From Pickup Artist to Pariah

Painting: Edward Hopper, American 1882-1967 Sunlight in a Cafeteria, 1958 oil on canvas/ Courtesy of Yale University Art Gallery Bequest of Stephen Carlton Clark, B.A. 1903

Jared Rutledge has been called a sociopath. Strangers have picketed outside his coffee shop, calling for his castration. People he thought were his friends won’t return his texts. There are a few places he still feels safe: weekly lunches with his grandma, his therapist’s office, the meetings of his peer-facilitated men’s support circle. At night, he reads fantasy books and loses himself in a universe with societal rules unlike the ones he broke here in Asheville, North Carolina.

The scandal that resulted in Jared’s self-imposed house arrest started in August, when an anonymous bare-bones Wordpress blog entitled “Jared and Jacob Said” appeared online. For a few weeks, no one noticed. Then, on a Friday in September, someone Jared didn’t know posted the link on Facebook.

That night, C., a redheaded woman in her late 20s, saw the link to the blog. She glanced at it long enough to understand that it had something to do with Waking Life Espresso, a popular West Asheville coffee shop owned by Jared Rutledge and Jacob Owens. C. and Jared had had a six-month fling in 2012; she’d just gotten out of an abusive relationship, and Jared, with his brown curls and his philosophy major’s curiosity, seemed like the perfect candidate for some strings-free fun. Her experience with him had been such a refreshing example of no-drama casual sex that when several friends asked her about Jared after matching with him on Tinder, she told them to go for it. Her friends went on to sleep with him, too.

The next morning, C. scrolled through the blog on her phone, trying to make sense of what she was reading. It seemed that Jared, with Jacob as his wingman and sidekick, had a secret online life as a member of the pickup-artist community. The pickup artist’s most familiar incarnation is Neil Strauss, author of the 2005 best seller The Game: Penetrating the Secret Society of Pickup Artists. But since The Game’s publication a decade ago, it’s evolved into a thriving constellation of blogs and sub-Reddits offering obsessive overanalysis of dates, economics-inflected gender theory, and men’s-rights rants. The sites are known, collectively, as the “manosphere.”

One of the central tenets of the manosphere is that there is a “red pill/blue pill” dichotomy permeating the world. The image comes from The Matrix, when Morpheus challenges Neo thusly: “You take the blue pill, the story ends. You wake up in your bed and believe whatever you want to believe. You take the red pill, you stay in wonderland, and I show you how deep the rabbit hole goes.” You can either unquestioningly accept society’s fictions — blue-pill thinking — or grasp the true power that comes from taking the red pill and facing the painful truths that most people deny. In the manosphere, the red-pill truth is that men are victimized by a contemporary culture that is biased toward the female perspective. Reddit’s Red Pill community, which has more than 100,000 subscribers, is devoted to “discussion of sexual strategy in a culture increasingly lacking a positive identity for men.” There’s also a Red Pill Women group, with 12,500 members, which sums up its philosophy as “Find a good man and defer to him.” At their most innocuous, these sources provide men with tips for becoming more self-confident and assertive; at their most toxic, they include casual racism, rants against age-of-consent laws, and blog posts entitled “Why Women Shouldn’t Work.”

Rutledge had become enamored with the manosphere after reading The Game in 2013. The following year, he started an anonymous blog and Twitter account under the handle Holistic Game (tagline: “Putting the sweet D in the tender V since 2013”). He also recruited Owens, his friend and business partner, to start a podcast. The format was simple: The two men sat on a leather couch in Jared’s living room, drinking whiskey, riffing on their dating experiences, and offering advice to less-skilled men. Jared’s blog posts offered dating tips, braggy descriptions of sexual encounters, angry venting about women who’d flaked on him, and pseudointellectual analysis of gender relations, all aimed at an audience of like-minded men.

Even as Jared tried to build a following in the manosphere, he hid Holistic Game from his friends and customers, with the exception of Jacob. Then, last August, someone — it’s still not clear who — created “Jared and Jacob Said,” which meticulously built the case that the guys behind Holistic Game were Jacob and Jared from Waking Life and then proceeded to lay out the men’s most offensive social-media musings. (Most of the comments were Jared’s; Jacob participated in the podcast but didn’t write any of the tweets or blog posts.)

