Ok Stupid: The Perils Of Online Dating

Sometime over the summer, I became obsessed with websites devoted to making fun of online dating. I avidly read sites like the wonderful, now-defunct OKCEnemies and spent an embarrassing amount of time scrolling through other people's private messages and dick pics. These websites showcased the rude, the sleazy, the banal, and the merely irritating. They were aggregators for the worst of the worst, and I found them anthropologically fascinating as screengrabs of the underbelly of Internet culture. This is how men who have grown up primarily online interact with women they are trying to impress, I thought. This is what Reddit has wrought.

One day, I found a site I'd never seen before. It was a collection of introductory letters written by one man to many different women on OkCupid — letters that had never been answered. The author had a large vocabulary, and he even knew how to punctuate. Be still, my heart. (This is how low my bar had gotten.) I was impressed with his efforts and charmed by his style, so I filled out the online contact form: "If I ever got a message this adorable on OkC, I would have responded immediately. My loss."

About an hour later, I got a response. His email address included his full name. Naturally, I googled him.

My search turned up a video of an attractive young man with luxurious hair and expressive hand gestures doing stand-up comedy in a Brooklyn bar. When asked, he admitted that this was, in fact, he. Rapid-fire email communication ensued. I had no idea who this guy was or where he lived, but his words seduced me.

I sent him a deliberately provocative headshot where it was quite obvious I didn't have a shirt on. "Is that your real eye color?" he wrote back. "No Photoshop?"

"You were looking at my eyes?" I teased him.

The next few days became a frenzy of emailing, hitting the refresh button over and over again. We spent every spare moment talking to each other, trying to make each other laugh. We stayed up til four a.m. talking on Skype, grinning nervously, unsure of what to say. "You're real," he said. I nodded.

I don't remember which of us suggested meeting in person first. "I looked up plane tickets to New York... Is that too scary?" I asked.

“How soon can you be here?" he said.

A bunch of negotiation followed, and when we eventually found ourselves in the same place, it seemed perfect. We finished each other's sentences and spent a whole day in our pajamas. It was the most comfortable thing I'd ever experienced.

Sure, we were both a little gun-shy. I was just out of a serious long-term relationship, and he hadn't dated anyone in four years; neither of us were looking for anything serious. He claimed to have built a wall around his heart, and I wanted some time to recuperate. Instead, what we got was the sort of serious emotion that punches you in the chest until the wall falls down.

In New York, he kissed me on the sidewalk outside Penn Station. I am not the kind of person that says they love someone 10 days in, and neither was he. Yet we found ourselves talking about living together someday, tentatively pH testing the future. He introduced me to his friends, then took me for waffles at a 100-year-old diner in Bay Ridge. As I left his apartment to catch a bus back to Montreal, I started to fish in my bag for the keys he'd given me, and he stopped me. "Keep them," he said.

Things were going well, but I had a sinking feeling that they couldn't stay that way forever. He hated not only talking about feelings, but also having them and prided himself on remaining aloof and distant from everyone...especially his girlfriends. His friends were all dudes, the kind of jocular comic guys that eschew self-awareness in favor of baseball caps and punch each other in the testicles to say hello. He once confessed, proudly, that he had no self-awareness at all — and that he didn't even know that until someone else pointed it out to him. I thought of myself as the big exception to the rule, the lucky girl who could make him commit.

When it happened, it happened big. After a week of our usual texts and foolish grinning at each other on Skype, he became more withdrawn. Finally, I asked him what was up. He asked if we could talk. As soon as I heard his voice on the phone, I knew. He was about to turn and run. "I thought I could do this, but I can't. Long distance is too hard."

I'd gotten so invested so fast, in a way that I'd never done before in my life. And, so had he, which was part of the problem. If we'd dated for longer, we probably would have fought, drifted apart, and thought of each other with a warm haze every now and then. Since we split at the height of our honeymoon period, we drowned each other with unhealthy behavior: late-night mournful sexting, joke tweets, the occasional prolonged email exchange. Eventually it petered out, but not until after I spent more time crushed in a miserable wringer of heartache than I ever had dating him in the first place.

Eventually, I realized I'd dodged a bullet. He'd told me over and over again that he didn't understand how I'd gotten past his defenses, that he liked his life much better before he met me, when things were safer. Pro tip, ladies: If you're dating a guy who says he liked his life better without you, don't keep dating him. It's not romantic. It's masochistic.

I went back to his website once, long after the relationship ended, and read the letters that had once so captivated me. They were crass and made fun of the women he contacted for not having a "sense of humor." In short, he was just like almost every other guy online. Nobody can predict what might happen in the unexplored, unexplained wilds of the Internet. But, the last thing I expected was to have a love affair that turned me upside down and made me into a person I never thought I'd be: Someone who couldn't see through a bullshit facade when they saw it.