DerekTheClown entered my apartment yelling as I greeted him.  “Tower!” He screamed, apparently about the high-rise I live in with my parents, who were, mercifully, not there.  He brushed past me to dump his six pack of Red Cap on my kitchen counter and proceeded to go through my closet looking for second hand finds.  He selected a black and white Urban Outfitters dress, whipped off all his clothes and shimmied it over his shoulders; he looked like Fred Flintstone.  “I love you,” he said, then he kissed me, hard.

Derek looked exactly like he did in his photos – like the most beautiful and crazy person I had ever seen.  He had wildly long hair with a beard to match, sharp blue eyes and the tanned skin of a construction worker; I had to clench my jaw to keep from gawking at his physical attractiveness.  Clearly I had gotten lucky.  Derek’s photos are what initially led me to message him, as they painted a pretty accurate picture of his perfect physique and weird lifestyle.  Among them were a picture of his hairy face taken in a dirty bathroom mirror and another of him jumping over a fire wearing a loincloth.  I continue to hear horror stories from friends who have been on dates with people whose photos are a total misrepresentation or several years old.  “Yay!”, I remember thinking.

Clearly, I’m a bit of a risk-taker when it comes to online dating, and I am (or was) more than willing to invite strangers to my house for weird drunk/naked dance parties in an effort to find love.  But really, online dating is for mentally healthy people too.

The origins of online dating depend on who you talk to; there have been various iterations and attempts to match total strangers using computer algorithms, video interviews, or phone chats since these technologies have been taken on by the sad, lonely and entrepreneurial.  But none have come as close in popularity and user count as the online dating behemoths of today like, started in 1995, now even more gargantuan thank to buyouts of smaller competitors.

Now operating in 24 countries with millions of users, is likely the first place many people go when seeking out an online dating site; its net worth is estimated in the billions.  Definitely geared towards the mainstream, is successful in being everything to everyone.  Though it’s feels a little clunky, it feels like a deliberate demonstration that online dating is no longer cutting edge – perfectly suitable to you and your suburban house and Acer computer.

Of course, all dating sites, whether they have millions of users or just a small slice of the market pie, have a certain flavour and vibe.  Colloquially, eHarmony is for old farts that want to find true love, while AshleyMadison is for people that want to cheat on their wives with someone with a name like Ashley Madison, though they’ll probably end up screwing someone named Nancy who also drives a minivan.  There are the religious sites, like ChristianMingle and JDate which are also used by the secular-minded looking for stability (with the former) or wealth (the latter).  Then there are the free sites, the most popular being PlentyOfFish and OKCupid, which are both basically a sea of horny hipsters and thugs who live at home.

The differences between these dating sites are really reflective of what their creators were trying to accomplish –  eHarmony was founded with an eye towards lowering the divorce rate, so to sign up you are forced to answer an hours worth of personality questionnaires and can only view the profiles of people with whom you are compatible.  You also have to be pretty financially committed to finding romantic harmony, with a one month subscription running at about $60 a month with discounts if you sign up for longer.  OKCupid on the other hand was started by a crew of Harvard mathematicians and is thus focused on getting their users to answer questions of varying predictive value.  For example, answering yes to “Do you like the taste of beer” is highly predictive of whether someone will have sex on the first date.  Ultimately though, all of these sites are faced with the same problem: how to facilitate meetings between strangers.

I first heard about internet dating in a socially acceptable context back in 2011 when a good friend of mine introduced me to OKCupid.  She was using it to reach out to a demographic that was new to her – men.  Before her introduction I pretty much thought internet dating was for sad sacks looking “the one” because they were too weird for the real world, like WOWers, people with facial deformities, Asperger’s, or my Grade 12 World History teacher who unfortunately resembled a human mole, who I found on LavaLife.  When I first signed up and carefully created/curated my profile, it was like I had just discovered Facebook.  I was struck by the sheer number of “normal” people out there with pets and mothers and jobs who were waiting for me to click onto their profiles or send them a stupid message.  I was immediately hooked and began going on date after date after date – sometimes more than once in a night.

Of course, online dating isn’t all fun and fucks, sometimes people get raped and murdered.  Carole Markin famously sued to begin doing background checks on its users after she was brutally raped by a registered sex offender on their second date.  Even more notorious, the so-called Craigslist Killer (aka medical student Philip Markoff) was accused of three armed robberies and a murder, all of the victims reportedly having made contact with him via Craigslist personal ads.  What is clear about these terrible scenarios however is that they could have occurred in the context of “regular” dating too.  Just like in the non-virtual world, online dating requires some reliance on gut-feelings and best practices.  It’s probably not a good idea to go home with a stranger or invite them over for a first date.  In practice though, I have a hard time taking my own advice.

After Derek was settled into my dress and couch we drank a ton of beer, listened to music, made out and chatted a little bit.  This date was an after party for both of us, as he was coming from a concert and I had just been out on another date.  At some point we had to sleep so we took to my tiny tower-sized twin bed and cuddled until we drifted off.  The next day we explored Scarborough, shopping for thrift clothing and jewelry, talked about getting married and ate at Subway – Derek loved Subway, I think ironically but maybe not.  I found his stash of approximately 20 parking tickets.  Derek parked where he wanted to.  In hindsight I was totally falling for him but I kept it together reasonably well that first 24 hours and avoided acting like an obsessive teenager

I had promised that first date from the previous night that I would see him again, so later in the day I made up some story about a dinner party I had to go to and got Derek to drive me to his house.  (I literally will always wonder if this had karmic implications on the trajectory of my relationship with Derek, but more on that later.)  We tongued each other goodbye and he honked several times as I made my way up to the door of this other guy’s basement apartment.  At that point I knew I couldn’t give less than one shit about other dude and was excited for when I could see Derek again.

Derek and I dated for a whirlwind seven weeks of trips to Toronto Island, tours of his hometown, too-hip concerts and countless tall-cans of Old Milwaukee.  Finally, he dumped me, leaving me a total emotional mess.

Ultimately my experience with Derek taught me that it is actually possible to find love on the internet.  Though it didn’t work out between us, finding Derek on OKCupid refined my tastes, raised my standards and exposed me to one of the very best people in the world.  I am convinced that there is more of the same out there.  While I sometimes get frustrated after a few hours of progressive drunken but still boring conversation, I find some shallow comfort in the fact that there is always going to be another internet man rating me 5 stars.



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