Our Staff Shares Their Cringiest Real-Life Dating *Horror* Stories

Faceless couple hiding faces behind carved pumpkins in autumn forest — Pexels

Ah, love. Most of us want it, but — with so many head-shaking opportunities for cringey, awkward and confusing dating situations — putting your heart on the line can be a bit of a bone-chilling experience. In honour of spooky season, and to help take the sting out of those dating fails, our staff rounded up some of our own (anonymous, of course) dating horror stories.

A couple stands in front on neon lights at night — Pexels

Next time, use a spoon

After getting out of a long relationship, I ran into a person who I had gone to kindergarten with but had completely lost touch with over the years. He asked for my number and called to invite me to a Halloween party the next night. In my mind, the story of reconnecting with this man who I shared elementary school pictures with felt like kismet. Meant to be.

I also stained his friend’s cream-coloured couch with splotches of blood red.

Things were going well at the party, but I was nervous. He offered to get me a drink, and brought me a strong-pour vodka and water, which was what the other girls at the party were apparently drinking, but which was disgusting. Not wanting to seem uncool, I had a brilliant idea: in the bottom of my purse there was a sachet of berry-flavoured Crystal Light drink mix. I would simply add that and sip my drink like I could hang. The only problem? Me and this man were sitting cuddled up on a couch far from the kitchen, and I was scared to get up or say anything. So I poured the flavour onto my drink and…. blew on it to mix it.

Instead of adding flavour to the drink, I instantly dyed his white (knight? I think?) costume red. Not only that, but I also stained his friend’s cream-coloured couch with splotches of blood red. Mortified, I instantly started crying. I offered his friend to pay to clean the couch, but she just looked at me with disgust. My date told me he was tired (it was like 8PM) and said I should leave, which I did. Alone.

Hopefully, there’s no such thing as a “kindergarten reunion” in my future. And, I’ll never drink Crystal Light again. — Anonymous

Swimming with the fishes?

I’m an animal lover through and through, so the idea of going on a date to the aquarium sounded perfect – that was until I got there.

After a long commute to the Ripley’s Aquarium, my date met me at the front doors only to tell me he didn’t want to do it anymore. So, despite creating this “romantic” narrative of a night under the sea, I had to walk across the entire downtown core in the freezing cold to our next spot.

Would you believe we went for sushi right after? This man wanted to take me to see LIVE FISH and then go and eat DEAD ONES right after. That’s some Silence of the Lambs sh**, I’m telling ya. — Anonymous

True horror: don’t forget to double-check the recipient

When I was in high school, I was doing my NLS, which is the course you need to pass to be a lifeguard. There was this super cute guy in my course. Tall, brown hair, blue eyes and his name was “Alex,” which for some reason I thought was very hot. We would talk in our course, but that was about it. But, because I was a drama queen in high school, I told some of my friends about him, and was certain we were going to fall in love.

He’s not photogenic, hot in person though.

I was messaging my friend about him on Facebook one day while I was in my study hall period. She asked if I could send her a photo of him. Obviously, I was more than happy to! I went to his profile, screenshotted his profile picture and sent it with the message “He’s not photogenic, hot in person though.” Unfortunately for me… I sent that to him.

As soon as I realized what I had done, I jumped out of my seat and screamed. Everyone in the class looked at me and I ran out of the room. I ran to the library where I enlisted the help of another friend who followed up with the message “Jk he’s very hot. Love you bye.” Because apparently, she thought that was going to make it better…

I immediately started doing damage control and posted a status saying “TO ANYONE WHO GOT WEIRD MESSAGES FROM ME OVER THE LAST FEW HOURS IM SO SORRY! LESSON LEARNED: HAVE A PASSCODE ON YOUR PHONE.” Which of course… fooled no one.

That Sunday, I unfortunately had to see Alex at my final lifeguard course. It was the day of our exam. I passed all the physical tests but then we got put in groups to do our situation tests. Guess who was in my group? Alex. I was so freaked out and distracted, I unfortunately did not pass the exam. But I did get a great story. — Anonymous

A case for a ‘friendly’ ghost?

Ghosting is never cool, so in an effort to be a mature adult, I always make sure I end things with dates in a text or call that kindly explains that I’m moving on. The last guy I dated took it graciously and peaced out — or so I thought.

