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Chapter 7: Hacking Relationships

You can’t understand relationship hacking without appreciating something about geek identity.

Published onApr 03, 2019
Chapter 7: Hacking Relationships

In 2005 a little-known subculture was placed in the spotlight by Neil Strauss’s best seller The Game: Penetrating the Secret Society of Pickup Artists. The book’s central character is an aspiring illusionist who goes by the stage name Mystery. For years Mystery had been a prolific contributor to online seduction forums. There, pickup artists (PUAs) discuss their theories about seduction and post field reports of their real-world sorties. The Game portrays the inception and unraveling of Project Hollywood, a group of PUAs living in Dean Martin’s former Los Angeles mansion. Tynan, digital nomad and self-help superhuman, was a participant in the project, and he writes that the latter half of the book portrayed “Mystery and I teaching workshops, me stealing his girlfriend (twice), Courtney Love moving in, my second attempt at going polyphasic, and a bunch of other great stories.”1 The book was a sensation because its stories of masculine hijinks and dissolution can be read as tabloid, character study, how-to manual, and cultural indictment. It has something for everyone.

Many of the men portrayed in The Game capitalized on the book’s popular reception—even if much of that attention was critical. Those running seduction seminars and workshops expanded their businesses. Tynan followed with Make Her Chase You: The Guide to Attracting Girls Who Are “Out of Your League” Even If You’re Not Rich or Handsome. Mystery wrote The Mystery Method: How to Get Beautiful Women into Bed, which was followed by a VH1 reality show.2

Mystery describes his method for seduction as an “algorithm for getting women.” The only math most of his readers care about are the digits “of the girl in the tight sweater,” but an algorithm is key to a solid game, and he claims, “I invented that algorithm.”3

Life hackers use systems and algorithms in every domain of life. Recall Paul Buchheit’s belief that “our entire reality is systems of systems” and that “wherever there are systems, there is the potential for hacking.” As evidence, Buchheit cites Tim Ferriss’s kickboxing, Seth Roberts’s health hacking, and The Game.4 Even within computer hacking, social engineering is a potent security exploit. Hackers use impersonation and guile to convince targets to reveal their passwords. If computer security can be hacked with social engineering, why not social interaction itself?

The idea that everything is a system calls to mind the expression about everything looking like a nail to someone with a hammer. This aphorism has a handful of variations, including Abraham Maslow’s 1966 musing: “I suppose it is tempting, if the only tool you have is a hammer, to treat everything as if it were a nail.”5 Thinking about life hacking in light of this has two virtues. First, it highlights the power of metaphor: in life hacking, systems can be understood as games and hacking as a tool. Second, Maslow’s Hammer implies a critique: that possessing a tool can distort one’s vision and lead to the tool’s being misused. Hacking is a powerful tool, and for those that believe reality is “systems of systems, all the way down,” everything appears amendable to its force. But as we will see, overreliance on a tool can lead to heartache.

“Why I Will Never Have a Girlfriend”

You can’t understand relationship hacking without appreciating something about geek identity. To be a geek is to be outside the mainstream, often ensconced in a subculture. Geeks are not, stereotypically, known for their social skills; rather, their defining traits are intelligence and their enthusiasm for computers, games, and comics. Geek identity, then, is characterized by feelings of insecurity and superiority relative to the mainstream, often simultaneously.6

This juxtaposition is seen in a 1999 classic of internet lore, “Why I Will Never Have a Girlfriend.” In it, Tristan Miller, a computational linguist, presented “a proof, using simple statistical calculus, of why it is impossible to find a girlfriend.” He dismissed the possibility that there was “some inherent problem with me.” It wasn’t awkwardness or a lack of fashion sense; rather, it was a matter of numbers: there aren’t that many suitable women. Miller began his calculation with the requirement that a woman must be two standard deviations above the norm for beauty; she must also be intelligent, but she doesn’t have to be as intelligent as she is beautiful. After further winnowing by age, availability, and reciprocal attraction, Miller was left with thousands of possible women across the globe. But these gems were lost in the population at large; if he went on a blind date with a new woman every week, it would take over three thousand weeks before he dated one of these women: “we can safely say that I will be quite dead before I find the proverbial girl of my dreams.”7 Miller wrote this, tongue-in-cheek, almost twenty years ago, and it shows how insecurity about having no girlfriend can be masked with the pretense of superior mathematical reasoning.

Today, on the bitter fringes of online culture, men speak of being “incels” (involuntary celibates). In time, they might take the red pill (a reference from The Matrix), awaken, and join the other MGTOW (men going their own way). The Rational Male, also the title of a blog, is trapped in a system in which his desires are either ignored or exploited by the likes of gold diggers.