It was difficult for C. to reconcile the respectful, bearded philosophy major she’d dated with Tweets like “I hate girls ‘I do everything but fuck on the 1st date’ rules. Hard to hide my disdain. My cock was in your mouth, why not the pussy bitch.” They must have the wrong guy. Then she started reading a post titled “A Breakdown of All My Lays.” “I’m going to analyze my own experience with women in order to shed some light on what women are really like,” Jared had written. What followed was a list of his sexual conquests, evaluated with a numerical score that ranked each woman’s face, body, and personality, as well as a brief description. There was something horrifyingly familiar about number four: “Frisky little redhead, early twenties. Not very hot and talked too much … I bailed on her because I wasn’t that into it. I see her from time to time, and she’s letting herself go a little.” C. screamed so loudly that her boyfriend jumped out of the shower to see what was wrong.

Word of Jared and Jacob’s double life online was spreading across town. Women who’d slept with Jared, including C.’s three friends, found themselves picked apart on his list: “damaged goods”; “headed towards cat lady status”; “not very hot.” Sarah Winkler, a coffee-shop employee who had worked for Jared and Jacob for two and a half years, read their analysis of “female behaviors” and assertions that “logic is not a woman’s strong suit” and immediately quit. Asheville is a small, tight-knit community; pretty much everyone I spoke to knew someone on Jared’s list. “I was so upset, because I had vouched for him,” C. said. “And then it’s like, ‘Who were you? Who are you?’”

I had assumed that Jared’s online persona was a kind of garden-variety lame-dude sexism, something that was more disappointing than threatening. But the night before I met him in person, I read all the blog posts and tweets together, one after another, and started to feel queasy. (Jacob did not agree to meet with me.) There was a casual aggression mixed with a strong undercurrent of contempt: “There are few things that give me more sadistic pleasure than witnessing the ever-increasing neuroses of a woman hitting the wall,” he tweeted. (“Hitting the wall” is manosphere-speak for aging.) And: “I grow increasingly weary of women’s utter inability to be self-aware and communicate like an adult. I’m just going to start yelling at them.” And: “I’d care way less about Mexican immigration if their women didn’t look like sunburnt cane toads. More Spanish, less indigenous.”

Jared lives in a tidy West Asheville house he owns. Tallish and good-looking in a generic way, with weary eyes, he had on jeans and the blue-checked button-down that New York had just that week named “the shirt that every man owns.” A painting of his great-great-great-great-grandmother, prim and Puritan in a starched collar, looked down on us as we talked in the living room.

“I indulged in cynicism and bitterness,” he told me right away. “And that’s what I’ve been working through for the last month and a half. What are the causes of it inside myself?” He spoke with the careful words of someone who has been recently therapized. “What made me —” he’d start to say and then catch himself. “That’s not the right way to say it, because I chose it. When I talk about causes, I don’t want it to sound like a justification.” And: “I should use I statements.”

“All of my life I have looked for certainty and attempted to make sense of the world,” he said. That search for an explanatory framework led him to the manosphere, where his tendency toward judgment was amplified and given direction. “It’s like a rut in your brain. I’ve had this my whole life, in different arenas. Anger and judgment. Road rage or being mad at a customer who annoyed me. The actual thing to fix is why do I feel the need to — mentally or verbally or on Twitter — punish someone with words because they slighted me. The root of it is the need to judge the world because it doesn’t meet my expectation.”

Jared grew up in West Asheville. On his blog, he described his father as “reasonably beta”: “He has long struggled with feelings of rejection and worthlessness, and had no idea how to teach me to be successful, cool, secure, or charismatic. The outcome-independence, charm, and confidence I’ve been slowly learning through game was completely lacking in my upbringing.” The family attended a Baptist church until Jared was in eighth grade, when they switched to a Pentecostal church where religious ecstasy was encouraged — Jared spoke in tongues during more than one service — but sex was taboo. In ninth grade, he and some friends discovered how to download porn on school computers. They sent some of their favorites to the principal using an anonymous email address but were ratted out by a classmate. Jared was suspended for a week. “Walking into chapel the next Wednesday was hellaciously shaming,” he wrote in his public apology after the Holistic Game scandal broke. “It felt white hot. To know that everyone in that gymnasium was disappointed and disgusted in me was almost unbearable. But I’d brought it on myself, and there was nothing for it.”

