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I Trolled Strangers on Craigslist and Learned About Human Connection

For the sake of art, I explored why our internet reactions don’t need truth or reality to run wild.
From 'Portraits of Brief Encounters.' Photo by Daniel de Amaral

In describing the bachelor suite sublet, I am fair. The apartment has high ceilings, a balcony, clawfoot bathtub, it’s just blocks away from Commercial Drive Skytrain Station––central to all amenities. But I level with the reader: it does get loud. Traffic’s consistent screech of acceleration and deceleration, the hollering of folks moving up and down Broadway, always with something unintelligible to yell into the busy night air. It can be a lot. Even with the balcony door closed the sound is there, muffled. Like riding the bus with your headphones in––you’ll still catch uncomfortable snippets of stranger’s conversations between the trumpets, guitars, synths or whatever it is your particular Music Streaming Service is feeding you.


That’s what I say in my Craigslist Apts/Housing for Rent post. I want the ad to include the flaws of the suite in order to be forthcoming, sincere, genuine––so that when someone reads it they don’t feel like they’re being put on. Right up until the moment when I want them to, which happens when I mention offhandedly that, yeah, occasionally the floor does become lava. That’s when sincerity meets the absurd and the already tenuous belief one has in the validity of an anonymous online posting is tested. Was that a typo? Does the place have lava rock tile? Some readers will immediately close the tab, having no time for my BS, but others continue, eventually running into this:

“The apartment comes fully furnished and I’ve set the furniture up in such a way that when the floor does become lava, you can easily jump from couch to coffee table to office chair, etc. to reach all areas of the apartment without being reduced to ash.”

Then it’s clear that the post is fiction. Or it should be. At least that’s how I designed it. An instance of lighthearted trolling. Instance one of fifteen. I’d scattered fourteen more of these throughout Vancouver’s Craigslist page, in all categories, in the name of art. The premise was simple: write fictionalized Craigslist ads, have local artists create a piece inspired by them and put their work up in a gallery space alongside a screen that displayed the actual anonymous responses those ads elicited from people on the world’s most popular classifieds website.


But beyond watching dogs confusedly serpentine across parks in anticipation of a ball that would never land, one I pretended to throw, I had no real experience with trolling. Especially online and with humans. Because humans are unpredictable, complex, smelly creatures, and when given the safety of anonymity that Craigslist provides they will decry, denounce, uplift, engage, solicit, and offer a range of emotional reactions that are hard to prepare for. The bachelor suite sublet ad? It received over one-hundred replies. Most in the vein of this one:

“Despite my concerns about the lava, I would like to come and view the suite for rent if it is still available.”

And that’s where my “lighthearted trolling” met reality. Vancouver is in the middle of an historic housing crisis. People are desperate. They’ll wade through my stupidity if there’s even an inkling of potential to find a reasonably affordable place to live. It only took 24 hours to amass those hundred earnest responses. Some of them even coming from the email addresses of friends. I deleted the post shortly after.

In another ad placed in the “Barter” section, I played a man who explains he’s inherited a beautiful mahogany dining table from his mother, detailing a strange, sad upbringing where all this guy had ever wanted since he was a child was a dog, so now he’s looking to trade this table for a pooch. It’s a bizarre piece which asks a lot of the reader. Will they even believe it? Will they feel compassion for the man? Would someone actually trade a dog for a table? There was only one response to this post. Someone with a kind heart, gently, courteously let this fabricated man know that they can just go to the “Pet” section of craigslist, “lots of free ones [there]… you can probably keep your table :)”


That someone took the time to respond, to help, is heartening. The ability to shield one’s identity on the Internet usually leads to cruelty and lasciviousness, not kindness. But yeah, don’t worry, that’s still there. In a story posted in the “Missed Connections” category, I describe a particularly stupid and silly one-night stand, which like most quality MCs, makes multiple references to The Exorcist. The only thing that genders the author is that it’s posted in “F4M.” And despite the ad detailing an especially specific person and experience, I received nearly sixty responses. Some claimed to be the imaginary man in the story, others acknowledged it wasn’t them but still decided to proposition me for sex anyways. And the dick pics. So. Many. Unsolicited. Dick. Pics.

The first response was just a picture of an erect penis hanging clinically out of a pair of boxer briefs with the terse command: “Come downtown now. West Georgia. I can host.” That came just two-minutes after the post went live, this man and his cock.jpg waiting to pounce. One guy brazenly even sent a link to his own sextape, as if that would entice.

The responses to that ad were a small, shocking view into what I can only imagine it’s like to be a woman on the internet––the original story, again, not asking for solicitations and graphic photos from strangers in the slightest, but yet, they came and it was torrential. I felt queasy watching those emails populate my inbox in real time, notifications like red, festering boils.


But that post also received this message:

“Odd I know but you may be a sex demon as odd as that sounds! Here’s a wiki link to what I’m thinking:”

Thanks? These were the responses I was looking for. The ones where someone shared a peculiar piece of their personality that wasn’t being directed by their dick. This person thought that I, the wholly imagined person in the ad, could be a succubus and they want to let me know! That is a fascinating kind of concern.

From 'Portraits of Brief Encounters.' Photo by Daniel de Amaral

In the “Free” section I’d plopped in a story about a roll of photos taken of someone on their deathbed that were ruined by the recently deceased’s spirit being a total perv to everyone in the room––the camera being the only thing able to capture the ghost’s deviancy.

“Yes please please I want these…I’m sorry the old guy acted so silly on a serious day and ruined your last photos of him with family but I would love to see/have these!”

Here was an anonymous person interested in the niche photographic realm of degenerate phantoms. And let’s not forget the religious scholars toiling away on this site, fact checking in the name of Big J:

“To be Baptized is a sigh [sic] to the world that you have accepted Christ to be your Lord and Savour [sic]. How than [sic] do you expect to be Baptized then if you do not believe this. I am Christian and have been Baptized. Read John 3 16 God Bless.”

A story about a practical non-believer trying to cover all of their bases by getting baptized jusssssst in case the afterlife turned out to be a real destination is what prompted that scolding and Christian chest thumping. Savour the saviour!



The show itself was about embracing a certain, known-yet-unknown darkness of the internet––eating a cherry with visible rot. Not all of the cherry is brown and folding in on itself with decay, but the parts that are? They can still make you sick. And I could feel it in my gut. It was a combination of things. I regretted trolling people looking for homes but also learned about the level of desperation affecting people in Vancouver, which was eye-opening and painful. I thought I already knew how terrible the internet is toward women, but having that amount of unsolicited hard (ugh) evidence took it to a whole new level. In the process, I found our sense of reality seems more flexible in the anonymous online space. We’re creatures that thrive on connection, and we can apparently live with a little bullshit if it means getting a stranger’s attention:

“I just want to say thank you for posting this add [sic] in the way you did. Def put a smile on many people’s faces when looking for an apartment can be stressful.”

If that fake ad was relief for one person, I’m grateful. And despite all the previous personal turmoil I’ve whipped into form with weird stone fruit metaphors, I’m grateful for Craigslist. Because this show also taught me that it’s not all terrible. Not in the slightest. Even under pseudonyms people still care. It has allowed them to express themselves, to build a community, and up until recently, make a living safely.

I only learned this because the anonymity that shields the troll also provided safe space for the teacher.

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