What You Can Learn About Falling in Love From the Alleged Silk Road Kingpin’s OkCupid

“Hit me up when you are happy, and if NO one will listen, send me a message about it” -Ross Ulbricht

When trudging through the depressing labor of online dating, our profiles offer the most obtuse, intimate, aspirational versions of ourselves—a collection of fun facts and penetrating questions laid bare for judgmental strangers.

This week, we got a glimpse at the OkCupid profile of accused online Silk Road kingpin Ross Ulbricht when his dating life was dragged in front of a jury in a series of emails. Among all of the accounts from journalists and law enforcement officers as a cryptographic mastermind, or a heartbroken tripper who scorned the world for a life of crime, his OkCupid stands as one of the most comprehensive accounts of the man himself according to himself.

So this reporter decided to take a dive into Mr. Ulbricht’s profile to find the man himself, the version he saved for someone he might have gotten close with. After all, he wanted his next relationship to last the rest of his life. It’s the Ross Ulbricht of OkCupid’s personality questionnaire—a list of questions OkCupid asks to determine if you’re a match with someone. When you go to someone’s profile, you can see a person’s answers to any question that you’re also willing to answer yourself. You show me yours, and I’ll show you mine.

So we went in and answered every single one of Ross’s questions. For about four hours, I went in and truthfully answered his 394 questions to reveal unveil each of his micro-confessions, which sometimes revealed further handwritten notes when he wanted to explain his answers.

What we found about Ross: He’s serious, compassionate, tidy and open to experimentation. As closed off as he’s been publicly, he wanted to get to know someone, even if that someone wasn’t perfectly aligned with each and every one of his values. He’s firm in his convictions, but he’s tolerant, affable, and open-minded. He’s immensely likable if you spend enough time with his information, and he was hoping to be immensely lovable—all from a profile he hadn’t visited since September of 2013, about a month before he was arrested.

Now, a word of warning: These details may seem meticulous and intimate, but that’s the nature of the OkCupid questionnaire. After all, It’s not a vast majority of people who ask themselves whether or not shaving someone else’s pubic hair would be a turn-on until they’re prompted to.

That said, let’s start with sexual compatibility, where Mr. Ulbricht and I are a 98 percent match.

Sex

Mr. Ulbricht is bold: He won’t rule out going home with you on the first date, and is “super confident” in his, ahem, abilities. He even thinks he’d be a good porn star, given the opportunity. He wouldn’t mind if you pulled out a camera and asked to be filmed during the act, except for that he prefers sex with the lights off.

As for kinks, he doesn’t want to get too crazy in the bedroom, but judging from his answers, he’ll try anything reasonable once, or at least if it’s what you need. He could even get into the idea of shaving you—though he prefers a lady who’s already neatly trimmed—and will indulge a foot fetish, even if that’s not his inclination.

He’s done some roleplaying, though he didn’t specify what, and he’s even willing to act out a rape fantasy if that’s what you’re asking for (be sure to establish a safe-word beforehand, maybe something about the malleability of anonymized transactions if you really want to get him going). He’s discreet, uninterested in a lady’s past exploits, and isn’t prone to unreasonable jealously.

“I am monogamous, so if the girl I am with wants to do anything romantic with another person, it’s out of the question,” Mr. Ulbricht writes, “but I’m not going to get all jealous for no reason.”

He calls his sex drive “average,” but to him that constitutes having sex every day. Is it easy for him to achieve orgasm? Any time the wind picks up.

And he likes to cuddle.

Lifestyle

Ross Ulbricht prefers books to music, science to art, logic to intuition. He’s a true Apollonian, unmoved by appeals to his emotions in the face of reason. He doesn’t like loud concerts, and his taste leans more “independent” than mainstream—though he doesn’t dig anything too dark or violent. He drinks occasionally, but never really feels a need to be drunk or go out clubbing. Mr. Ulbricht isn’t a beer snob, or a snob about anything by his account.

He wouldn’t say he’s “compulsively neat” either, but he keeps his bathroom spotless, and tries to pick up after himself as much as he can, when he has the time. He could date someone who was messy, but “living with them is another story all together.”

More of a hippie than a yuppie—a tough distinction when your parents have a summer house in Costa Rica, but the place has artesian walls and solar power. He admits to doing drugs in the past, including psychedelics, and says he’d be curious to try DMT—that’s dimethyltryptamine for anyone who hasn’t seen Into the Void. Still, he’s mostly stopped using any drugs, and there’s a limit to what he’ll put up with in a match.

“[T]here is lots of behavior common to drug users I wouldn’t tolerate,” he writes, “but if you can keep your shit together then I don’t care what you put in your body.”

OkCupid repeatedly asks questions about whether or not he’s stuck in his ways, to which he answers with some permutation of saying that he’s very adamant about his own views, but knows that other people need space to have their own, contrary beliefs. However, when I called myself a political Centrist, it was flagged as one of his unacceptable answers. His political affiliation was listed as “Other” without explanation, but political beliefs are definitely important to him, and he loves to argue about philosophy and religion.

