‘Tis the season to be awkward: 11 staffers and fashion folks share their strangest holiday stories

We’ve always thought the holidays were kind of strange. The entire month of December, actually, is pretty odd. We’re expected to be jolly and joyful for all 31 days of it, and yet the reality is that it’s just cold, busy and crowded. There’s a lot of small talk involved, and nothing ever goes exactly as planned. It’s not that we don’t like the holidays, we just don’t like the pressure to have fun that comes with them. So in the spirit of “WTF,” we asked our editors and other insiders to share their strangest holiday stories.

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“This is not a photo of me at Christmas, it is a photo of me on my birthday, which is around Christmas. It’s important to note the cake and sparklers and general happy aura of the photo because none of those things were present a couple of Christmases ago. My family and I had decided to, rather than exchange presents with everyone, do a Secret Santa exchange. Fun, right? One. Would. Think.

Being the organizer that I am, I gathered us all together months before Christmas so we could choose names out of a hat, and after many, many tries (someone always ended up picking their own name and we’d have to start over), we each had someone to buy for. Throughout the next few weeks, I sent my family texts to remind them to buy thoughtful, personal gifts. Then finally, on Christmas Eve, the gift exchanged happened. Everyone picked up a gift with their name on it and watched patiently as I searched for mine and…nothing.

Turns out, due to the several attempts of pulling names back in October, there had been a mix-up and the person who eventually picked my name um, forgot. And so, the organizer was left without a gift. Womp womp.”

Souzan Michael, Associate Digital Editor, fashionmagazine.com

“A few years ago, there was a crazy massive snowstorm the day we had plans to celebrate Christmas with my husband’s family. We had to drive from downtown Toronto to the suburbs, while everyone else attending the party lived only a few minutes away from where it was being held. Most people would have cancelled their plans and stayed home, but my mother-in-law was adamant that we be there.

Highlight reel: SO much swearing and tires spinning out. But the best part was when we had to push the car up a ramp to get onto the DVP, as snow pelted our faces causing my mascara run down my cheeks. It took us two hours to get there. We arrived expecting everyone’s sympathy, but no one seemed to care, including my mother-in-law, who was annoyed that we were late.”

Sarah Daniel, Beauty Editor, FASHION Magazine

My husband and I were at a holiday party a couple of years ago. The host was a bit of a ‘man about town’: lived in a gorgeous condo, expensive art everywhere, catering by top local company, everyone done up to the nines. Neither my husband nor I knew many people at the party, and when I decided to go touch up my lipstick, my husband came along to the powder room.

He sat down on the floating vanity while I rummaged in my purse for my red lipstick, and as I looked up to re-apply, my husband—and the vanity—came crashing down onto the gorgeously expensive marble floor. Guests began knocking at the door, asking what was going on, and eventually after deciding that we could not flush ourselves down the toilet, my husband had to (sheepishly) bring the condo owner/party thrower into the washroom to help him carry out (into the waiting crowd) the no-longer-floating vanity, while I picked up pieces of broken stone from the floor in my cocktail dress and heels.

We did stay for one more HUGE glass of wine before leaving and never looking back. Epic fail.

Samantha Diamond, Executive Director, ROI Relations

“I seem to avoid the dreaded fear of being in transit at midnight by about three minutes every year. Last year, we made a cab driver wait for us to watch the ball drop before heading to the bar and I honestly have no idea how long he was waiting there.”

Randi Bergman, Executive Digital Editor, fashionmagazine.com

“2004 marked my first legal-to-drink holiday party, so I celebrated not just by wearing my prom dress from the year before, but by going with three friends who vowed to make this Rona Home & Garden soirée legendary.

It started right: I arrived and walked up to the bar for a cosmopolitan. The bartender didn’t know what that was (LOL, such a Charlotte), so I gave her step-by-step instructions: two shots of this, two of that, and one of that orange-y stuff . . . maybe add another. And then I had three more.

I became a picture of grace and elegance. Convinced I was Cambridge’s answer to Carrie Bradshaw, I sashayed my way onto the empty dance floor, declaring that tracks by Def Leppard, Joan Jett, and Christina Aguilera were “MY SONG!” before falling out of my shoes. Then I sat down at my managers’ table and compared everybody’s wives to Sex and the City characters. And I took photos of myself holding my swamp water, proud that no one could tell I was drunk. “THIS IS THE BEST!” I yelled, to embarrassed faces. “I LOVE YOU!”

We left at midnight and I rolled into bed, convinced I would not only be in tip-top shape for my 7 45 a.m. shift the next morning, but that I’d set a record for being the most fun and classy attendee. (Who had to put her foot on the wall to make the room stop spinning.) Then, 7 a.m. soon came, and I crawled to the bathroom, where I prepared for my four-hour shift spent with my head on the counter, fielding questions from my coworkers like, “Def Leppard, eh?” and “Did you really compare Greg’s wife to Miranda because she had red hair?”

