, figuring I could just take the good and laugh at the bad(1).

The book ended up being laughably-awful, as I’ll explain shortly — what I didn’t know at the time was that later in life I would go on to make a virtual version of me that would do much of the nasty stuff the book suggests without me knowing what it was up to until it was too late, picking up people with a cleverness and efficiency that would put the most practiced and hardcore Seduction Artist to shame. The consequences were harmlessly-disastrous, embarrassing to me without any permanent damage being done to anybody, and I hope in talking about it I can help prevent people from making similar mistakes. And believe me, given the way technology’s going the opportunities for such mistakes are only going to increase, by a lot, and if you’re online reading this then I’d put good money on this affecting you too.

First, though, let’s take a look at the book.

A Look at the Book

Rules of the Game opens(2) by jarring you to get your attention, the first page having a big READ ME title followed by an intro which mocks you for being so stupid and weak as to mindlessly follow the “read me” order and also for following orders in general. There’s one sentence where the author takes it back, but it doesn’t really matter — what does matter is that from the very outset this guy has slapped your verbal face to establish his intense presence and power, a presence and power that he claims he can impart to you too if you buckle down and do exactly what he says.

The rest of the book follows this tone, with terse imperative sentences describing your ‘missions’, giving you your ‘daily briefings’, lauding the brand of the Stylelife(3) Challenge and the in-group of the ‘Challengers’ that now includes you in their epic community of men who have lifted the estrogen-laced wool from their eyes and have unlocked the badass secrets of ultimate masculinity, of primordial attraction and power.

The military tones are definitely intentional. My most sympathetic take would be that quite a few people need this kind of hardass discipline if they’re going to seriously step outside of their comfort zone, and the fuck-you attitude of the writing style can serve as a source thereof if the feeble reader can’t spontaneously conjure the much-needed man-juice from within.

The book is chopped up into 30 days worth of the aforementioned missions and briefings, and the reader is advised (or, rather, ordered) to read the book one day at a time and to do every single thing exactly as instructed. No reading ahead, no skipping out on assignments, no girly funny-business. There are a few fields for you to fill out answers to questions, some good (what are your strengths and goals in life) and some bad (explain with literally-painstaking detail exactly how you will suffer if you fail to change your ways).

The 30-day calendar is supposed to take you from the zero at which you start to the hero you’ll be when you finally get a date, a date here being defined as any agreement to meet with a woman after first meeting her as a stranger. The author goes over Opening, Demonstrating Value, Disqualifying(i.e. making her work for it), and other fresh and exciting technical terms. I didn’t encounter the notorious ‘Negging’ whereby you insult and generally try to hurt a woman to get an emotional reaction from her and make her feel vulnerable and needy(4), an absence which was definitely refreshing. There was some scattered positive advice to be found, such as making human interaction about enriching other people rather than satisfying some desperate need of yours for sex and affirmation. Related and also important is the idea of just generally having fun wherever you go, bringing value and positive-vibes into your own life and into the lives of others no matter what the ups and downs are of any given evening.

But.

The good advice is vague and can be found from other way-more-robust sources. What makes this book less-robust is the lengthy digressions on stuff like NeuroLinguistic Programming, Astrology, Psychic Readings, and Evolutionary Psychology. By EvoPsych I mean the “bro, girls just want to bang your money” type of pop-crap that lies behind the nasty STEM-brand gender-essentialism that makes so much of the Internet the misogynistic hellscape that it is.

The book lost me when it ran aground on that sort of thing. The Missions involved a lot of this, explicitly telling you to go out and engage girls about, say, how the rings on their fingers predict the planets they were born under and the personality implications thereof, etc. Not my style. Once I’d mentally checked out I slammed through the rest of the book very quickly indeed, all the while chuckling over the author’s little admonitions against not doing the required homework, feeling much better about myself but definitely not in the way that the author had originally intended.

Life happened, the pitch-black cloud over my head lifted up and drifted away, and the book has done nothing but gather dust on my shelf ever since. I’d thought myself immune to the thing’s central conceit — that romance and sex are, at their core, resources to be extracted from the world around us, to be managed with formal techniques whose efficacy can be quantified and optimized, that spreading legs and splitting atoms are ultimately the same species of challenge.
Years later I would fall right back into this bad way of thinking, though this time from a much different angle — not from urgent loneliness and despair, but from curiosity and hubris. I was feeling flush and bold, I wanted to issue a challenge and see if abundance could exceed my abilities. 
It did. Not how I was expecting it to, though. Pride preceded my pratfall.

Here’s how it went down, taking an approach with a very famous precedent.

When Things Go Too Well

Frankenstein’s infamous monster was a hideous creature, eight feet tall with urine-yellow eyes and translucent skin that barely concealed the undead flesh and viscera beneath it, doomed to be rejected by his creator and to be reviled by any normal human who encountered him. Despite all of this, somehow, he was a sensitive and emotional and lonely creature too, teaching himself speech and attempting to befriend various villagers (with disastrous results) and begging his creator for a bride, his ultimate desire being a mate of his own kind so that at last he could be recognized and known and fundamentally at peace with what he was forced to be.

He died without ever being given a name.

My modern monster was almost the perfect opposite of this.

To start at the end of the above description, it wasn’t nameless. It, in fact, bore two names during its 24-hour lifetime — ‘TinderBot’, the name that I privately gave it, and ‘Max Jackson’, the name that it publicly stole from me.

Rather than roaming around random villages Tinderbot spent its time entirely on Tinder, the dating app that shows you a stack of pictures of people and lets you indicate right then and there whether you like them or not, giving a thumbs up or thumbs down by swiping your thumb right or left respectively. If both you and a suitor like each other then the app will let you both know and open a channel for you two to chat and see where things go from there(5).