Mr. Ulbricht prefers a life of accomplishment to a life of leisure, and believes that an adult should continue to educate themselves. He’d be comfortable being poor for the rest of his life, and material wealth doesn’t matter for him in a match—he’d rather have peace on earth than tons of money.

He could live without the Internet, but that his “quality of life would take a nose dive.” And he’s never been to prison. You know… yet.

Dating

Now, for all of Mr. Ulbricht’s virtues, we’re going to go ahead and say he’s a bit… choosy. Maybe it’s just high standards? If you’re looking to date Ross Ulbricht, you’re going to have to meet certain criteria:

First, you have to be in pretty good shape, and he’d prefer to date someone younger than him (he’s 30) with no leftover kids. Mr. Ulbricht wants kids eventually, but know that “there are ALOT of steps between here and there!”

He wants to be with someone “well-balanced”—more mellow than hyper—and thinks he’d have a good sense of who you are within five dates. Money or wealth don’t matter in a match, but if you’re not taking care of your body, he’ll write you off immediately, and he won’t date anyone who is transgender.

Mr. Ulbricht claims to be pretty open with his feelings, but this guy isn’t going to be a cloying boyfriend. He values his personal and emotional space highly, and his least favorite trait in a partner is decency. He prefers to show his affection through verbal communication, as opposed to gifts, favors and gestures. Which is not to say traditional affection isn’t important—he still prefers cuddling while asleep, thinks sexual compatibility is a must-have, and thinks physical contact is an important part of showing affection.

Also, this would be a good time to remind you: he’s looking for someone who’s ready for a big commitment. Dedication and passion are both vital to a relationship with Mr. Ulbricht, but dedication takes priority.

“That’s how I roll,” Mr. Ulbricht wrote. “I’m looking for the love of my life. I’ll give you a chance, but if you aren’t her I’m moving on.”

He’s been in two major relationships that had gone on for over two years, though he insists he’s not trying to retread old ground and go dating any of his exes. He “hardly ever” even thinks about them.

Ethics

Mr. Ulbricht has described himself on public social media profiles as a fan of the free-market Austrian School of economic thought. In his romantic life, the basics are the same: Mr. Ulbricht a laissez-faire objectivist who is ”not at all” trusting of the government, but who believes that compassion is a sign of strength. Just by throwing cigarettes onto someone else’s lawn, Mr. Ulbricht believes he would be insensitively devaluing someone else’s property.

“It’s almost like stealing, in a tiny way,” he writes.

Morality is universal to Mr. Ulbricht, not relative. Prostitution, animal testing, flag burning and all consenting sexual acts should be legal. Same goes for a woman’s right to choose: He doesn’t see contraception as morally wrong, and he doesn’t think a woman should feel obligated to shave her legs. He even sees an indoor ban on smoking as a regulatory overreach.

“I’m not a smoker, but I’m also not an asshole that forces his views on other people,” he writes. “Treat others as you would wish to be treated. That’s universal in my book.”

Considers himself an honorable person— he doesn’t consider himself a good liar, and always keeps his promises.

“My word is my bond, my word is who I am,” Mr. Ulbricht writes. “If I do break a promise, which does happen from time to time, I will always honor my word and respect the person I gave it to.”

He thinks that reading through other people’s mail and private communications to be invasive, which puts a whole slew of federal agents into Mr. Ulbicht’s friend zone real quick. And if someone asked him “What’s the worst thing you’ve ever done,” he says he would know right away.

The Takeaway

The more you dig into Mr. Ulbricht’s personality, the more you move toward the compromised, personal opinion of someone like Lyn Ulbricht, Ross’s firebrand mother who has become a veritable deep web analyst in attempt to clear her son’s name. It’s embarrassing to say about someone you’ve never met, but it’s hard not to love someone a little bit once you’ve spent so much time in their dirty laundry.

Even when I was tempted to blast through the questionnaire with fake answers, I kept on for hours answering truthfully, laughing or cringing at various reveals, and disappointed when he beat my expectations again and again. The process got personal, a get-to-know-you game that felt like it had stakes. I was looking at a profile he was using almost right up until he was arrested, and every new piece of intimate insight suggested that no, he’s not a sociopath, he’s not some drug tycoon. He can’t be.

But that’s what you always from personal testimony about any criminal, even legitimately guilty ones. The more you know someone, the easier it is to give them the benefit of the doubt, and harder to envision them doing something horrible, even if they’re truly capable of it.

Still, it just didn’t make any emotional sense that this person, who says they’d be happy being poor for the rest of their life, could have moved $13.4 million in cryptocurrency and discussed hiring contract killers. His charm made a chump out of me, and here I am like a Serial podcast fanatic, shouting “there’s just no way he could have done it” at my computer monitor.

Then again, I’m not sitting on the jury.