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Weird Tales From My Year On Gay Dating Apps

Dating can be scary, and online dating especially so. Prepare yourself by laughing at other people's misfortunes.

Illustrations by Claire Milbrath.

​After breaking up with a boyfriend in 2011, I wanted to explore online dating and give being single in Toronto a shot before jumping into anything serious. Unfortunately for me, I soon realized that the gay dating world came with its own set of rules, most of which are pretty weird and somewhat racist. Race, body shaming, identity politics, and masculinity seemed to come up a lot and eventually I just said "fuck it" and deleted every dating site I was on. I needed a break. I needed to hear something other than "looking for whites only" or "straight-acting only." It got to a point where I felt shitty about wanting to get laid and needed give the online thing a rest.

In 2013 I came out of "online dating retirement" and decided I wanted to explore it again. Every so often I'd hear my friends gush about all the great dates and hot sex they were having on Grindr and Scruff. It took a lot of convincing, but I decided to give a few of these apps a shot. I downloaded both Grindr and Scruff and immediately starting messaging people. Throughout that year, there were a few really nice conversations that didn't really go anywhere, the occasional good ass and/or dick pics, and an older couple in their 80s that always messaged me in Spanish. But aside from that, the string of weird encounters just got worse every time, and in January, I finally decided to delete all the apps and have sworn off online dating and hookups for good. But, below, you'll find three stories that I'll probably never forget.

Picture Tag Gone Wrong
Around Thanksgiving last year I got a message from an Irish guy visiting the city for a few weeks. I chatted him up about all things Ireland and told him about a trip I was planning for spring 2016. The vibe was friendly for the first few days, and then he wanted to see some pics, which I was more than willing to share. I sent a face pic to start and he sent one back. He was a bald, rugged, bearded man with green eyes. Suffice to say the dude was really hot and definitely checked off a few boxes in the "my type" department.

We talked for a week and he eventually asked me if I had a dick pic. I sent the most recent one and waited for him to send something back. Two hours later he sends a pic, but it's not of a body part or another sexy face pic, it's a picture of him and his sister with the caption "hot pic." I wasn't sure if this was a mistake or a joke, but I decided to just brush it off and send another dick pic. He then responded with a picture of him smiling with his grandmother, saying nothing else afterwards. Two days later he messaged me to ask what I was doing. I told him I was just enjoying my day off and asked him what he had planned for the day. He then sends a picture of his spread asshole dripping with cum, a picture of him and his dog, and then a picture of him having family dinner, again saying nothing else. At this point, I wasn't even mad or upset. The dude clearly wasn't serious. That or he had a fucked up sense of humor. As funny as the whole thing was, I decided to stop communicating with him entirely. I often wonder what a dripping asshole, playing with your dog, and eating dinner with your family could be code for, but I guess I'll ever know.

"Racial Play"
I messaged a guy after work one day just to see if he'd reply. He messaged me back and said he comes to Toronto for work every day and wondered if we could hook up later that evening. I told him we should drink a few beers at my place and see where it goes. He came over around 10:30 PM, and made a few weird comments about the beer we were drinking, calling it "hipster beer." That sort of turned me off, but I decided not to read too much into it. I wasn't expecting things to heat up after the weird beer comment, but after six beers we just went for it and started making out. Before things escalated, he stopped me and said he needed to tell me something. I remember being puzzled and asking what was wrong. He told me he was into a few kinks, but didn't know how to talk about them. Fetish is always an awkward subject for people, but I assured him I wasn't easily weirded out. He looked extremely flustered and scared to say it, but after about five minutes of circling around the big confession, he sheepishly blurted out that he was into "racial play."

I kind of giggled and then looked at him again. At that moment I realized he was being serious and took a deep breath because, as a black man and a human being, the whole thing had just thrown me off. Solely based on curiosity, I asked him exactly what this type of roleplay scene would entail. It scared me to imagine where this conversation was going to go, but I still couldn't quite process what I just heard. I've done some weird shit, but this whole thing was fucked up and I didn't understand what turned him on about it exactly. He asked me if I was mad that he was into that. I told him no because I actually wasn't pissed at all. After having another beer he got into the finer details of how a "racial play" scene would go down.

