Dating a Hacker Is a Dark Web

SkillUp/ MatiasDelCarmine
The reality of dating a hacker is more like Mr. Robot than we'd prefer.

Editor’s Note: This story from author Kelly Clay was originally published on Playboy.com in 2018.

We were sitting at my round, oak coffee table, 2 Macbooks, 4 cellphones, 2 large iced coffees and a few bottles of water cluttering the space. It was “early” for us, about 2 p.m. The sun was shining bright through my floor-to-ceiling windows. I was on my second bowl of Fruit Loops, but he was much healthier than I was, grazing on fruit and drinking water at a pace I thought I would drown if I kept up with. He was working on ordering something online, a small order, under $10 dollars. We never did anything on my computer, mostly because I said I was terrified, and also because I was trying to learn. I mirrored every movement he made until it became a federal crime.

Suddenly, the order went through. He leaned over and kissed me.

Adam and I met only a week ago on Tinder. His profile was deep, and he was cute. I sent him my classic pickup line, which works on most every guy who matches with me. We talked almost 24/7. I couldn’t stand not to see him for a week, so one night I suggested meeting halfway at the casino part of a fancy hotel.

He already had divulged much of his hacker behavior. Most of it was actually social engineering, which I’ve admittedly done a few times for financial gain. The more I told him, the more he told me. The more he told me, the riskier his behavior was in front of me. That night, he used an app on one specific machine to win over $4,000 in about 30 minutes. We spent that night in the honeymoon suite. Checkout was 12 pm, but Adam managed to convince them to let us leave at 4pm.

He moved into my apartment two days later. I quickly acclimated to his life; staying up until 4 am, waking up around 1 pm. But our schedule wasn’t anything like what you see of hackers in movies or TV: We both showered, made a Starbucks run, went to a store or two if we needed to, started dishes and laundry, read the news, and usually by 4 or 5 pm, when we were both awake, had what he called “morning sex.” (He was NOT a morning person. I was lucky to get a kiss good morning when I finally yanked him out of bed.)

The sex we had–two or three times a day–was actually so hot that he suggested I make a wishlist on Victoria’s Secret of underwear I’d be comfortable wearing while we work. We looked at the site together and liked the look of boyshorts with a bralette…a look I used to wear while working from home as a freelancer until an ex-boyfriend made fun of my bra collection. Suffice to say, Adam loves sex–perhaps more than his hacking.

The primary reason he asked me to get involved was his loneliness. I knew a lot about what he was doing already, in theory. If he wanted to buy me $300 of lingerie, I wasn’t going to complain. But he wasn’t going to buy it; He was going to pay for it with a stolen credit card and personal information he bought from the dark web. And that’s what Adam does. He lives for free, using others’ personal information to buy what he wants. Sometimes it’s just one small purchase under $10. Others it’s $300 to test the card. Other times he’ll do a full account takeover.

Adam negotiates the costs of these accounts with bitcoins. The entire market functions on bitcoins, because they are anonymous. No one will ever know who bought the credit card information used to make that small $10 purchase. And no one will ever know Adam made it because he secures his computer with a VPN and then makes the purchase inside a virtual machine running Windows inside his Macbook.

Adam also used this same setup to sell Adderall and a few other uppers. The market he used was–when we were dating–extremely volatile. I eventually decided things needed to end because of a fight we had, and that’s when I found out they closed the marketplace he had been using for years and was one of the most well-known dealers. He lived in constant fear that everything he needed to make a killer income would be ripped from him–the platform that allowed him to sell $1,000 of Adderall a day.

He managed his fear by carrying around an Altoid tin box that was really pills of 1mg of Klonopin. I didn’t count, but he must have opened it 5-6 times a aay; a surefire sign of benzodiazepine dependence. He was also on Lexapro, a medication used to treat bipolar disorder. His mood was most unstable towards the late night hours, when stereotypical hacking happens.

In our life, this was when his abusive behaviors started to kick in. He would call me stupid, a hypocrite, start gaslighting me, and reference my weight–a sensitive topic, and he knew it. He knew I wouldn’t go to bed without him, but I can’t take my own medications until it’s time to sleep. By midnight, I was unmedicated and volatile, so I would lash back and an abusive cycle would start, much to his benefit.

Adam was great at manipulation. We were shopping once, for example, and there was a journal he wanted. He grabbed a $3 tag from a keychain and attached it to the journal, then scanned that barcode at self-checkout. No one ever questioned him because the system registered an item scanned and then placed in the bag.

Another example of how Adam socially engineers companies–but not quite hacks them–is how he managed to convince a tech company that he had ordered a product and it was faulty, and they were going to send him a new one because he had stolen a barcode off of one when we went shopping for toilet paper one day. He’s done this before with cameras, computers, cell phones and the list goes on. He finds the barcode, and hops on chat support for hours with the company, furnishing numbers that legitimately exist but aren’t his.

Sometimes he gets a replacement. Other times he gets credit.

Every time it takes patience. Sometimes I yelled at him it wasn’t going to work. He just kept telling me, quietly, patiently, to wait. And it did.

I never got involved because I never could bring myself to use someone else’s credit–or their bank account, in the event of an ACH drip–to pay for things I needed or wanted. Sure, I’m broke. Freelance writing is not a lucrative job, and sometimes I have to find another gig to make it work, but I have standards. I lasted as long as I did with him because I was curious, and to be clear, I wasn’t even thinking of a story in it yet. But we did set up a lot of the programs on my computer because I wanted to see how much work it would take, and I can attest that if someone is serious about hacking, the amount of privacy you need to ensure you use on your computer AND your phone takes days. No one can just grab a credit card and start using it. You’re really, really idiotic if you do.

The darkest part of being a hacker is the fear Adam lived in. When we discussed our financial split, he said he doesn’t mind paying for everything as long as I help, and when I asked, he said he needed help with his store. I didn’t understand it, and then he would mention how he “figured out” why his marketplace has been so volatile.

When he left my apartment after being convinced I would kill him in his sleep–the paranoia he lived with was very, very real–I found out his marketplace was shut down overnight. The same night he thought I would kill him. I know he suffered from extreme anxiety and bipolar disorder, but how paranoid was he? How dark was Adam’s mind, one in which he imagined his girlfriend, who did nothing wrong, was suddenly going to kill him?

He doesn’t know I know, but in the week he lived with me, he had lost everything, and these kind of guys would rather keep losing everything than try to find an answer. They cycle into the same old patterns, including the same types of social engineering, the same abusive of prescription drugs, and the same use of women as sexual objects, rather than sit back and change their behavior.

I ended up buying that Victoria’s Secret order myself. My next boyfriend will probably appreciate it more, after he buys me dinner with his own credit card–and then takes it all off, so we can actually have morning sex in the morning, before we do something that doesn’t involve a federal crime.

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