Virtual Cupid: Dating in the Internet Age

By Esther Tung

I’m not a middle-aged man crawling out of a painful divorce. I shower and floss every day, and the very nature of my job has me in intimate contact with strangers on a weekly basis. I don’t shave my legs, or know how to walk in heels, and the most private thing I’ll admit is that I forget to wear deodorant a little too often, but I can still look the part of a debutante on a good night. I’m even casually seeing someone I met in real life. Despite falling short of the litmus test for an online dater, I’ve been active on OKCupid for over a month, and it’s never been a secret among my real-life friends.

The underlying stigma of dating online is that if you use it, you’re likely desperate, boring, a bigot, or otherwise harbor some other fundamental personality flaw. But this perception likely stems from self-selection bias. Horror stories about creeps, pervs, and sociopaths naturally stick around the rumour mill longer and stronger, and are the ones we’re likelier to hear about. Among the 150 or so men who have messaged me so far, only a small percentage raise warning flags in their messages, whether it’s by calling me stupid and then asking me to call them anyway, or outright admitting to their flaws. As for the majority of users on OKCupid, some have social lives that are more conducive to platonic relationships than romance, but many people are new in town (read: cute European exchange students) and are looking for someone to hang out with and show them the underbelly of the city.

I chose OKCupid over the better-known Plentyoffish largely because I knew people who already had a profile. A man with whom I’ve been in a quasi-relationship for two years set up accounts with his best friend before he met me. Encouraged by both of them being legitimately charismatic, intelligent, creative types, I set up my profile. After spending a couple of weeks browsing matches, rating photos, and answering messages indiscriminately, I unearthed even more people that I knew in real life, from sweet-faced band members that I’d interviewed to distant colleagues from rival school papers. I knew they’d be able to see that I’d viewed their profile, but that initial mortification quickly melted into curiosity. Through the answers to their OKCupid questions (which are done to help the site come up with better matches for you), I was now privy to details that would never come up in actual conversation — whether they’d be horrified or turned on by getting slapped on the face during sex, whether they would teach their kids to believe in Santa, how often they masturbated — but even the novelty of that quickly wears off.

Quick gleaning of profiles showed that most men responded often to messages, while women replied either selectively, or very selectively. Granted, women get messages from at least a couple men a day, but I resisted feeling jaded about the whole experience, and replied to all messages as long as they were polite, regardless of the person’s photos or profile. Everybody’s got a great story if you’ll let them tell it. A married man once approached me for coffee. With his permission and input, his wife wanted to see another woman outside of the marriage. I declined, but mentioned that I had read The Ethical Slut, which led to a grand-scale discussion on polyamory and swinger culture. Eventually, some conversations stood out more than others, and meetings were proposed.

Over the span of a month, I met four men, and my only criterion for accepting an invitation to drinks was that we had kept up smart, sincere conversation over at least three or four exchanges. Even at this juncture, I put physical attraction on the backburner, and took it as an exercise in cultivating connections with people. It might have been an unusual approach to take in online dating, but in retrospect, such indiscrimination was central to how much I got out of the whole experience.

My first date lasted three and a half hours; my most recent one drew late into the night and clocked in at eight. I kissed one on the first date, and I have yet to even break the touch barrier with another even after third-date brunch. I’ve showed up underdressed and overdressed, too early, and too late. I’ve revealed insecurities, argued politics, and been uncool. I’m in the middle of what Cosmo calls a “boy binge”. Maybe being approached by a seemingly endless supply of good matches is what emboldened me to break pretty much every dating rule ever published under self-help, but this has serendipitously made dating the most fun it’s ever been. When you break all these rules, you realize that nobody actually knew they were rules in the first place.