Pickup artists, though, have not yet lost hope. They believe that the AFC (average frustrated chump) can be transformed into an alpha male. (Masculinist culture is laden with pop-culture references, jargon, and abbreviations.) The PUA uses his reasoning to discern the patterns of seduction and to learn the algorithm by which his desires can be fulfilled rather than exploited.

Scholars of this subculture believe that these feelings of insecurity are potent. Matt Thomas argues that pickup and life hacking attract the same sort of “white male geek” and that a “post-industrial ‘crisis of masculinity’” underlies both. Pickup artists cope by hacking seduction: “They have reversed engineered it and reduced it to a series of steps, scripts, and procedures that any man—theoretically—can follow and be successful.” “Is it any surprise,” he asks, “that Tim Ferriss and Neil Strauss are friends? Or that one of the episodes of ‘The Tim Ferriss Experiment’ is about him learning how to pick up women? Or that in that episode Ferriss consults with [computer] hacker Samy Kamkar?”8

Complementing the geek’s insecurity is a sense of rational superiority, sometimes manifesting as braggadocio. Upon discovering pickup culture, one famous computer hacker wrote: “I’m what PUAs call a ‘natural,’ a man who figured out much of game on his own and consequently cuts a wide sexual swathe when he cares to.” Fortunately, other hackers “don’t have to be helpless chum in the dating-game shark pool. We have some advantages; with a little understanding of human ethology we can learn how to use them effectively.”9

Learning how to deploy their geeky advantages is what Mystery offers his readers.

I was a geek, too. The truth is, generally speaking, geeks are intelligent individuals who simply haven’t yet applied that intelligence to social scenarios. … When you look at all other human beings as beautiful, elegant biological machines embedded with sophisticated behavioral systems designed to align with others to maximize their chances for survival and replication, the task of understanding humanity and your place in it becomes surmountable. … With me as your friend and guide, you’ll start uploading Venusian arts programming into your behavioral system and then practice and internalize it so you won’t have to think about picking up.10

In short, the successful pickup artist is a reformed geek, one who has reprogrammed his behavior to hack that of others: insecurity gives way to superiority. The self-help sell is that the average frustrated chump will be frustrated no more, with the right tools in hand.

The Origins of Pickup

Mystery’s claim that he invented the algorithm for seduction is disingenuous. He did, however, make significant contributions to its latest iteration. As a performer, he brought flare (known as “peacocking”) and new routines for establishing rapport with strangers. He excels at eyeliner and feather boas, at parlor tricks and mind reading. But modern pickup culture can be traced back at least fifty years.

There were two things about the 1970s that gave rise to pickup culture: the sexual revolution and the computer as a metaphor for the mind. The sexual revolution meant that people could more easily engage in sexual trysts. Eric Weber’s 1970 book How to Pick Up Girls spoke to the man who could have sex outside of marriage but didn’t know how to make it happen. Weber assured his readers that “normal, healthy young chicks like sex” and they “will be glad to have sex with you if you only ask them.” For example, peace rallies are great places to pick up “fantastic broads,” “even if you’re [privately] for war.”11

Weber’s book is deeply creepy and written from the perspective of male entitlement and female objectification. Weber infamously begins the book with a scenario of seeing a woman walking down the street: “You’ve just got to see more of her long legs. Her fine rounded breasts. Her high, firm behind. For an instant you even consider rape.”12 This dark legacy persists in pickup today. In language, women are objectified and quantified by way of a 1–10 “Hot Babe” scale. In practice, one pickup guru who endorsed psychological abuse and physical coercion was banned from traveling and teaching seminars in some countries. Pickup manuals have also been banned from the Kickstarter crowdfunding site because of similar concerns. This is self-serving and other-harming ideology, sold as pickup tips and relationship advice. Beyond the harm done to its targets, it warps the attitudes and character of those who read it.

In addition to increased sexual opportunities, popular culture in the 1970s reflected the growing power of computing. Although computer matchmaking can be traced back to Harvard undergrads in 1965, computing’s contribution to pickup in this period was by way of metaphor. Much of the theory behind pickup is an extension of neuro-linguistic programming (NLP), which began in the 1970s as an attempt to identify the techniques of successful therapists. NLP was cast in the mold of ascendant technology: language was a way of programming the neural machine. It claimed to be the “art and science of excellence” and promised that the communication skills of “top people” could be learned by anyone.13 Much of NLP understands the self and communication as maps or models, shaped by stepwise processes.