According to him, a play scene would involve me in a cage, getting choked with his dick, while he spits on me and calls me nigger a few times. He assured me that while it was a lot to handle, it was actually a pretty popular fetish. It's just something that nobody talks about. I looked at him, extremely puzzled after that statement. He stood, confident in his belief that was an acceptable thing to get off to, and it took a minute for me to figure out the best way to respond to this very unsettling fetish. Wanting to end this interaction on a peaceful note, I told him that while I respect his honesty, the thought of a man getting off to calling me racial slurs and performing violent sex acts on me was enough to make me want to commit murder.

When I said that he laughed it off, but once he saw the expression on my face, I could tell he knew it was probably in his best interest to call it a night. After he left I Googled racial play and found a lot of crazy shit, most of which I wish I could unsee. There are certain thoughts and images that linger in the subconscious and lead us to the fetishes we have. I think most things are fair game, but if me picking cotton gets you horny, there probably won't be a second date.​

Runaway Cucumber
One of the first guys I met on Grindr was a university student who had just moved to Toronto for school. During our first hangout we drank a few beers and talked about Toronto, which was a nice change from the usual in-and-out hook up. We immediately hit it off and it turned into an ongoing thing. We met up for sex about twice a month for a couple of months. It was really low-key, which has awesome because I wasn't after anything serious at the time.

One night he came over and dropped a bomb on me. Apparently he had a girlfriend, which was news to me. He said he wasn't gay—he just met up with guys because his girlfriend wasn't into anal play. This all seemed messy and complicated, so I told him we should cool it on the sex until he and his girlfriend had a serious conversation. It would be one thing if they were in an open relationship, but it seemed more like their lack of communication had led to him sneaking out to get fucked by guys behind her back. It just didn't seem healthy for me to continue sleeping with him if that was the case.

He texted me out of the blue three months later, asking if we could meet. I had my reservations about it, but I decided to let him stop by and get an update on what was going on with him and his situation. He came over and immediately went for my crotch, but before I could let it go any further, I needed to ask what the status of his relationship was. Apparently he had broken up with his girlfriend and was exclusively fucking guys. The way he talked about these new relationships was very strange. He maintained that he was still straight, but just really loved bottoming now and couldn't get enough.

We proceeded to play around a bit and eventually I was fucking him. I don't know if fate was punishing me for allowing my thirst to blind me from the obvious mess of a situation this was, but ten minutes into it I'd felt something wet go down my leg. Lets just say that he wasn't ready to bottom and by the time I stopped the evidence of that was all over my bed.

When you're having butt sex, there's always the slight possibility of a little shit, but this was literally a shit storm. He felt really bad and I didn't want to make a big deal about it, so I said we should just shower and call it a night. I let him go first so I could throw away the sheets and after he got out I went in to get myself cleaned up. When I walked out of the shower, what I saw him doing brought new meaning to the phrase "by any means necessary." I stood quietly by the door and watched as he began squatting down on a cucumber from my fridge, trying to fuck himself with it. He was jerking off and heavily breathing as he attempted to fit the entire cucumber up his ass.

After a minute or so, I purposely slammed the washroom door and he freaked out when he saw me standing there. He could tell I was pissed and he kept trying to avoid eye contact. I asked him what he was doing still naked, which left him stuttering as he tried to make up a good excuse. I snatched the cucumber out of his hand and asked him to put on his clothes while I finished getting dressed in the bathroom. After we were both dressed I walked him out of my apartment and told him he shouldn't contact me again. I didn't want to be an asshole, but between his first lie about the girlfriend and the shit-stained bed I had to throw out, I felt like the universe was trying to tell me this needed to end.

To make matters worse, when I went back into the house, I checked the fridge and the fucking cucumber was gone. I was short an ingredient for my next lunch. I ordered a new bed and went to do groceries the next day. Thank you universe! I definitely got the message.