In college at the University of North Carolina–Asheville, he majored in philosophy and confidently told atheist friends they were going to hell. He was still a virgin, but he diligently studied sexual how-to videos. After college, he spent two years in Australia, studying music in a Christian creative-arts school, learning about coffee, and finally losing his virginity at age 24.

In 2009, after moving back to Asheville, Jared opened Waking Life Espresso, a coffee shop meant to double as an intellectual meeting space; it’s named after Richard Linklater’s trippy philosophical movie. Informal philosophy-discussion groups regularly met in the back room. Jared was pedantic and exacting about his coffee. Nearly everyone I interviewed, even those who are fantasizing about terrible things befalling Jared, spoke wistfully of Waking Life’s coffee. Within a few years, Waking Life was selling its popular flash-chilled iced coffee through many local retailers, including Whole Foods, and planning to open a second location. (Jacob became a co-owner in 2014.)

In 2012, Jared simultaneously split up from his long-term girlfriend and lost his faith in Christianity after a family tragedy that he prefers not to talk about. Freed of constraints, he was eager to experience all that the world of sex had to offer, but he kept striking out. Then he discovered The Game. Strauss’s book detailed the Pick Up Artist’s (PUA’s) carefully honed techniques for seducing women, including the “neg” (mildly insulting a woman to lower her self-esteem so she’s more receptive to your advances) and “peacocking” (wearing an ostentatious accessory to attract attention and project confidence). The book was a revelation. “It wasn’t that I read it and was like, ‘Oh my gosh, I want to do magic tricks in front of women,’” he said. “It was more like, ‘This is figure-out-able.’ I didn’t have the skill set to achieve the outcomes that I wanted, but I could learn it.” Attempting Game techniques in the real world didn’t always go smoothly, such as the first time he attempted a neg on a date. “This woman mentioned that she was the youngest, and I said, ‘Oh, that makes sense. You are kind of entitled and princessy.’ She got very offended and it totally blew up the date, and that was that.”

But as Jared continued to explore The Game and the online world it inspired, he found plenty that was useful. “You learn how to flirt and you learn how to talk to women and you learn how to say things in ways that don’t make them feel uncomfortable anymore. I hit on a tremendous amount of girls where, if I had done it three years ago” — before learning about The Game — “they would have been like, meh. But they weren’t that way when I hit on them,” he said.

I spoke with a number of women who were involved with Jared during these years — some as one-night stands, others for as long as six months. None of them wanted an exclusive relationship, and all of them felt okay about how things had gone with Jared before they read his descriptions of them online. “Men [in Asheville] in their 30s have, like, two part-time jobs and four roommates,” one told me. “They don’t grow up.” In this context, Jared stood out. “He had his own business,” another woman told me, “and that was something I liked about him.”

Before long, Jared’s sex life was like a part-time job. While some PUAs try to rack up as many one-night stands as possible, Jared was after a series of regular sex partners, what’s known in the Red Pill world as a harem. He hit on customers and friends, suppliers and strangers, women on Tinder and women on OKCupid. He had sex with women in the apartment above the coffee shop and in the garage out back. He created a spreadsheet that he updated with each conquest, color-coded based on how he met them and how the relationship ended. As soon as a new partner walked out the door, he’d rush to the computer to add her to the list, the thrill of quantification merging with the thrill of the chase. In 2012, he slept with three women; in 2013, 17; in 2014, 22. In manosphere terms, he was spinning plates — keeping multiple casual relationships going at once.

The most popular PUAs have online empires with e-books, coaching programs, and tens of thousands of newsletter subscribers. Jared had vague hopes of monetizing his newly acquired skills when he started Holistic Game in 2014. “I didn’t write those blog posts or tweets for women,” he said. “I wrote them for men. I wrote them for other men in this corner of the internet to validate me and make me feel good.” Jared intended Holistic Game to be a positive, thoughtful contribution to the Red Pill universe. Early on, he wrote posts with titles like “Baudrillard’s Hyperreality and the Manosphere” and pointedly countered some of the worst Red Pill tropes about how women are sinister creatures who only want to humiliate men. He told me that the more hateful and racist parts of the manosphere disturbed him; he just appreciated the dating advice: “You eat the meat and spit out the bones, you know?”