NLP has since been discounted as legitimate psychotherapy; one scholarly review characterizes it as “cargo cult psychology.”14 Nonetheless, it has been influential among self-help gurus, including Tony Robbins. Scott Adams, creator of Dilbert and self-help author, readily acknowledges NLP’s influence. In an interview with Ferriss, Adams traces his interest in persuasion and hypnosis back to these roots and recommends that listeners think of their lives as a system. He begins his book How to Fail at Almost Everything and Still Win Big by explaining, “Your mind isn’t magic. It’s a moist computer you can program.”15

Even though NLP was intended as a means of self-improvement, it was most tightly embraced by those wishing to seduce others. Ross Jeffries, a proponent of “speed seduction,” incorporated NLP and hypnosis into pickup in the 1980s. With the help of a computer hacker, Jeffries also took his approach online, founding the Usenet group in the 1990s. Many pickup gurus, including Mystery, got their start there. Jeffries continues to be active in the scene today—and a little resentful of the attention the latest generation of gurus has received.

The overlap between NLP and pickup is seen in their shared concepts, including accessing cues, anchoring, mirroring, and reframing. For example, accessing cues are eye movements that reveal internal mental states. Mirroring builds rapport or reinforces behavior by mimicking others’ subtle behaviors. Jeffries’s uses these notions, and the suggestive power of metaphors and homophones, throughout his writing. In a 2011 blog post, he wrote of a hypnotic-like interaction with a German woman, his friend’s assistant. When Jeffries spoke a little of his high school German, she complimented him on his pronunciation. He responded: “I find languages have a certain feeling and a CERTAIN SHAPE IN YOUR MOUTH. When it’s right you can FEEL IT IN YOUR MOUTH.”

She thought about it a moment and said. “That’s very true. I speak a little French and it feels much different in my mouth.”

I said, “That’s right. French is very soft. But German is VERY HARD IN YOUR MOUTH.” (This time I leaned on it a bit and put more of a sexual tone to it.)

Her pupils dilated for a moment, she took in a deep breath, and visibly reddened. As she did I gently nodded my head “yes” and she mirrored it back, nodding gently in return without being aware of it.16

Because he had a girlfriend, Jeffries practiced “hook ’em, catch and release,” but he encouraged his readers to try to use the same techniques in their conversations with women. Practice makes perfect even if—at that moment—you aren’t able to follow through.

Jeffries’s story is a weird combination of crassness and pseudoscience. Language is powerful, but it’s not magic. Conceiving of the brain as a computer and a relationship as a system has both advantages and limitations. The idea that we can change ourselves and our surroundings is a useful one, but it can be taken too far. I doubt dropping “new direction” into a conversation is going to make women more receptive to a “nude erection,” as Jeffries suggests. I suspect the German woman was simply being polite to her boss’s friend.

In this way, seduction hacking is like some of the claims of health hacking: marginal science is overextended to questionable applications via anecdotes and testimonials. Nonetheless, for the lonely and systematic thinker, the allure of behavioral patterns and systems is obvious.

Optimal: Two Bisexual HB10s

People are desperate to reduce life’s complexity, and this is not limited to men or hackers. Whereas Jeffries released How to Get the Women You Desire into Bed in 1992, Ellen Fein and Sherrie Schneider published The Rules: Time-Tested Secrets for Capturing the Heart of Mr. Right in 1996.17 In the latter book, readers were encouraged to become “rules girls” by following thirty-five precepts for attracting and keeping a husband—the books’ gender stereotypes complement one another nicely. Despite Fein’s marriage’s falling apart during the release of The Rules, she and Schneider followed with other rules-based relationship books. Fein, of course, blamed her divorce on not following her own rules.

Even if rules-based approaches to relationships are not unique to men or the new millennium, they are more potent in the twenty-first century. The excesses of rating others and of treating others (and yourself) as rules-based “wet machines” is facilitated by the ease of quantification and optimization. In the 1970s, the metaphor of programming was enough to shape how people interacted with one another. Today, actual programs shape our interactions—as we like, swipe, and rate others on our smartphones.18

In the search for human connection, bedding an HB10 (a 10 on the “Hot Babe” scale) and capturing a successful man become goals that are optimized toward ill-fated ends. If there is a moral to The Game, this is it. The drama of Strauss’s book is the alpha male’s crash after his elation at no longer being a chump. Strauss succeeds as the PUA known as “Style,” but in doing so realizes that “all the techniques that are so effective in beginning a relationship violate every principle necessary to maintaining one.”19 Seduction can be the near enemy of connection. Additionally, even the goal of getting laid or finding a girlfriend, he found, had been displaced by the need to maintain his status among his male peers. Strauss later declares himself a sex addict and checks himself in for treatment—the topic of his next book. Mystery ends up in a psychiatric hospital as his failed pursuit of having two bisexual girlfriends—both 10s, ideally one Asian and one blond—knocks him askew. The danger of optimizing is that it is easy to fixate on that which is tempting, quantifiable, or easy at the expense of other goals and values.

