There’s a point on lonely Friday nights, after watching about fifteen consecutive Grey’s Anatomy episodes and stalking every last person on your Facebook friends list, that you eventually find yourself strolling through the darkness that is Craigslist personals. Located between the sadness of Missed Connections and the even creepier sadness that is Casual Encounters lies the Platonic section. Click on that and you’ll find a wide variety of people looking for someone to chat/do drugs/sob deeply with.

I decide to try a little experiment: I will attempt to make as many friends as possible through whatever Internet means I can find. Armed with a few sparsely worded ads and a whole lot of cynicism, I set out into the wilderness. I put myself out there, and wait.


I’m chatting with my friend in Brighton as we both look through Craigslist ads and compare notes.

Sietske: man, w4w ads and m4m ads could not be more different

m4m: LOOKING FOR MAN TO STICK A FINGER IN MY BUTT WHILE I INSERT MY DICK INTO EVERY ORIFICE

w4w: maybe we could hang out?

me: what if I tried to meet as many people as possible through craigslist?

Sietske: you should

some of these are so sad

you should have a party for all of them

me: I’m tempted to try that

cos I am definitely not going to fuck them


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The women I speak with are mostly in their mid-twenties, usually in some sort of graduate program, and almost always from outside of Toronto. They went to school outside of Ontario and then found themselves in Toronto, alone. The men are a little more scattered. A number of them are just lonely, or bored, or horny.

Within an hour of posting an online ad looking for someone to chat with, my inbox is inundated with emails. Most of them are guys saying yes, we should totally chat, please add my email/BBM or accept my singing telegram. A few of them ask to see various body parts, and almost all of them are poorly written. One guy sends shirtless photos. Another is a single dad in his thirties. One guy states that he doesn’t want to see my body because he’s a good Christian.

I’m wading through emails at this point, basically picking and choosing potential friends based on the messages with the fewest number of spelling errors. I pick four guys, who vary from a twenty-seven-year-old with family in Japan to a MMA fighter in Scarborough to a twenty-nine-year-old who only drinks coffee from Starbucks. I try to keep conversations away from sex — try to keep things platonic — but all the guys end up trying to flirt, and failing. One asks about the weirdest place I’ve ever had sex. When I decline to comment, he says that it’s okay if I like anal; he’s cool with it.


I worry whether or not I’ll respond to someone who I find unattractive, and that’s when I realize that it might not be me who makes that call, but them. It dawns on me that maybe they would be the one to walk into the bar, see me, and leave, turning the search for a drinking buddy into the lyrics from “Personal” by Stars. I would be the one deemed too unattractive to talk to and, standing alone in my bathroom wearing only a towel, I could feel the insecurities crawling around inside, making me shiver like the cold water dripping down my bare back.


Dunbar’s number is a constant that demonstrates the average person’s friend network as predicted by the size of the average human brain. Resting at 147.8 (¬± whatever), this number was created by anthropologist Robin Dunbar, who found that there was a correlation between the size of a primate’s brain and the size of the social group surrounding it. Dunbar found that the volume of the orbitomedial prefrontal cortex of their brains was greater in his subjects who had many more interactions with people than those who kept to themselves (although causation is still being debated). Hell, studies have shown that people are more confident online, and that even updating your Facebook profile can lead to a surge in self-assurance.

I’m trying my hardest to be honest, but I’m constantly wondering if the people I’m talking to are lying. Are they really who they seem? Are they just some creepy old guy in a basement? I know that creepy old guys need love too, but I really don’t think I’m the best candidate for that. All I want is someone to go have a drink with, but so far I’m being faced with mountains of badly spelled emails, boring chat logs, and lies upon lies upon lies.


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Finally, I make contact and set some plans to meet with someone after weeks of flaking and weirdness. I meet with K. in a bar on College Street. She’s a student, dresses nicely, and seems overwhelmingly normal. I’m already mildly intimidated. She posted an ad saying that she had recently moved to the city and was looking for someone to hang out with.