If Jared had studied his foundational text more closely, he might’ve been able to predict what happened next. By the end of The Game, Strauss has a revelation: The systematic, quantified pursuit of women tends to make men bitter and resentful. (Of course, Strauss apparently didn’t internalize his own revelation either. Earlier this year, he published a new memoir, The Truth: An Uncomfortable Book About Relationships, detailing his reimmersion in sexual conquest and shallow relationships, which also ends with redemption and lessons learned.) And so, even as Jared was getting what he purportedly wanted — plenty of sex with plenty of women — he became increasingly bitter and judgmental. Over time, his anger became directed not at a particular woman who flaked on him but at women as a group: “The hardest thing in game,” he tweeted, “is not hating women for how fucking stupid they can be.”    

Asheville doesn’t seem like an obvious place to encounter the manosphere’s particular flavor of aggrieved masculinity. The town, nestled at the foothills of the Blue Ridge Mountains, was deemed “America’s new freak capital” by Rolling Stone in 2000, thanks to its high proportion of crystal healers, anarchists, and various inflections of hippie. It’s a place where you can find flax milk in the coffee shop and have your pick of Wiccan covens. At the organic vegetarian teahouse, I heard a man tell a woman, sincerely, “It’s like the yoga of eating.”

As the news of Jared and Jacob’s secret life continued to spread on Facebook, the men issued ham-fisted apologies (Jared: “Most of my life I’ve struggled with insecurities around dating”; Jacob: “I love women”) that only seemed to make things worse. They proclaimed that they would donate the coffee shop’s profits for the rest of the year to Our Voice, a local rape crisis center; Our Voice rejected the money and issued a statement saying that the organization “is not in a position of absolving them for their misogyny as it perpetuates a culture of danger to all women and girls.”  

Some Ashevillians took a boys-will-be-boys attitude, arguing that Jared and Jacob were just talking the way men talk when women aren’t around. But for the most part, the judgment against them was swift. The owner of a local gallery who had been friendly with the two men stopped selling their iced coffee. Another small-business owner called Whole Foods and suggested it do the same. A few dozen people picketed outside Waking Life, holding signs that read I AM A WOMAN, NOT A PLATE and DON'T BUY THEIR COFFEE OR THEIR APOLOGY. Jared had uncomfortable conversations about his personal life with his family members. “You know,” his grandmother told him, “we’re women too.” The online discussion got so heated that one local yoga instructor created a special series of poses to enable forgiveness and shared it on Facebook. But, said Jared, “Nobody reached out to us to say, ‘What do you need to heal, to be better men?’ — except Trey.”

Trey Crispin is 45, with a graying man-bun and a gentle manner. He’s also the size of a fullback. Back when he was a professional snowboarder, he regularly snapped his boards in half with the force of his moves. Later, he learned how to control his own strength through the practice of t’ai chi. Having worked on his own anger issues for years, he says he is precisely attuned to other people’s aggression and sensitive to when it seems misplaced.

Like most other people in Asheville, Trey found out about Jared and Jacob via Facebook. He looked through the blog and the tweets and felt repulsed. He had never met the men or been to their coffee shop, but for some reason the story stuck in his head.

I met Trey at his house in downtown Asheville. His aesthetic could be summed up as “enlightened masculinity”: wind chimes on the front porch, the thick smell of nag champa in the air, Indian ragas playing on Pandora. He made us green tea and steel-cut oats with almonds and turmeric. Within ten minutes, he was teaching me chi exercises.

A couple days after Jared and Jacob were outed, Trey heard that, as he put it, “an angry mob” of protesters had gathered outside Waking Life. The idea of his community tearing itself apart troubled him. He sat at his wooden dinner table, musing, as the sun set. What would it take for men to use such abusive language? Where was their rage coming from? Was there a way to turn this scandal into an opportunity for growth?

“I’ve made mistakes,” he told me. “Big ones. And I was taught what community means here. I have an ecstatic-dance practice in this town. I contra-dance in this town. I play music in this town. This town taught me what community is — how, when you fuck up and you bring it to a group of your contemporaries and listen with an open mind to the other minds that you share your space with, you can work it the fuck out.”

That evening, Trey tried to dream up a way forward that would honor the harm that had been done but prioritize healing over vengeance. In Trey’s vision, the coffee shop would stay open, with all profits going to nonprofits that combated violence against women. The Waking Life men would organize community circles — groups of men and women who would get together and talk, vent their frustrations, and, he hoped, learn from one another.

