Dating Criminals

Austin woman's first date with alleged Silk Road drug lord leads her to promptly stop dating

Austin woman's first date with alleged Silk Road drug lord

Editor's note: In the excerpt below, the author refers to Ross Ulbricht as a "drug lord." Although Ulbricht was arrested this week in San Francisco on suspicion of operating a web-based drug ring that also provided false documents, hacker services, hitmen and firearms (among other things), he has not been tried or convicted.


In the winter of 2011 (or fall of 2010, she can't totally remember), Kelly Williams, then 26, went on a date with a man she met on OkCupid. They met for dinner near the University of Texas campus and exchanged pleasantries. The night took a weird turn, however, when the man took her to a frat party before getting so wasted he passed out on her bed. She wrote a blog post about it that became popular among her friends and promptly moved on with her life (she also stopped dating almost immediately).

On Wednesday, she was perusing CultureMap when she saw an article about the FBI's arrest of the alleged Silk Road architect (and fellow Austinite) Ross Ulbricht. "I saw the picture and I was like, 'Oh my God! That's the guy!'" Williams tells CultureMap. Yesterday, she wrote a funny account of her date with Ulbricht, a man accused of running an international marketplace for illegal activity, but about which not much is known. Funny, yet also tragic, this story provides a little insight into both Ulbricht and why, even when every red flag is flying, we still believe in the magic of first dates. Even when they are with a supposed criminal mastermind.

Excerpted with Williams' permission, please find her entry below. To read more, visit Williams' blog.


I've been on a few, nay several, terrible first dates, including one with this dude, supposed mastermind of the "black market Amazon for drugs" and Austin local Ross Ulbricht. There was only one date, because 1. it was awful, 2. he was awful. While the date itself was not spectacularly awful, and the guy did end up naked in my bed (but really, not what you think), I'd rank it up there in the top five worst dates of all time.

 I asked how he came to own a small book business after a graduate degree in math, and [Ulbricht] told me that he was "just a better businessman than most people." 

During our initial interactions, he seemed very intelligent, well-spoken, witty, and very charming. Not to mention, he was kind of my type- tall, dark hair, dark eyes (honestly, the linked picture doesn't do him justice, he really was better looking in person, I'll give him that). I had sincere hope that something would spark here. The only thing that was ignited, though, was my temper the next morning.

We met at a place close to my house, near the UT campus. We planned on dinner on a Friday night, but we left the plans at that. I think we were both doing the "dinner and then see where it goes" thing.

When I arrived, I was pleasantly surprised to meet a punctual and personable man who looked exactly like his profile picture. We sat down, got straight to the small talk, and ordered drinks. Did you read the linked article above yet? Because you should really do that now. The next part will be funnier if you know exactly what this guy is going down for.

When we got to the "so what do you do for a living?" part, my explanation didn't take very long. I told him I what I did. He asked one or two follow-up questions, and then we got straight to talking about him. He segued into his own about-me portion without prompting. He told me, verbatim, "I run an online book store, kind of like Amazon, but local." I asked a million questions, because I tend to do that, but he went into very little additional detail. Instead, he talked at length about going to Penn State for grad school for some kind of math degree, if my memory serves me correctly. I asked how he came to own a small book business after a graduate degree in math, and he told me that he was "just a better businessman than most people," and it was a pet project to him, not a means of making money really. So then I asked how he did make money, he skirted around that topic as well.

Next, I asked where he lived, like what part of town? He told me he lived in Lakeway, in a house. It's unusual for a mid-20s dude to own a house in Lakeway (very nice neighborhood, non-Austin readers), so I prodded a bit on this subject. He said that he lived in his parents' house while they were "away." Who knows if that was true or not? Point being, for 80 percent of dinner, we talked about him, his success in business, his grad school experiences, his travels, his ambitions, and his life in general. At least he was interesting, right?

Toward the end of dinner, he excused himself to make a phone call while I ran to the bathroom. When I got back to the table, the check was taken care of and he had his coat on. He said, "I just talked to my friend, and I had planned on going to his house after this for drinks. A few people are getting together, would you like to come, it's not far from here." I will admit, I was still kinda digging this guy, although something felt a little off. I agreed, but insisted on taking separate cars because I had work in the morning and would probably want to leave earlier than him.

 He had said "a few people getting together." I envisioned a game night with wine and cheese and eight of his closest friends. Nope. It was a frat party. 

I followed him into a neighborhood near my house and parked behind him on the street. We walked toward a house at the end of the street and I noticed a lot of cars, then more cars, then a house with people spilling into the front yard, and then heard really loud music. The closer we got, the more confused I became. I wanted to believe that we were going to walk right past it. He had said "a few people getting together." I envisioned a game night with wine and cheese and eight of his closest friends.

Nope. It was a frat party.

Mind you, I was almost 27 at the time (I think he was too), which is a not normal age to be at a frat party. If you are 27 and still actively participating in the collegiate party scene, grow the hell up. I left beer bongs and keg stands behind at the ripe old age of 22. I felt really, really out of place but I tried to hide it. He grabbed my hand and lead me to the back yard, past the horrid band playing in the living room, and a kitchen full 19- year-olds doing Jell-O shots. We found his friends there, and he introduced me. I tried hard to not look completely uncomfortable, but these people were probably not even of legal drinking age. I was the "old chick" at the frat party in skinny jeans, knee high boots, and a Colors of Benetton wool coat. Clearly I was not dressed for the occasion.