Skilled programmers are actually sensitive to this danger. Although people naively use terms like programming and optimization, junior programmers are warned that “premature optimization is the root of all evil.” When coding, it is easy to fall into the trap of optimizing something without appreciating whether it is causing an actual performance bottleneck. It’s like perfectly dicing your onion with a well-honed blade without ensuring you have all the recipe’s ingredients first.

Those who design optimizing algorithms especially appreciate this point—they speak of local optima that fall short of a global optimum. Imagine you are blindfolded but wish to find a tall hill within a specified region. A naive search algorithm is to take steps only forward or up; you will likely find a hill, but probably not a tall one. So designers intentionally introduce fuzziness into their algorithms and allow them to wander a bit, even if it means sometimes going downhill before reaching a higher peak. Naive optimization often yields suboptimal results, and optimal results often require some flexibility—a point I’ll return to at the end of this chapter.

An experienced and skilled life hacker might be able to design a well-balanced and globally optimal system. This is what Nick Winter attempted when hacking his productivity by also tracking health and social goals. But such a system is unlikely for anyone other than the dedicated hacker who is willing to quantify and optimize everything. Otherwise, the danger of optimal hacking is to naively optimize on finding an HB10 or a successful husband. For many, such goals are not easily achieved, and when reached, are found to be shallow and unsatisfying.

To put this in terms of Maslow’s Hammer: if you have an optimized hammer, it will serve brilliantly for pounding a screw into drywall. The problem is that when you stand back to enjoy the picture you just hung, the screw is not likely to hold.

Nominal: The Challenge of Being Likable

Not everyone wants to optimize toward a harem or wealthy husband, but many still lack the skills and confidence for more modest aspirations. To this end, hackers take on challenges as a step toward even the nominal goal of not being alone.

Challenges are a favorite tool of the life hacker. For example, surviving a cold shower lends a sense of efficacy independent of, but transferable to, other life goals. Similarly, the shy and hesitant can undertake rejection therapy. In pickup, approach anxiety is countered by repetition. A student will approach a dozen women in an evening, with the possibility of receiving as many rejections. In the process they learn, become less fearful, and possibly succeed. This is not limited to pickup. One life hacker sells decks of cards with challenges, which can be used alone or as part of a game with others. The “Entrepreneur Edition” includes “30 unique suggestion cards designed to expand your comfort zone and your wallet.” For example, “Ask for one month free from a service provider.”20

Unlike a lot of pickup books, Tynan’s are not focused on manipulation. Make Her Chase You and Superhuman Social Skills are thoughtful—and systematic—suggestions on how to be a likable person. His goal is to teach the reader “how to share the best parts of you in an honest and authentic way.”

In this book, I will be unabashedly analytical, examining and quantifying aspects of social skills that are usually not spoken about. We’ll talk about power dynamics, our value as friends, opportunity cost, and efficient use of time. Whether or not we acknowledge these, and other, factors, they underpin our social interactions and play an enormous role in the quality of relationships in our lives. Some find these topics unpalatable, or even offensive, but it’s hard to make a better sausage if you don’t take a look at what’s going inside the factory.21

Even if this approach is analytical, Tynan’s aspiration is humane. How can we reconcile Tynan’s mission with the unpalatable PUA tactic of negging?

In The Game Strauss defines negging as an accidental-seeming insult or backhanded compliment: “The purpose of a neg is to lower a woman’s self-esteem while actively displaying a lack of interest in her—by telling her she has lipstick on her teeth, for example, or offering a piece of gum after she speaks.”22 This was the sort of negging critiqued by Randall Munroe in his webcomic XKCD, popular among geeks. In a 2012 strip, a man attempts to neg a woman in a restaurant (figure 7.1). He notes her fruit plate and says, “You look like you’re on a diet. That’s great!” She turns the tables and blisters the PUA (life hacker) with disdain, telling him that his epiphanies about productivity, creativity, and connection are hopeless because his mediocrity is inherent.23

Figure 7.1 Randall Munroe, “Pickup Artist,” XKCD, 2012,

As a fan of XKCD, Tynan felt obliged to respond. He conceded that there are plenty of assholes, within pickup and without, male and female: “Bad people exist.” Yet the point of a neg, contra Strauss, is not to undermine a woman’s confidence. It is, instead, a way of showing you’re not intimidated, that you’re willing to relate to someone in a joking and teasing way, as you would among friends. Tynan finds the woman’s response in the comic harsh but appropriate “given that she was just approached by a random stranger and tactlessly insulted.” Even so, he finds the comic to be cynical and hypocritical because it implies mediocre men should be left to suffer—and inflict themselves on others—without any hope of improvement: “When a guy is faced with the harsh truth he has to improve himself to have a better dating life, he can either ignore that and dismiss pickup wholesale, or he can begin down the difficult road of learning social skills, understanding women, and becoming the kind of guy that girls want to be with. That’s what pickup is.”24

That’s what pickup is, as long as it avoids the excesses of optimization. Make Her Chase You provides interpersonal tools for the man seeking to be attractive, even if “not rich or handsome.” As the catchphrase from the home improvement parody The Red Green Show states: “If the women don’t find you handsome, they should at least find you handy.” In this case, handy means good with the tools of self-presentation and interaction. Tynan seeks to teach the unskilled how to use these tools, increasing utility and safety for all. However, when they are weaponized and used as a means of maximizing the quantity and optimizing the “hotness” of the women seduced, pickup deserves the criticism it receives.