We get some beer and start up the awkward small talk. She’s in grad school, doesn’t get too many chances to meet people her own age, and so on and so forth. The experience feels like a cross between a date and a job interview. I half expect one of us to pull out a notepad and jot things down: Why do you want to be my friend? What are your credentials? Are you legally allowed to be a friend in Canada?

We end up talking about missing our childhood dogs and how we Skype with them sometimes. At this point we begin to relax, but I have to go to meet up with someone else. We exchange pleasantries outside and she hops on a streetcar. For weeks afterwards I would see her name pop up on my chat list, but I’d be too nervous to talk to her. She’d already broken past all my initial walls that kept me safe online. Now I was just afraid that if I asked her to meet again, she’d say no. The rejection sucks a lot more after you’ve met face-to-face.


I find a posting on CL from a British girl traveling to Toronto. She’s in town for a little while and would like someone to give her a tour. I quickly send her back a brief email saying that I’d love to drag her around the city and show her all the non-touristy things.

We chat for a bit and she asks for a picture, and while I feel like this is a mildly uncomfortable request, I decide to go along with it. I’m trying to impress her with my wit and zaniness, trying to set myself apart from any bland Torontonians who may have contacted her, and after about twenty minutes of searching for a photo, I decide to send off a shot of me from last Halloween. I went as the Rainbow Fish (from the children’s book), and while it’s a flattering shot, I’m wearing a ton of makeup, have a cascade of curly hair on my head, and am sporting so much glitter that even the drag queens at the club thought I was pushing it. At the time, I thought the picture said “Hey! I’m quirky and creative!” but in hindsight, I realize that the picture probably just said that I’m a weirdo with too much time on their hands and a lot of make-up from MAC. I requested a picture of her, but never heard back. I’d like to think that I’m better than feeling slighted by someone whom I’ve only ever spoken to through Gmail, but I couldn’t help but feel slightly miffed at her dismissal of my attempts to impress her, no matter how misguided they were.


After a few weeks of wading through the ugly mass of text that is Craigslist, I finally give in and log on to ChatRoulette. Venturing into this site is like revisiting yourself on all of your most boring nights. Everyone is sitting in the dark, hand on chin, not really paying attention, and if you’re not completely zoned out and lonely, then you’re masturbating furiously, hoping that someone will be nice enough to help out.

I sit there for about ten minutes hitting the next button, seeing mostly bored looking guys, dicks, teenage girls, more dicks, and finally come to a stop on a guy holding a sign that reads, “THE ORACLE SAYS YOU WILL PRESS NEXT.” I take my finger off the mouse and stare at him. He eventually puts the paper down and stares back, almost unsure of what to do.

“The oracle is wrong,” I type. “I don’t know what to believe anymore.”

“A five per cent failure rate is ok,” he says. “This is just a minor setback.”

We talk for about forty minutes. He’s from Germany, married, and learning French. He starts asking me questions about my life. “We are strangers on a train,” he writes, “and we can say anything to each other and it won’t matter. We’ll never see each other again.”

I talk to some teens from Russia, a guy wearing a witch mask, and a quiet dude who ends the conversation when I ask him if he likes rap music. In the end, I skip through the feeds until I find the ones of guys jacking off into the camera, upon which I start singing show tunes and making faces at the screen. This is what my life has become: killing strangers’ boners on a Sunday night, alone in my apartment.


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A friend of mine has a slightly different take on things: “I’ll go up to guys in bars and just strike up a conversation, and they’ll be weirded out because I didn’t try to talk to them on Grindr or something beforehand. It’s fucking weird that that’s the point we’re at now where it’s way more uncomfortable to talk to someone face-to-face than it is to ask a stranger to fuck over text or through email.”

After hearing this, I get the feeling that not only am I failing to make friends this way, but I’m probably never going to get laid ever again at this rate.


I end up with a stack of emails, a few new pen pals, and a lot of missed chances. I don’t end up with any more friends than when I started; just a full inbox and an empty schedule. But sometimes, late at night, I’ll fire up the webcam, warm up my voice, and go back onto ChatRoulette. I’m not here to make friends anymore; I’m just here to wreak havoc, one erection at a time.