A couple weeks later, I got a text from him asking if I was sure of my decision. I texted back: Yes, I was sure, but we could still be friends! I didn’t expect what came next. He wanted to do a deep dive into why I wasn’t interested in him, trying to convince me that I was confused and even calling me calculated for even going on any dates with him to begin with. But dating in Toronto, could I expect anything else? — Anonymous

A bloody mess

I don’t have one specific horror story — I have a series of small instances with one particular person, that – for a second – made me wonder if I’m the drama (spoiler alert: I was not).

I talked to this guy off a dating app for a couple weeks and he was clinging to me for dear life. From making jokes about meeting my parents, constantly comparing me to his ex-girlfriend, calling me five times in a row when I didn’t pick up, to gaslighting me over something as small as telling me he’d done things for me that he never had, those few weeks felt like a lifetime.

One time I went for a Tesla test drive, and when I told him about it, he had the audacity to tell me I couldn’t ever afford it. When I told him that I actually could, he wanted proof.

On our second “date,” he took me to an Airbnb after dinner (worry not, my best friends had my location on), and when I told him I wasn’t that type of person and wanted to know him longer than two weeks before he even thought of it, he got offended because he’d “spent the money and time booking the place.”

The final straw was the day he wanted me to drive two hours to his city – I woke up that day with excruciating cramps, and no matter how hard I tried to get up and get ready, I could barely stand. I told him, and he left me on read and proceeded to post stories of himself out and about, so the next day I did what any sensible person would do, and said I hope you know how to handle your future wife and daughter when they get their periods, because that s**t is not fun. And then blocked him. — Anonymous

It’s simple: at least order some fries

It was our first date, and he took me to a Tim Hortons/Wendy’s parking lot. Now this may sound like a cute, late-night fast-food run but when we got there, he proceeded to park next to 8 different cars revving up their engines and comparing car parts. No fries, just cars. That was the date. I walked home. — Anonymous

Magic tricks on VHS: a tale of red flags

My first teenage job was a thrilling opportunity to meet people my age outside of my sheltered school experience. Having grown up with the social prowess of a stump when it came to the opposite sex, I was thrilled to be able to flirt and be a new person outside of who I was at school. No one had to know how awkward I was, or that I had never dated. My workplace was teaming with equally awkward teens, many of whom enjoyed the late shifts our workplace allowed, and little adult supervision.

The second I walked through the door and saw the tinfoil, I knew I had to leave

One evening I agreed to go over to a guy’s house to hang out after work (was this a date?!). As the naive teen I was, I assumed this would mean hanging in the basement while the parents were upstairs and maybe some groping at an inappropriate moment.

After a long walk to a part of town I hadn’t been to before (red flag #1), I walked into an apartment with the windows tin-foiled over and I THINK someone hiding on the balcony (red flag #2 and #3).

I was then asked to watch videos (on VHS no less) of this person performing magic tricks (red flag #4).

The second I walked through the door and saw the tinfoil, I knew I had to leave as quickly as I could for my own safety. I endured two videos, an attempted kiss and then said that my brothers would be out looking for me if I stayed out much later (they were, in fact, not out looking for me).

He reluctantly agreed to walk me home, but not without a suspicious trip to the balcony and a furtive glance at the door (red flag #5 and #6).

I figured I had one chance to discourage him from ever speaking to me again, so I repeatedly called him by the wrong name, answered an exceptionally well-timed call from my brother asking me to grab chips, and then had them take me to a different house so that he wouldn’t know where I lived. Teenage workplace dynamics are complicated enough, but add a trip to a sketchy apartment, magic tricks and lots of acne, and it was enough to make me request that I never be on the same shift as them again. I also casually warned the other girls at work. Since then, I’ve implemented several safety checks before going anywhere with a man. — Anonymous

A pool party — without a splash

Once I went out with a guy who wanted to take me to play pool. I was hesitant to go because I wasn’t that into him, but my friends convinced me I should give him a chance and get to know him, so I decided there was no harm in going.

He took me to a bar to play pool, and I assumed I’d get a classic rom-com moment where he’d put his arms around me and teach me how to shoot the balls properly. Sadly, this was not the case. Instead of teaching me, he was critiquing me the whole time (I had never played before, so I wasn’t very good, obviously) and clearly wasn’t impressed. At the end of it, I assumed we’d never see each other again because I thought it was clear neither of us had fun, but then he asked me out after that.