Data and Dating

Amy Webb, a “quantitative futurist,” was saddened and disappointed by the breakup of her last relationship. Sadness is expected when someone who was once close becomes part of the past, but her disappointment was related to the future. She had just turned thirty, and the prospect of starting over imperiled her plans for a family. In a popular TED talk, “How I Hacked Online Dating,” Webb spoke of a calculus similar to that behind Miller’s explanation of why he had no girlfriend. In Webb’s estimation, there were only thirty-five men of a similar age, “Jew … ish,” not interested in sports, living in Philadelphia, and whom she would find attractive. If she wanted to find such a man, she could no longer rely upon happenstance. She would have to go online.25

But if online dating improved Webb’s chances of finding Mr. Right, it also increased her exposure to the Mr. Wrongs. After a series of bad dates, including one who abandoned her with an exorbitant dinner bill, she realized she needed a filter.

Webb’s philosophy is that of a hacker. When faced with a problem, she says, “I’m going to use some data, run it through a system, and get to a solution.” She devised a rating scheme of differently weighted traits, divided into two tiers, and set a minimum threshold. Among first-tier traits, being cigarette and drug free was worth ninety-one points. On the second tier, a height between 5'10" and 6'2" was worth fifty. She would no longer waste her time on anyone with a total below seven-hundred points. Problem solved—except it wasn’t. She might have cracked the code for finding a Jewish Prince Charming, but he never messaged her back.

Webb’s calculations hadn’t taken into consideration that she was competing with other women. Her profile of frumpy photos and text pasted from her resume wasn’t working. So she created fake profiles of ten men she would like to marry and analyzed the attributes of the popular women contacting these fake accounts. She found that her competitors’ profiles were short and nonspecific and used optimistic language. They had nice photos, which showed a bit of cleavage or shoulder. When she applied these insights to her own profile, she became the most popular person on the site.

Webb is not the only one to have hacked online dating, been the subject of popular attention, and followed with a book. Two years after he was profiled in Wired, Christopher McKinlay published Optimal Cupid: Mastering the Hidden Logic of OkCupid.26 OkCupid matches people based on user-created questions and answers. Like Webb, McKinlay used fake profiles to collect answers to common questions from thousands of women. He used these data to identify and target clusters of women he found appealing and tailor his approach, without being deceitful, so he would be similarly appealing.

Although Webb and McKinlay both created fake profiles, Webb to assess competitors and McKinlay to target candidates, their approaches differ in a significant way. McKinlay gave little thought to winnowing the chaff. He did rank his candidates, but he also went on eighty-eight dates before finding someone he would begin a relationship with. In the end, he considered the endeavor a success, but it sounds exhausting.

If only there were a way to delegate some of this work, which is what Tim Ferriss naturally did. Whereas others made use of spreadsheets and code, he used outsourcing. As a way to get attention for The 4-Hour Workweek, he delegated the finding and scheduling of dates to competing teams throughout the world, including India, Jamaica, Canada, and the Philippines. He gave each team a one-page spec sheet with goals, guidelines, and links to women he found attractive. His teams were able to schedule twenty café dates into three days, all within half a mile of his home: “It worked extremely well. Perhaps a 70% hit rate,” which far exceeded his efforts at bars and parties.27 And it cost him only $350, including the $150 bonus he established for the team that set up the most good dates.

Online dating exemplifies the systematization of life, even for those who do not share the hacker ethos. Thanks to digital technology and its creators, we have an extraordinary amount of choice, which we manage via swipes and likes, providing a stream of data to algorithmic matchmakers. Given that hackers built these online dating systems, it makes sense that other hackers are well suited to exploiting them.