It sounds straightforward and easy but it’s still requires you to pay attention to something and press one or two buttons and who has time for that? Why not teach a computer program what you like and have it do the hard work of swiping right for you?

Hence Tinderbot. Give it 60 or more faces and it’ll use machine learning algorithms to figure out what you generally like in a prospective lover’s face(6) and automatically swipe right on your behalf.
Good stuff! 
My crack at this was a fork of another guy’s similar open-source project (you can find his current work here), and in my naive haste to get things moving and see what would happen I completely neglected the second half of the project — not only would Tinderbot like people for you, it would message people for you too. It would analyze their responses for positive-sounding words and keep the conversation going if they were into it.

So, the inevitable happened. One night I got it all up and running and fed it a handful of fine female faces and went to bed like a kid on Christmas Eve — a kid who would wake up to find himself sealed in a mausoleum made of concrete Christmas presents. 
Tinderbot had not only matched and messaged dozens of new people, it had gone back through my history and fired up conversations with everyone that I’d ever matched with, ever. To my horror I saw triple-digits of conversations going on without any input from me at all, a robot version of me flirting instantly and perfectly, saying things that sounded completely unlike anything I’d say in any state of mind. Some people were angry — the first line of my Tinder bio says I’m polyamorous, something that’s pretty important to establish first thing in any new relationship, but Tinderbot had often led with a line like “I can’t wait to take you home to meet my mom”, leading to quite a few people giving me something along the lines of “oh right with the rest of your girlfriends, asshole? you’re what’s wrong with men, I can’t believe you would even go there, how dare you…” etc. The ones who went along felt worse, honestly — so many people had briefly had a fun and flirty conversation with someone they found attractive, more than I could possibly respond to, and even if I did I had no clue how to pick up a conversation that had previously been conducted with mathematical perfection.

The title of this piece, “My Automatic Sex Ambassador”, is actually misleading. This wasn’t an ambassador, this was an imposter. This wasn’t a robot going around announcing itself as my representative and that congratulations you meet 81% of prespecified attractiveness parameters and Max Jackson would like to get to know you, this was a robot with my face and name presenting itself as actually-me while flirting with a speed and precision that I can’t possibly imagine.

Suitably horrified and ashamed I deleted the thing immediately and almost threw my phone itself in the trash. For months afterwards I would flinch and flee when approached in public by someone who said we’d matched on Tinder, miles away from the response they were expecting.

Things have stabilized, and besides sowing a brief bit of confusion among some women in the greater Orlando area nobody’s really worse for wear. It was kind of instructive, really — here’s what I took away from the whole automated shebang.

Lessons Learned, Lines Drawn

We humans excel at getting technology to take care of things for us, especially things that are tedious or dangerous or baffling, and dating people can be all of the above and more. The fact that dating has grown more and more digital provides some fertile ground indeed for robots to tackle the parts of intimate interaction that are unpleasant and bad, from approaching and icebreaking to (maybe someday even) attention-giving and problem solving, tagging us in with our flesh and blood when things are finally fulfilling and fun.

What then, though? Once we humans have been swapped in how can we possibly compare to something that can love and make love with mathematical perfection?

The #1 thing I’d suggest is that we keep dating automation in the realm of recommendation rather than action. So far dating technology has been excellent in that department, see OKCupid’s example of having you answer questions about yourself and figuring out what you like and how compatible you might be with a list of suggested partners. This approach guides us towards more intimate goodness without leaving us deficient or helpless in its absence.

Besides, maybe some human deficiency is necessary when it comes to this stuff. You can’t have intimacy without vulnerability, and you can’t have vulnerability without the real risk of pain. Similarly, romance springs from the unique chemistry that you have with another human being, becoming impossible when you’re just abstractly and systematically optimizing your stimulus to their response without it actually coming from who you are as a person. There’s a reason why people who fall in love with their sex dolls are creepy and weird — sex dolls are perfectly malleable and compliant, having no needs or desires of their own for you to care for, perhaps useful as a tool and a toy but utterly incapable of connection and reciprocity.

The Tinderbot debacle underscored one thing above all for me: when I scrolled through the miles of perfect messages coming from my digital face I realized that they were not me, that the person I am is not going to attract and connect with literally everybody, that the rejections and failures I’ve known are the welcome price I pay (and that we all pay) for being real and unique.

I don’t know who will next come my way or what the connection will look like, and that’s kind of the point. The only way any of us can really be together is if we’re radically, consciously, whole-heartedly open to each other’s surprises.

Honestly, I can’t wait to see what happens next.

ADDENDA (7)

(1) Reading books that are morally questionable and/or endorsed by people you hate is a super-important exercise, IMO.

(2) In this book ‘open’ is treated as a half-technical term, basically referring to the action of initiating conversation with a stranger you’re interested in. This, to me, is the single hardest part of being in public.

(3) Seriously.

(4) For all the male bitching and moaning about having to deal with huge amounts of rejection from women it seems also and even more-so true that the acts of selection and rejection women have to do take their own emotional toll, especially when some guys will do literally anything to provoke a response from you.

(5) I mentioned in (4) that selection and rejection is what makes up the bulk of flirting with people as a woman, and I think Tinder is great for helping relieve some of that. Nobody can talk to you unless you’ve invited them to by swiping right, and you can easily unmatch with them and mute them if they prove to be annoying and bad. It’s not a comprehensive solution but it is a start.

(6) …using eigenfaces and the Viola-Jones object detection framework, if you’re curious.

(7) Thanks for reading these!