Needless to say, I did not go — and I haven’t touched a cue stick since. — Anonymous

Don’t date in your own neighbourhood

Fresh out of an (extremely dramatic) four-year-long on-and-off-again relationship, my roommate had challenged me to go on a date with someone new every day for a week. Lots of horror stories came out of those seven days, but the worst one took place when I met up with a girl I had been talking to on a dating app at a bar around the corner from me. For 30 minutes straight she talked to me about her ex before asking me if I minded if she vaped at the table – which was inside, in the middle of winter (spoiler alert: I minded). I told her that I’d rather she didn’t and she looked me in the eye defiantly as she pulled out her vape and took some lengthy drags.

I had to meet a friend that night, so I had an easy out and made my exit. I thought that would be the end of things, but a week later it was Valentine’s Day, and out of nowhere I woke up to a text from her that read “happy day of love.”

The worst part? She also lives in my neighbourhood and every time she sees me, she yells my name from afar on repeat until I walk over to have an awkward conversation. — Anonymous

…And definitely don’t date in your own building

It all started with a parking spot. My much-older boyfriend broke up with me and left me, still a student, to handle the payments on our apartment, while he took the car. Heartbroken and house poor, I decided to rent out the parking spot that came with our unit to make some extra cash. The person in the unit below me took me up on the offer, and we had several months of pleasant once-a-month cash exchanges.

Then, he sent me a different text: he and his girlfriend had broken up so he no longer needed the parking spot (ugh), but he was wondering if he could take me out to dinner, as we’d obviously always had chemistry (huh?).

Still hurt from my own breakup, I fell for the confidence boost and started “dating” this man. Weirdly, he never, ever wanted to go out anywhere. He always wanted to come to my place.

A few weeks into this confusing routine, a fire alarm went off in my building while he was over. We joined our neighbours, including the ex-girlfriend who still lived below me. My date immediately went over to her and told her that he had been “hanging out” with me to stay close to her, and that he still loved her. She was upset and creeped out. I was upset, creeped out and humiliated.

The humiliation carried on for another six months, whenever me and the ex-girlfriend had to share an elevator (never, ever meeting each other’s eye). Even worse? I never found someone else to rent that parking spot. — Anonymous

No flight plan

At this point, I think everyone knows dating in Toronto can be horrendous, but here I am trying to find the “one.” I started talking to this guy from my uni who was really into planespotting last winter. He asked me on a date to Pearson airport so he could teach me more about airplanes and stuff… in the cold.

I decided to say yes and quickly learned that probably wasn’t my best decision. With no plans in sight, when we get to Pearson, he quickly tried to get me in the back seat of his car for a “better view” — mind you, all we are doing is looking at the sky… So better view of what exactly? He’d ask a few times again and was annoyed that I didn’t want to. Thirty-plus minutes later, we grabbed food, and I headed home.

I unfollowed him later to get rid of that weird energy. — Anonymous

Animated movies will always hit different now

Back in college, I joined the student newspaper and felt like I had found my people. One person, in particular, made me feel this instant, deep connection. He was tall, handsome and knew how to write a headline. I was hooked.

Over a few weeks, we started talking every day. He asked me, via a handmade pop-up card, if I’d go on a date with him. We went ice skating under the stars. We laughed so much. He kissed me — once — very respectfully.

So, when he begged me to come over and watch his favourite movie, Toy Story 3, with him, I assumed that he a) loved me, and b) was going to move things forward in our relationship. So, despite the fact that I had actively refused to watch any animated films for many years (that’s another story), I abandoned my own wants and caved.

I sat through the whole thing and noticed that he went out of his way to sit on the opposite side of the couch. When the credits rolled, he immediately suggested that he walk me out — and told me that he wanted to only be friends but wanted to share that movie with me first.

While I didn’t speak to him for months, I did eventually get over it (we really do have a deep connection) and he was right — we are better as friends. — Anonymous

Stay out of dark alleys

Fatigued by the dating app style of essentially ordering a pizza to try to find genuine connections, I let a friend set me up. This guy was a lawyer, and my friend said he often took on pro-bono work for people who couldn’t afford legal representation. I thought that was super cool, so I was excited. My friend also told me that he thought we had a similar sense of humour.

I guess my friend thinks I am trash, because about 30 minutes into the date, this guy asked me if I wanted to “walk into a dark alley and eat his a**.”

I politely declined his generous offer. Before leaving, I made sure to “accidentally” spill my drink on the table right over the umbrella hole so it would trickle all over his dumb khakis. (Why do you need so many pockets?) — Anonymous