Such exploits, of course, are not without their perils, especially when it comes to the high-frequency dating of McKinlay and Ferriss. Ferriss felt bad about mistakenly giving the cold shoulder to a woman with whom he was supposed to be having a date because one of his outsourcers had neglected to put her in his calendar: “She walked right up to me, I was writing on my laptop, and started chatting like an old friend. I had absolutely no idea what was going on.”28 I imagine she felt the same, but worse. Another hacker, Sebastian Stadil, went on 150 dates in four months—topping even McKinlay. This led to some blunders, including with “a girl who had spent the entire first date telling me a very sad story about her being an orphan. On our second date, I asked her how her parents were doing. That was an awkward moment. If you’re reading this, I apologize.”29

Even so, most every hacker concluded his or her approach was a success. Ferriss, Webb, and McKinley all thought so—but they were also selling books. Stadil is the exception. He writes, “I still believe technology can hack love, though that belief is likely irrational.” Why? He confesses that “having more matches increased my odds of finding someone interesting, but it also became an addiction. The possibility of meeting that many people made me want to meet every one of them, to make sure I wouldn’t miss the One.”30 Stadil’s insight is about the paradox of choice in the digital age: with many options, it is easy to look to the horizon and imagine greener fields.

The hacking mind-set, especially an optimizing one, is especially susceptible to this pathology of the digital age. Much like the productivity hackers who obsessively hone their tools without ever getting on to the task, the dating hacker, if not careful, is liable to never move on to the task of building a relationship.

Yootling and Marriage

The life hacker is, above all else, a rational individual seeking self-help, even when it comes to relationships. We have already seen criticisms of this and of millionaire minimalists and philosopher bachelors. But not all life hackers are millionaires or bachelors. We encountered Heidi Waterhouse’s “life-hacking for the rest of us,” including those with kids. Dave Bruno had to distinguish between family and personal items as part of his 100 Things Challenge. Similarly, in 2012 Nick Winter had been inspired by Tynan to only have ninety-nine things, but he later acquired a wife and two kids. He does not include their stuff in his annual list. When I asked Winter how his new family affected his minimalism, he responded that his intention is to restrain his personal appetite, which isn’t a problem with baby stuff: “If I were loading up on baby toys, then I’d have to modify the rule.” He concedes he no longer has the benefits of being able to move in an hour, backpack for months at a time, or live in a tiny home, but he still appreciates having only a few high-quality things of his own.31

What happens when we move beyond stuff, toward marriage, children, and chores? In the course of his productivity hacking, Winter made use of the application Beeminder. To balance his work productivity, he gave himself social goals, such as romantic dates and platonic outings. Recall from chapter 4 that with Beeminder, if you fail to meet your goal, you forfeit your pledge to its creators, Bethany Soule and Daniel Reeves. This couple, with graduate degrees in machine learning and computational game theory, also use monetary exchange to manage their marriage.

Soule and Reeves’s unusual approach to their relationship has been featured on NBC News, and Soule is forthright about how it works on their blog. At the center of their system are the values of egalitarianism (everyone’s happiness is equally important), autonomy (everyone has their own values and can make their own choices), and fairness (equal contributors to group effort should benefit equally). The last is so important they named their daughter “Faire”—at eight years of age, she was said to be the youngest Beeminder user, tracking things like sugar consumption and screen time.32 Their son, Cantor, is named after a nineteenth-century mathematician.

In short, Soule and Reeves keep individual financial accounts and bid on things like putting the kids to bed, taking out the trash, and planning a trip. In a process similar to rock-paper-scissors, Soule and Reeves each hold their hands behind their back and simultaneously reveal a dollar amount they would pay the other to do the task—they call this “yootling.” The person with the higher number pays the loser’s bid. If Soule flashed a four and Reeves a two, Soule would then pay Reeves two dollars to take out the garbage. From an economic point of view, this is an efficient allocation. Soule least wanted to do it since she was willing to pay four dollars, and she happily pays the two dollars at which Reeves was happy to do it. (They have additional rules to simplify the record keeping, such as randomly recording only 10 percent of their yootles.) Reeves sees this as a distillation of bartering and turn-taking. For Soule, “it ends up feeling a lot more amicable than feeling each other out and making compromises, and trying to guess between what a person is saying and what they actually mean and navigating all that kind of stuff.”33

Even so, it’s not difficult to foresee where things might get difficult. Their children might be hurt to learn their parents bid on who tucks them in at night. However, given they are being brought up this way—Faire’s name was determined by an auction between her parents worth several thousand dollars—I don’t imagine the kids would be surprised. There is also the matter of producing children in the first place. Soule and Reeves don’t yootle in the bedroom, but most everything else, from the value of giving birth to that of staying at home with the kids, needs to be reckoned, which is nontrivial.

