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Embarrassing dating stories: The incredible saga

By Anonymous, February 6 2020—

We’ve all been there — the stars cloud our eyes and our better judgement and we find ourselves on terrible or embarrassing first dates. Enjoy some mishaps from some of our contributors. 

The “Dick Whipper”:

I honestly don’t know how to start this story other than saying that Tinder is trash and has trash people on it. After having a pretty standard first date with one of my matches, I decided to entertain a second date since I thought “no harm, no foul.” Well, that was mistake number one. Along with yelling at waitstaff, the last straw was when he — unprovoked — whipped out his dick in his car and asked if I “liked what I saw” and if I would “give it a kiss.” I immediately asked him to drive me home and never spoke to him again. 

The Romantic Repetitive:

After my long-term boyfriend broke up with me, I decided to throw myself back out into the dating world to face my fears of meeting new people. Luckily, I had some pretty stellar dates. And in particular, I met this lovely guy that took me out for coffee, a walk around Prince’s Island Park and even up to the roof of a skyscraper. Even though the date was magical, it seemed a little rehearsed and there was no romantic connection — which he sensed as well. Flash forward three days, I’m sitting with a friend in the same cafe and in walks the same guy with a new girl. He made eye contact with me and quickly shuffled his date out while turning beet red. That night I received a text that said, “Didn’t realize Calgary was such a small place. Wanna go out again?” Hell no, my friend.

There was more than tea in his cup:

When I worked at the mall, I made eyes with a guy who worked at DavidsTea. If we had the same shift, I would often visit him on my break, order a cuppa and we’d talk about everything from our favourite tea blends to our personal life. This went on for a couple of months and it was super harmless since he seemed quite nice and normal. We eventually matched on a dating app and immediately set up a date. He rolled up to my house in his beaten-up SUV with my favourite DavidsTea blend brewed in a travel mug and gave me a big ol’ smile and hug — I was smitten. But soon, I started seeing cracks in his near-perfect persona and our night soon turned into the date from hell. Not only did he tell me he dealt drugs in high school — mentioning how he missed the days of making $80,000 a year — but that he still gets death threats from his previous drug lord for not paying up back in the day. He also kept pushing me to have sex with him that night and bragged about how he was in the habit of drinking an entire six-pack every day. He definitely wasn’t my cup of tea, so I ghosted him and blocked him on all of my social media accounts after that fateful date. 

Messy First Date:

On my very first date with a man I met online I was beyond nervous. I kept trying to tell myself I was going to be okay and showed up twenty minutes late because I needed a cigarette. I also had zero idea what this man looked like since this was our first meeting in person. Once I arrived at the café, I walked up to the wrong man, which was incredibly awkward. After texting him outside the café because I was too ashamed to go back in, the man I was supposed to be meeting came out. We walked around and talked about old movies and why he never wanted to get married. He was very kind and after talking for half an hour, he offered to drive me to my friend’s place. At this point, it was 8 p.m. and I hadn’t eaten all day. About halfway to my friend’s house I got this awful nausea, so I asked him to pull over. I got out of the car and started dry heaving. I felt so embarrassed, but he was kind and picked up some water and food for me.

Cold, Wet and Canceled On:

I had a date with a sugar daddy near the end of November. A week earlier he said that I looked beautiful in a dress he bought me and told me to wear the dress on our next date. It just so happened that there was a storm on the night of the date. The dress was flowy and grey, yet still casual. I decided to wear it and got stuck in the storm downtown an hour before I had to meet him. After seeking refuge at a friend’s apartment, I went to meet him for dinner and just as I arrived at the restaurant, he texts me saying he got held up at work and had to cancel. Here I was in an expensive restaurant, soaking wet and runny makeup without a date. 

Love in Transit:

In freshman year, I used to take the bus home every day. I noticed that a guy would take the same route from university and get off at my stop. After a couple of weeks of polite smiles and nods, I introduced myself and we eventually became good friends. One day before we parted ways, he plucked a flower from some poor woman’s garden and asked me if I would want to go out sometime. I laughed and giddily obliged. Looking back, perhaps I should have given it a bit more thought.

We went on a date the following week, and that’s when I realized that he was insufferable. His jokes had always been provocative, but now they were downright racist. I tried my best to bite my tongue, but I found myself pettily bickering with him the whole ride home. We parted ways, me trying not to strangle him, and sat across from each other on the bus in excruciating silence for the rest of the semester.

I learned an important lesson that day — don’t mix romance and transportation, especially when you have no other goddamn way of getting home.

Sushi and Subway:

When I was 16, I went on a date at a sushi place in Kensington. Partway through the meal, he said he wasn’t into the food and stopped eating. I didn’t think anything of it, but I always feel guilty not finishing a meal, so I tried eating as much of it as I could. While we were waiting for the train, I started to feel super woozy and decided I should just go home. We didn’t even make it to 8th Street station before I started throwing up on the train. 

Obviously, something had to be done, so I made an emergency call on the train, and informed them that my emergency was “vomit.” I was pretty delirious, still feeling woozy, and was led by my date to what used to be called “Crackmacs,” and went to the upstairs Subway bathroom to clean myself off. Turns out, the water was broken. My date bought two water bottles from the Mac’s and grabbed some paper towels, which we used outside to clean up to the best of our ability. I managed to get the stains out of my shirt, so I guess it could’ve been worse.


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