He contacted Jacob and Jared with his idea through Facebook, and the two men agreed to meet with him at the coffee shop the next evening. It had been three days since the scandal had broken, and the two men looked feral, hunted. They hadn’t been eating; they smelled bad. Trey told them to sit down and asked them to explain what they’d done and why. Every time they offered up an excuse or rationalization, Trey filled the room with his shouting. “He’s a big guy,” Jared told me. “I’d never been sat down and yelled at like that by a man before.” By the end of the evening, Trey believed that Jared and Jacob were sincerely interested in the hard work of self-examination and earning forgiveness. “That night, I felt like I had hope for the first time in about 72 hours,” Jared said.

But when the men floated their plan publicly, they found that the community was not receptive. Trey approached a number of local organizations, but none wanted to be part of his gender forums. Protesters continued to congregate outside the shop. By this point, all of Waking Life’s employees had quit; two of them said in a statement on Facebook that “money can not be used to mend broken trust, absolve one of accountability, or assuage the weight of personal guilt.”

Trey says he received threats for trying to help Jared and Jacob; he took them seriously enough that he didn’t sleep at home for a few days. On October 5, Jared and Jacob announced that they were closing Waking Life Espresso for good.

“If you’re going to say you’re a loving, supportive community and then just kick out everybody that does something fucked up — I think that’s wrong,” Jared told me. “You don’t get to say, ‘We’re loving and supportive and inclusive’ and not put in the work to be that. ”

The men found themselves shunned from their other community as well: The manosphere turned on them for their public apologies. “They revealed themselves as fearful little men scrambling to be PC and do damage control,” one poster wrote on the Red Pill sub-Reddit. “The apology was pathetic and he tried to paint himself as a victim. It’s like if your girlfriend caught you masturbating would you scramble to hide the evidence and apologize or would you look her straight in the eyes, without stopping and ask if she’s going to help you finish or go away?”

Jared told me that the day before I first met with him, he saw a very attractive woman in the grocery store. He knew exactly how he’d approach, the joke he’d make about the wine label, the first steps in establishing a rapport. “I knew that if I went and talked to her, it would probably be well received from the way she looked at me,” he said. “But I didn’t, because I’m terrified of saying anything to a woman in a flirtatious way in Asheville right now.”

Still, having spent weeks in the depths of self-examination, he wondered when he’ll be able to reemerge in town as the new, humbled version of himself — and on what terms. He admitted repeatedly that what he did was wrong: “I used fucking nasty language. I used hurtful and violent language. I shared things I should never have shared about lovers and I objectified women and broke them down to box scores in a way that is objectifying and gross.” But he doesn’t want to apologize for sins he doesn’t think he’s guilty of. Some of his blog posts and tweets discuss sex acts tinged with violence — choking, belt-whipping — but Jared said everything was consensual and mutually pleasurable. “I don’t want to perpetuate rape in any way,” he said. “But I can’t neuter myself along the way. I can’t toss away my sexuality in the same way that Christianity taught me to do.”

 He is also still trying to figure out which Red Pill principles he can keep. The manosphere helped him gain confidence and release him from feeling ashamed of his desires. He still talks about The Game fondly, dropping the definite article as if it were an old friend: “I’m not going to throw away the good parts of game. I’m not going to throw away the fact that now I know how to flirt, I know how to teach, I know how to have fun.”

I asked him if he still wanted to follow the plan he’d written about in his pre-reflection-and-repentance era: fuck around as much as possible until age 38, then marry a 24- or 25-year-old. “Yeah,” he said without hesitation. “Derek Jeter’s doing it.” I must have looked incredulous. “It’s kind of a double standard, right?” he said. “Because everyone’s okay with him doing it, nobody has a problem with that.”

“Why do you want to marry a 25-year-old?” I asked.

“Hotness, absolutely,” he said.

I pointed out that 25-year-olds eventually become 35-year-olds, and then 45-year-olds.

“Here’s the thing,” he said. “There’s scientific evidence that when a male commits to somebody, in his brain they’re always as attractive — I’ll send you the study.” You can’t tell from the recording, but I’m pretty sure I put my head in my hands. “Why does that provoke such an emotional response in you?” Jared asked.

