Mark Paterson

A few years back a cute girl (who I had a common friend with) added me as a Facebook friend. We chatted and flirted for a few weeks before arranging to meet up for dinner at a nice Sushi bar for what I believed was going to be our first date. To my utter shock and dismay, an hour before we were due to meet up, I received a text from her asking whether I minded if her boyfriend came along to the dinner as well. Needless to say it was the most awkward Sushi experience I have ever had!

Samantha Chiusolo

It was a few months shy of my sweet sixteen. Puck heads and puck bunnies ruled the high school. I was neither. Though I was prodded and pushed to go out with one of these so-called jocks of the ice. He was nice enough, not your typical ‘Moose’, shoving guys into lockers while expelling a farmer’s blow onto the high school hallway.

Dan Christensen

I'd struck out with Casey, my love, but as I was drunkenly lost in Toronto, she let me crash on the couch. So as I watched her clean up my vomit in her bathroom, I thought “this is a record low point” when Joanne, her loud, drunk, and unfortunate-looking roommate, arrived to prove me wrong. Lying in bed, I thought “Whose bed is this?” as I nervously felt a hand creeping up my leg. But who was I to turn Joanne away? Coincidentally, just as things “concluded” I suddenly realized my gaffe and abandoned the scene. I awoke early on the couch to Joanne wanting to talk. I convinced her we should sleep more, then talk. She returned to bed, and I did what any grown man would do: promptly donned my vomit-covered shirt and pants, and deserted for a walk (of shame) to remember.

Helene Goderis

I'd already gone on a few dates with this guy in the summer. He invited me out one night to a magazine launch, where this Asian girl is all over him, asking to crash at his place at the end of the night; he's giving a firm 'no,' but to little effect. Fortunately, I wasn't very taken with him, so I found the situation more amusing than suspect.

Afterwords, we head out on what is loosely a double date at a bar on Ossington. I say 'loosely,' because his attractive male friend accompanied us. There's some jokey sweet talk happening between them, and at points they're sitting on each other's laps.

Last call comes around and we all walk back toward his place. As way of goodbye, this guy friend jumps up and wraps his legs around my date's torso, then in some gymnastic feat, he arches his back and touches his hands to the ground, and then crawls his way back up onto my date. I vaguely remember him not wearing a shirt during this. My date asked me to come inside with him. As the Asian girl from earlier in the night had somehow finagled her way into his bedroom and was laying in wait, I politely declined. The worst part is that I agreed to a couple more dates with him.

Alan Jones

It was 14 November 2006, the day Casino Royale opened. I was on a cultural exchange in Corner Brook, Newfoundland. I went to a party at a residence at Memorial University. I got very drunk. It was not flattering. There was a girl at the back of the dorm living area dancing. For some reason, she was in a bikini top. She asked me how old I was. I said I was twenty. I was actually eighteen. I later found out she was twenty-four.

Later, she put her shirt back on and took me back to her dormitory. We made out. Our teeth bumped a lot. That was my first kiss. Then we disrobed and had intercourse. Judging by her facial expressions, she did not realize I was a virgin. I remember being very disappointed by the sex. It was full of awkward positioning and heavy breathing. I definitely didn’t apply my condom properly. I blame my Catholic high school for that. Afterwards, I left in haste. She still has my belt.

A few weeks later I saw her at another party. I did not make eye contact.

Suzanna Balabuch

February 14th, 2011. After promising to take me to a surprise restaurant, my boyfriend of several months conveniently “forgot” to make a reservation anywhere, and instead took me to Lone Star, his favourite restaurant. He then proceeded to order beer after beer after beer, getting drunk, loud and very grabby. Apparently trying to grab your girlfriend’s ass in a family-friendly restaurant is acceptable behaviour. For some reason he also thought that trying to talk, no, slur dirty to me over burritos was just about the most romantic gesture in the world. I was so incensed by him that I finished my food as quickly as I could, and we walked to Union Station in silence. The silence didn’t last very long though, because once we got to the busiest station in Toronto, he exploded and yelled at me for being too uptight. I turned on my heel and left. Worst Valentine’s ever.

It was a nice winter day, perfect for snowmobiling. I did not have a snowmobile, hence I did not have a snowmobile suit. But for my very first date with a cute boy my adoring parents mustered up one for me. My parents seemed happy as did my match-making friend. The date was set.

Three hours and a broken femur later I’m in an x-ray room pumped full of Demoral being asked by a technician if there is any chance I may be pregnant. I calmly replied, “I’M A VIRGIN!!!”

Geoffrey Vendeville

I haven’t had too many awkward sexual experiences – just enough to last me the rest of my 20s. (Please ignore that last sentence, ladies.)

My worst time involved an Irish gal I met on holiday last summer. She was not much of a looker, but what she lacked in beauty, she made up for in persistence. She would not take “No” or “Let me put my shirt back on, it’s cold outside” for an answer. As we left a bar late one night, she pulled me into a doorway, pinned me against the wall, and thrust her tongue deep down my esophagus. I asked her kindly if she wouldn’t mind trying to kiss my way, but she insisted on kissing “the Irish way” – beer breath, a lot of drool, and teeth-grinding. “It’s getting late, let me walk you back,” I said, gasping for air. Thankfully she agreed. But when we got to her hostel, she turned around and walked me home, subjecting me to a few more wet Irish kisses along the way.

Additional Info

  • Subtitle: the newspaper staff spills their worst hook-up experiences
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