I don’t know. Maybe. But the important thing is, if you need to throw up in a Rona Home & Garden, let me know because I, courtesy of the mental maps I made that day, now know the fastest ways to get to where that can happen discreetly. Let’s see Carrie Bradshaw do that.”

Anne T. Donahue, Freelance Writer

“The very first holiday that I spent with my husband’s family, I received a hair removal system. I’m northern European and really not a hairy person…or so I thought!”

Christina Walters-Arseneau, Senior Account Manager, rock-it promotions, inc.

“My craziest holiday was the year my mother had a stroke as I was taking the turkey out of the oven. I invited everyone to the dining room table, she stood up and collapsed. I called 911 and the house quickly filled with firemen and paramedics. My husband, meanwhile, was making gravy and unstuffing the bird, not wanting all our hard work to go to waste.

My twin boys, who were three months old, also needed to be fed. The paramedics took my mom to the hospital and my dad went with them. I fed the rest of the crowd and soon followed. My mother survived that episode and lived another 11 years. I have bought Christmas dinner from a caterer ever since.”

Bernadette Morra, Editor-in-Chief, FASHION Magazine

“In my twenties I got the travel bug, quit my job and moved to Japan to teach English. This was my chance to see the world, and since I was far from family I decided to spend Christmas in Southeast Asia with a fellow English teacher. He was fluent in three languages, had several study abroad programs under his belt, and seemed the perfect travel companion.

But as soon as we got off the plane, he grew condescending and dismissive of my travel suggestions. We spent Christmas with a friend of his in a city I didn’t want to be in, so on Boxing Day I left for a beach setting (cliché, but I was 26!). My friend joined me for a few days, partly out of duty, but when he decided to travel elsewhere I stood on the beach and waved goodbye as he boarded a wood pontoon.

I always travelled solo after that (until I met my husband many years later). I still value what I learned about myself from that friend, and he is still a friend, but now lives in a war-torn country and works for an NGO.”

Jacquelyn Francis, Executive Editor, FASHION Magazine

“I was party-hopping one New Years and ended up at this private event on Queen Street West, I started chatting with this guy and realized that we knew each other through work but had only ever communicated over email. We had never met in person until that night.

We immediately started jabbing each other and I (sort of) mistakenly kicked him with my big Alexander McQueen heel. He was totally surprised and not impressed. I went off to another party and later on he became my boyfriend of three and a half years. We broke up a couple years ago but now we’re best friends!”

Julia Che, Founder & CEO of Lotus Leaf Communications

“When I was 11/12 years old, for Christmas I asked my parents for a small TV for my bedroom. I had a specific model in mind – I saw it in a London Drugs flyer (of all places).

Once all the gifts were laid out under the tree, I thought that I spotted it (perfect size, shape, etc.) I couldn’t believe that my parents had bought it for me! On Christmas morning, all eyes were on me as I went to unwrap the present. I kept it for last. I picked it up and thought that it was a bit heavier than expected.

To my dismay, it wasn’t a TV, it was a set of giant black dumbbells. I didn’t work out so this made no sense. I couldn’t hide my disappointment and to this day am convinced that they were actually for my brother (my mom is notorious for mislabeling gifts). My dad still uses the dumbbells, though.”

Delphine Nicholls, Executive Director, ROI Relations

“A few years back, a friend and I decide to take a last minute road trip to New York to celebrate New Year’s Eve. She knew someone who had recently moved to NYC and he had generously offered to let us stay at his apartment for the weekend. New York City for New Year’s Eve and a free place stay? Sign me up. Hours of driving later, we finally arrived at “Matt’s” apartment.

We hit up a local sushi restaurant for dinner. A few hours into to dinner, my friend became violently ill from what we now know to be a severe allergic reaction to avocado. Of course, I quickly rushed my friend into a cab and back to the apartment, leaving Matt to continue on the night with friends. After hours of tending to my friend, she eventually fell asleep in Matt’s bed. I fell asleep on the living room couch.

Hours later, I woke up to the sound of Matt coming home from his night out and poured us two very large glasses of red wine. He proceeded to light a few candles and then move over to his iPod dock, shuffling through his playlists until he finds a compilation of Motown oldies. Yes, Motown oldies. I’m talking Stevie Wonder and The Temptations.

At that point I realized he is trying (and failing) to set the mood. I was still trying to process how to get out of this situation when Matt leaned over to kiss me. In sheer panic, I blocked him with my wine glass, spilling red wine literally all over him and his couch. At that point, he obviously got the hint. We both awkwardly grabbed a couple paper towels, cleaned up the mess (without speaking) and he hurried to bed.

Needless to say, when the clock struck 12 on New Years Eve the next night, and everyone else was scoping out their midnight kiss, I was hiding, trying to avoid a repeat attempt from Matt.”

Alyssa Whited, Public Relations Specialist, ROI Relations

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