If this sounds cold and miserly, Soule explains that it is possible to be kind and generous using the system: “We do nice things for each other all the time, and frequently use yootling to make sure it’s socially efficient to do so.” For example, Reeves doesn’t have to accompany Soule to a Buffy the Vampire Slayer sing-along, but he might kindly yootle for it: “He magnanimously decides to treat his joining me as a 50/50 joint decision. If I have greater value for him coming than he has for not coming, then I’ll pay him to come. But if it’s the other way around, he will pay me to let him off the hook.”34

As geeky as this sounds, Reeves and Soule appreciate it as such. Even so, they are not alone; similar approaches have appeared in the mainstream. The authors of Spousonomics: Using Economics to Master Love, Marriage and Dirty Dishes recommends using concepts like division of labor and supply and demand to minimize conflicts and maximize the benefits of marriage.35 Whereas the Beeminder couple keeps economics out of the bedroom, Spousonomics begins with the case of an unenthusiastic woman considering the costs and benefits of sex with her horny husband.

Mismatched libidos are something that Ferriss thinks about too. He is fond of a story about a married couple and how they manage their different needs. Every quarter, the wife gives her husband a report card covering four categories: lover, husband, provider, and father. In each category, she rates him on a ten-point scale, and the husband can have a low score in one as long as he keeps the average up. Hence, if the husband succeeds at work, increasing his provider score, he can also have a dalliance, lessening his husband score. As long as the husband keeps his total score above the wife’s minimum threshold, it’s okay. Ferriss finds this “very appealing, maybe as I like measuring things as a way of course-correcting and keeping things in check.”36

If clear expectations and communication are necessary to good relationships, all of this sounds exemplary. Except as you can imagine, critics find such quantified relationships troubling—with a side of cringe when it comes to sex. The question, then, is why the discomfort?

“You Are Doing It Wrong”

When Soule and Reeves’s story of an exchange-based relationship was published, it attracted a few responses from far-flung corners of the internet. Luke Zaleski, a writer at GQ, finds the game-theoretic bidding of “these two imbeciles” to be misguided: “folks like the Pay-for-Play couple in Oregon, YOU ARE DOING IT WRONG.”37

In their defense, Soule and Reeve appreciate that their approach is unusual. It is geeky, but their app and blog has a small following among the like-minded. For such folks, yootling can feel more comfortable than figuring out the meaning behind others’ words. Perhaps Soule and Reeves are deficient in the interpersonal skills necessary for “navigating all that kind of stuff,” but it is what it is, and they are who they are. They are geeks sharing what works for them—rather than gurus prescribing their approach as best. Also, Zaleski doesn’t say much about how to “do it right” beyond alluding to sacrifice and selflessness. Reeves and Soule are not opposed to such virtues, they simply strive to make their allocation fair. For example, they explicitly recognize the value of giving birth and spending time with their kids; at least such things are not taken for granted. This approach would not work for most people, myself included, but I can’t claim they are “doing it wrong.”

Elsewhere on the web, Sarah Gould, a blogger at Catholic Insight, thinks yootling sounds mercenary. Shouldn’t love and help be given freely within a family? She also believes yootling ignores “God and the higher realities of life”: “Might this elevation of fairness to god-like status contribute to an inability to deal with the unfairness of life?”38 In her view, we ought to recognize that life is unfair but that God’s grace is freely given.

Gould’s critique is bound to a particular religion, which not everyone shares, and “higher realities” are invoked but never explained. She concedes that people need to find what works best for them and that yootling seems to work for this pair of nerds. Yet for her, reducing love to “weights and measures” would extinguish genuine gratitude and make a farce of love and a false god of fairness and money.

Even secular critics make arguments about the transcendence of human behavior and life’s unfairness. In her 2000 book Cyberselfish: A Critical Romp through the Terribly Libertarian Culture of High-Tech, Paulina Borsook wrote about this a few years before life hacking’s emergence.

With cause, many programmers are proud of the rule-based bounded universe they create; so if simple propositional logic were all that were operating in human affairs, then human affairs might very well be fixable through simple rules. But game theory, powerful as it is, can’t explain all of human behavior. … In addition, dealing in rule-based universes can put you in a continual state of exasperation verging on rage at how messy and imperfect humans and their societies are.39

However, Soule and Reeves do recognize the importance of love, selflessness, and generosity. For them, yootling is a clear and playful way of expressing these things. And just because human behavior is complex, it doesn’t mean there is a ghost in the gap between what we can explain and what we cannot. Yootling need not extinguish the deeper bonds that form from years of exchange.

Borsook, like Gould, questions how hackers face life’s difficulties, including “messy and imperfect” people. I share this question—it’s the topic of the next chapter—and it is reminiscent of an episode of Seinfeld. In “The Deal,” Jerry and Elaine discover that even with clever rules (e.g., sleeping over is optional and no phone call the next day), they cannot have casual sex and remain friends. Feelings can be hurt and jealousies stirred even within the perfect system.