I wasn’t even sure how to begin. All the PUA dictates and manosphere Reddit threads were crowding my head with their stupid acronyms and their reductive explanations of evolutionary biology. Manosphere principles presume that heterosexual relationships are a zero-sum power game where men and women are always operating at cross-purposes. I was starting to wonder if maybe they were right. “I’m open to change,” Jared was saying. “Maybe I’ll be 38 and I’ll marry a beautiful 50-year-old CFO that can just kick my ass and ties me up. I’m open to new information always. I think that’s where I got off the mark a little bit with this. I thought I had the answer — but the answers I thought I had hurt a lot of people and hurt me.”

On my last night in Asheville, I met four women at a downtown bar. All of them were on Jared’s List of Lays. Over cocktails and ramen, the women told me about Jared’s sexual habits, his occasional flakiness, his black-and-white worldview. (They also asked me not to use their names.) They seemed most troubled by just how fine he had been to date. “I really liked him,” said W. “And that’s what makes me feel so gullible.”

He hadn’t tricked them by cheating or falsely professing love; they’d all hooked up with him knowing the relationship was casual. “I knew he was dating other people. I was, too,” said W. Jared would ask her to parse mixed messages from other women: This girl had bailed on him twice; what should he do?

“He wanted to talk about dating strategy all the time,” said L.

“One time I asked him something about texting my ex-boyfriend,” agreed K. “He emailed me a 40-page PDF about men and women.”

If anything, they said, it was Jared who wasn’t able to take the sex casually. Now they know that when a woman turned him down or canceled a date or otherwise didn’t live up to his expectations, he lashed out online. And in some ways this betrayal was worse than anything he could have dished out had their encounters been full-blown love affairs. “Having my heart broken by someone I never had an emotional investment in — it’s awful,” said C.

Several of the women told me they didn’t leave their rooms for days after the List of Lays came out and that their relationships with other men in their lives suffered. C. stopped sleeping with her boyfriend temporarily, feeling self-conscious about what Jared had said about her: “[The blog] says that I’d really let myself go, which brought up little bits left over from having an eating disorder. It’s like, don’t fuck with my life.” And K.’s on-again, off-again boyfriend broke up with her, she thinks because of what was said about her online, and she’s stopped dating entirely. “I’m mad at all men right now,” she told me. It didn’t help that the women now realized that there was a whole teeming internet full of Jareds out there. “I didn’t even know this sphere existed in humanity,” said K.

After the scandal broke, several of the women started a private Facebook group to collectively process the disorienting experience of seeing their private lives — including one of the women’s first experience with anal sex — put up for public consumption. A week or so after finding each other online, some of the women got together in person. Many had never met before. “You’d think that meeting up with a bunch of people who’ve had sex with the same person you have would be awful,” said C. “But instead it was like, look at all these wonderful ladies.” The scandal had left W. feeling ashamed and embarrassed for being susceptible to Jared’s manipulations. “I started realizing that he said so many of the same things — things I thought were genuine — to so many of us.” Meeting the other women helped her realize she wasn’t a fool: “It was comforting to see that so many good, reasonable people fell for the same thing.”

Some of them have continued to meet; these days, they talk about their boyfriends and their jobs just as much as they talk about Jared. “It’s so hard to make friends after college,” L. said. “So in a weird way, it’s been a kind of gift.”

The other positive thing to come from the scandal is that Our Voice, Asheville’s rape crisis center, has received donations from around the country and implemented a new program to combat sexism in the service industry. “There’s so much misogyny in the world, particularly in the service industry,” said Sarah Winkler, the former Waking Life barista, is opening a coffee shop of her own this year. “This was clear evidence of that. All women were affected by it, whether your name was on the list or not.” Winkler worked with Jared for years; if they weren’t friends, they were at least friendly. When I asked her about Jared’s attempts to become a better man and be reaccepted by the community, she sighed and looked sad. “There needs to be time for the community to heal, and time for the healing within them … They needed a lot of growth.”

The women who dated Jared are less interested in his evolution. “He doesn’t deserve a fresh start,” said W. “I never want to see his face again.”

Painting by: Edward Hopper, American 1882-1967
Sunlight in a Cafeteria, 1958
oil on canvas
Courtesy of Yale University Art Gallery
Bequest of Stephen Carlton Clark, B.A. 1903