Online Dating: The Funny, The Weird, and The Just Plain AWFUL

Admit it, we’ve all done it. The constant deliberation of “is this photo cute?”, “should I even put a bio?” or “it’s been 10 minutes and he hasn’t messaged me, should I block him?”. We continue to put ourselves in these situations where we spend hours upon hours finding someone to meet up with – but are mostly left with jagged conversations and the occasional flakey catfish. But every so often, the lucky ones manage to snag a date with their ideal guy or gal…or so they think. We’ve searched within the vast network of Toronto millennials and found you some of Tinder, Bumble and Grindr’s best dating quirks, mishaps, and nightmares – enjoy.


I don’t normally go on tinder, but something compelled me to give it a shot that day. I ended up matching with this guy who seemed pretty nice over text, and easy on the eyes. So of course when he asked me out I was more than down. To be honest, I wasn’t looking for anything serious, nor was I looking to hookup – kind of just wanted to meet someone new. Anyways, we picked me up in his BMW which already right there should have been a red flag. He told me we’d go out for ice cream which I mean, it was hot as s*** outside, and I was on my period so he was definitely speaking my language. The conversation was pretty light 10 minutes into the drive, casually asking questions about each other, you know the normal stuff. I noticed while we were driving through the core he was heading for the Spadina exit to the Gardnier Expressway – I honestly didn’t think that’s where he was going. That’s where he was going. I asked him where exactly the ice cream shop was and he said that it wasn’t far and taking the Gardnier would be quicker. Well that supposed fast track route turned into him driving me 2 hours to Niagara Falls. I didn’t have the heart to tell him to turn around – mostly cause he took me 2 hours from my home and I needed a ride back. I honestly don’t think I would have been as mad as I was if the bloody ice cream shop wasn’t CLOSED. The worst part about the whole experience is that during the drive THERE and BACK, he played his own mixtape…on repeat…and proceeded to gloat about his “accomplishments”, I’m sorry and your name was? I thought we were going for ice cream not a f****** road trip. Haven’t used Tinder since.


I am a tinder hoe. I use tinder and bumble on a daily basis and there was one night where I might have gone too far. I was feeling extra bored since running out of tinder swipes and potential matches so I ended up getting Tinder Premium – not my proudest moment. Before I continue though I’ll lay down some background information. My job right now is an HR consultant for a firm – so part of my job is companies will hire me on to do recruiting for them. More than once I have found girls on tinder that I ended up sourcing on LinkedIn. But before that I talk up these girls on Tinder with the classic winky faces and eggplant emojis – real fckboi antics. Now while I’m trying to recruit these girls I’m also pretending like I know nothing of their background (whatever they told me on tinder), and try to be “professional”. A few days after I got premium I ended up interviewing this one girl whom I met on tinder (praying she didn’t recognize me). She honestly had all the qualifications and seemed like a good candidate for the job. So I then asked her position related questions like “what makes you a good candidate” and “how is your social communication skills”. Her response totally through me off. She said that she likes to enjoy different applications that allow her to expand her reach with specific demographics – more specifically the opposite gender. I kept my head down during the rest of the interview. Long story short though, she got the job and I made a lot of money from it – so a happy ending?

TWINNING – Boy. 26. Bumble

This happened about a year ago back in late November. When winter comes around (especially in Canada) everyone wants someone to cuddle by the fire and enjoy a nice glass of wine. Maybe I was hoping for too much with this guy. This guy I matched with on bumble invited me over one night to hangout but because I’m paranoid AF I asked him to hangout during the day just to see if we would get along at the very least. Turns out he was a pretty nice guy! We had a very casual date grabbing coffee and walking in the park. So when he brought up the idea of coming over again, I couldn’t refuse. Later that night I went over to his house – mind you a I had a couple glasses before going because I was still nervous. We talked, made out, talked some more then shifted over to the bedroom where things got heated. One thing led to another and well you can pretty much figure out what happened. The next morning (he was kind enough to let me sleep over) I was getting ready to head back home, I headed into the living room and saw “Dave” – let’s call him. Just casually making breakfast, but I knew I wasn’t crazy and literally saw him still sleeping in the bed when I left the bedroom. I was going to go back and check but not even 2 minutes after, Dave left the bedroom. Both guys standing next to each other in the kitchen, looking exactly the same, staring directly at me. Turns out I didn’t actually sleep with Dave but instead his TWIN brother “Alex”. They knew I was in a bit of a shock so they explained that the whole switch up was a joke they pull on guys they hookup with – hilarious. Aside from that experience they are actually pretty nice guys and I ended up dating Dave up until now. Sometimes I wonder if I’m really with Dave or with Alex – either works for me #twinning.

LET ME PAINT YOU – Girl. 22. Bumble

I’m on bumble and tinder pretty often – I guess I just got lazy of going out and meeting people. I ended up matching with this guy on bumble who was really hot – abs and all. Part of me at the time thought it was too good to be true and that he was probably a catfish. I ended up meeting him anyway. When he showed up at my door he was just like the pictures – toned, amazing jawline, wavy hair and a winning smile. His plans were to take me back to his place for some dinner – I was too lazy to cook my own so obviously I didn’t mind – a girl’s gotta eat. During the car ride he kept complimenting me on EVERYTHING. Don’t get me wrong, I’m not one of those pretentious girls that can’t take a compliment or thinks I’m too good for one, but this was a little excessive. I’d say most of the conversation on the way to his house was him telling me how good I looked in the lighting. Dude it was dark outside, the only lighting I was getting was from the lamp posts on the roadways. Just before we got to his house, we got into the conversation about past relationships – mine in particular (his choice). He then offered me to get a picture of his abs to send to my ex, which made me laugh because I thought it was a joke – it wasn’t a joke. Once we got in his house he sat me right at the kitchen table. Now my assumption was that he was going to cook then and there – he actually made it beforehand which was nice (mostly because I was starving). Apparently the pasta he made has been sitting for a couple hours while he was getting ready to meet me. The pasta was served cold – which I mean, again not a huge deal since I was starving. Not even 5 minutes into the pasta though he interrupts me to watch the movie with him. The movie of choice you ask? Edward Scissorhands – turns out it’s his favourite. The best (worst) part of the movie was when he tried to make-out with me during the most AWKWARD scene (like when Edward tries to be fresh with his lady love, but ends up cutting her instead). Then right before the movie ends he leans in and whispers into my ear and says “let me paint you”. You can pretty much piece together what I did next (no he didn’t paint me).

GRADE A WEINER – Boy. 23. Grindr

A friend of mine actually loves going on Grindr. He’ll going on during family functions, classes, really wherever. I always know when he’s on because I’ll hear that iconic *bloop* sound. One day we were talking about online dating and how he’s taking this feminist class as an elective. He told me that guys on Grindr have no shame and will constantly send unsolicited dick pics to him all the time. He actually had a cache of over 100 of them. How do online dating the feminist class tie in you ask? Well he actually used the pictures as a part of the final class project where he talked about the problems with sexual gratification vs legitimate intimacy. Long story short he got 100% on the assignment – and his professor saw all the pictures…all of them.

The online dating world is a very, very odd place.