Although humans are messy and imperfect, Gould and Borsook sound defeatist. If you have nails popping up from the decking of your flooring, why not hammer them down? You might miss one and later stub your toe, but that does not damn your earlier efforts. Life hackers do tend to be less accepting of imperfection than is typical, but this is both a strength and a weakness. They optimistically seek improvements, which leads to inventiveness and credulity. There are lessons to be learned from those hacking relationships, but complaints that they are too weird and ungodly do not suffice.

The most concerning thing about relationship hacking emerges when quantified and transactional approaches are dehumanizing and exploitative—which they have a tendency to be. For example, in outsourcing, there can easily be an imbalance of power, in which choice is more a reflection of necessity than preference, in which the other is objectified via market imperatives, in which deceit and opaqueness obscure the context and consequence of exchange. We see elements of this among unsavory PUAs and industrial-scale dating, but less so among mutually consenting geeks.

The Right Tools for the Job

Like any tool, some metaphors are more appropriate to their contexts than others. As I argue in chapter 1, calling life hacking a “cult” is hyperbolic, but referring to professional lifestyle advisors as “gurus” is a decent fit. What about relationships as rules-based games? Some things are more game-like than others, and some people are more likely to enjoy playing, but the metaphor is apt. We can discern rules (some explicit, some implicit), and there are elements of luck and skill. What’s more, life is increasingly game-like, given the proliferation of rating and gamification on our devices. Yet there are also assumptions about whether the game is competitive or cooperative and what counts as victory. As Strauss and Fein found, becoming adept at seducing a woman or capturing a man is not necessarily a win. Their notion of games and rules assume rigid stereotypes and zero-sum competition. Fein and Schneider’s Rule #5 is to never call a man and rarely return his calls, keeping him uncertain and insecure. A PUA playing the game might neg a woman to the same end. An alternative is to conceive of relationships as a cooperative and jointly beneficial undertaking. For example, Soule and Reeves conduct aspects of their relationship in transactional terms, but their intention is to respect each other’s “utility functions” rather than exploit them.

Maslow famously used the hammer metaphor to communicate the danger of overusing a tool, observing, as noted earlier in the chapter, that we tend to treat everything as a nail when a hammer is in our hand. A stronger version of Maslow’s intuition is that we not only treat everything as a nail, we see it as such. What, then, are some of the limitations of seeing relationships as systems to be hacked with rule sets and spreadsheets?

Consider the case of Valerie Aurora, who in 2015 returned to the dispiriting task of online dating. This time, she hoped she might make the experience palatable, fun even, by hacking dating. Inspired by Amy Webb, she developed a spreadsheet for ranking candidates on the basis of two top-level categories: “dealbreakers” and “extra credit.”40 Aurora also included five attributes of interpersonal chemistry: ease/closeness, fun, safety, mutual respect, and affection/passion.

However, a weakness of the spreadsheet approach is the assumption that an excellent match is out there and waiting to be rated and ranked. An alternative assumption is that people invest and grow in their relationship, that a good match is not found but made. Aurora eventually came to this insight with respect to her spreadsheet and dealbreakers.

My original intention for making this tool was to make me more aware of and responsive to my “dealbreakers”—things that meant a relationship wasn’t possible. But while making and using this tool, I discovered that my own ideas about what was a “dealbreaker” were frequently wrong. I am now in a happy relationship with someone who had six of what I labeled “dealbreakers” when we met. And if he hadn’t been interested in working those issues out with me, we would not be dating today. But he was, and working together we managed to resolve all six of them to our mutual satisfaction. Talking to my friends, I found that this was a pretty common experience.41

To hold too tightly to the spreadsheet’s dealbreakers would’ve been to hold too tightly to a tool not fit for the task.

Among computer programmers, there can be a similar overreliance on behavioral rule sets. Programmers often rely on what they call “patterns” of successful structures and best practices. Antipatterns, in turn, are to be avoided. The problem is that programmers can get stuck using the patterns, tools, and practices with which they are most familiar and proficient; they refer to this as the Golden Hammer antipattern—yes, overusing patterns is an antipattern.

This can be seen in the case of David Finch, a former semiconductor engineer, who chose a journal of best practices as his relationship tool. In his “quest to be a better husband” he compiled a list of best practices, which he later published as a memoir. These rules included things like taking his wife’s perspective, going with the flow, and having fun. He made great use of these practices until they started getting in the way; at that point he realized “the final best practice: don’t make everything a best practice.”42 Sometimes a favorite tool needs to be put aside.

We might put a tool away for a number of reasons. Maybe the job is done, as with Finch’s best practices. Maybe the tool is inappropriate or dangerous, as Strauss realized about pickup and meaningful relationships. Maybe it doesn’t work, as we might infer from Fein’s divorce. Maybe it needs to be used less rigidly, as with Aurora’s spreadsheet of dealbreakers. When it comes to relationships, the game really is to build and maintain something together, for which there is no single tool.


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