As I chatted with a very sweet, very drunk 20-year-old next to a makeshift campfire, I turned around and noticed Ross was not near me, or anywhere. He had abandoned me at this party I did not want to be at in some person's backyard after only five minutes. He came back about ten minutes later with a beer for me. Ok... he was getting me a drink, but still. Then he took out a flask from his coat pocket. Ok... perfectly acceptable, it's a party. Then he popped a pill and washed it down with the stuff in the flask.

I can make conversation with almost anyone, but that doesn't mean I want to. As I conversed with Ross's drunk friends, he kept disappearing and then coming back. Did I mention this was like January, which is about the coldest it gets in Austin? I was freezing in the back yard, nursing a beer at nearly midnight when Ross sat down next to me. "You know, I really should be going, I have work tomorrow," I said. He offered to walk me to my car.

On the way to my car, it became very apparent that Ross was in no condition to drive —or stand up. I don't know what he did when he kept disappearing, but it definitely involved more than drinking. That much was obvious. After nearly falling over half a dozen times, I felt like I couldn't leave him there. I definitely did not want him to attempt to drive. My house was around the corner, and still, at this point, I did not hate the dude. I asked if he wanted to crash at my place, and I'd take him to his car in the morning on my way to work. He said yes. We left his Subaru in the neighborhood and I drove to my place.

When we got to my apartment, I showed him around, gave him a pillow and blanket for the couch, and got changed and ready for bed. I had two cats at the time, and Ross didn't seem like a huge fan of cats. Like every other man on this planet, he claimed he was allergic. I lived in a really small, one-bedroom apartment, and the only way to confine the cats was to lock them out of the bedroom or into the bathroom. They'd be much less likely to scratch at the door if they had the entire rest of the apartment. I told Ross he could sleep in my bed, and I'd take the couch. Given our lackluster chemistry and his physical state, nothing was gonna happen at this point.

While I brushed my teeth, homeboy passed out in my bed within mere seconds. Oh, and he fell asleep in his jeans which reeked of bonfire smoke, but he weirdly took his shirt off. Ugh. In this light, passed out in my bed, I was really not attracted to him. Any initial chemistry we had, he killed when he got sloppy drunk at a frat party. Why the hell didn't I call him a cab? What was I thinking??? Whatever, I wasn't about to go in there and help him get undressed, he could sleep in his jeans. It's not like those sheets weren't gonna get bleached anyway. I went to the couch and proceeded not to sleep that much. My alarm went off 15 minutes after I finally dozed off. I, "Queen of Snooze Button," immediately got up.

I turned on lights. I turned on the TV. I opened and slammed cabinets. I took a shower in the bathroom that connected to the bedroom. I traipsed in and out of my bedroom, rifled through drawers, opened blinds, and this dude was out cold. It typically takes me 30 to 45 minutes to get ready for work in the morning, but I was so ready to be rid of this guy that I got dressed in about 15. I made coffee in a Keurig, not the quietest process, and he did not stir. I went back into my bedroom and noticed his jeans were on my floor. He must have taken them off at some point.

I picked up his jeans and threw them at his head and said loudly, "So, I have to go to work, you have to go. I can give you a ride to your car, or you can walk, it's not that far." He rolled over and said, "Is it cool if I just stay here for a little while and lock up when I leave?"


Ummm, no, guy that took me to a frat party that we were five years too late for, you cannot hang out in my home while I'm not here. WTF?

"No, you can't. I'm sorry. You need to leave. I need to be at work in five minutes." That was a lie, I had 45 minutes before I had to clock in.

He pulled his jeans off his head and groaned, like I was the one being rude. Oh, I'm sorry, did you expect a freaking continental breakfast? Am I being a bad hostess? If you were in this predicament, wouldn't your number one goal be to get out of the house of the girl who had to escort you home because you had gotten so wasted you couldn't walk?

No big deal for this fella, though. As I stood in the doorway, purse and keys in hand, he pulled off the covers and revealed that he was stark naked. Apparently, he was going commando the night before, hence the pajama jeans. I turned around and walked toward the front door, he trailed behind me, and I barely gave him enough time to put his shoes on before I pushed him out the door. After a silent drive to his car, I think he finally perceived my highly annoyed state. I just wanted him to be gone, out, away.

Not a single "thank you" was uttered. Not a single "I'm sorry" or "I feel bad"... nope. He just got out of my car, not a single word, and I never heard from him again.

Then I saw his face pop up with this article in my newsfeed today and read the accusations of extortion, murder for hire, and masterminding one of the most sophisticated drug operations in the world. Seriously?! Y'all, I went on a(n awful) date with a drug lord.


Ross Ulbricht of Silk Road
Ross Ulbricht was arrested this week on suspicion of operating a web-based drug ring that also provided false documents, hacker services, hitmen and firearms. Photo courtesy of Youtube