Write about a date you went on that took an unexpected turn.

Posted in Nonfiction on Nov 8, 2024

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✍️ 37 stories

“The Skydiving Surprise” by Jim LaFleur

Submitted to Contest #276

There I was, sweating enough to replenish the world’s oceans twice over, sitting across the table from the most adventurous person I had ever met. Let’s call her Ava—because that was her name—and she’d just suggested we head for something “spontaneous” after dinner. Now, when someone says “spontaneous” on a date, I’m thinking coffee shop poetry reading, perhaps roller skating. But this was Ava, whose list of thrills practically included wrestling tornadoes for sport. “Skydiving,” she chirped, eyes sparkling like they’d just been polished wit...

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“Treading water in the dating pool” by Trudy Jas

Submitted to Contest #276

Though the tag indicates "creative non-fiction, the tale is sadly true. A date is more than “didchaeatyet?’ right. Let's say a date is an event where the dator askes the datee, then picks up said datee and brings the datee home again. And you want to know if any of mine ever took a left turn, right? Yeah, sure. No problem. Except which one shall I share with you? Oh never, mind. I’ll tell you about all of them. Take a seat. No, this won’t take long. It’s a short story, more like flash fiction, really.It was in tenth grade that Robert as...

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“Me & Mel” by Kate Simkins

Submitted to Contest #276

It was when Melvin turned to one side and casually vomited on the floor of the pub that I realised the date wasn’t going to end as I had hoped. There was no way I wanted a first kiss after that. But maybe I should start at the beginning because actually, it all began rather well. There had been rumblings of a future for me and Mel since we met at the ABC cinema in Lancaster a few weeks before the ill-fated, vomit-filled adventure of our first date. I had taken on (another) part-time job to help fund my extravagant student lifestyle (...

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“Caroline, I Think” by KA James

Submitted to Contest #276

My sister-in-law got a conversation starter card game from a Secret Santa gift exchange at work, and it seemed that the family was going to have to suffer the consequences.It was the holiday season a few Christmases ago. OK, quite a few years back. Since the family was all mostly gathered in town already, we were having a pre-Christmas get together at my brother’s house. All the kids were in bed, or at least upstairs, and the adults were sitting up just drinking and bullshitting, when sister-in-law Debbie pulled out her new game.Skipping ahe...

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“chewing the fat” by Rebecca Detti

Submitted to Contest #276

‘Morning honey’ ‘Oh, Morning boys’ I said to my gym buddies, Richard, Mark and Alan. All three chaps were retired and the fittest looking septuagenarians I had ever seen. Seriously athletic.After the school run, I love nothing more than going to my local council-run gym, the 'Better gym'. What a great name. It definitely does what it says on the tin as my dad likes to say. It felt like such a release getting back into the gym after years of disjointed exercise that comes with having a baby and not putting yourself first, but I was ...

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“Dunkelflaute” by Rebecca Hurst

Submitted to Contest #276

There is a woman in my village called Moira who pulls a little dog around on a lead. The dog is joyous. Moira is not. Nothing pleases her and so, over the years, I have adopted a bonhomie which I know she finds irritating. She has three grown-up children, none of whom speak to her. This does not surprise me, because Moira is inherently sour, and she often asks me pointedly how my son is doing. She has never met him, but I once told her that he occasionally smoked weed and in her mind, this makes me a bad mother. My son speaks to me thou...

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“There'll be Another One Along in a Minute” by Carol Stewart

Submitted to Contest #276

I was in Princes Street, Edinburgh when I met him.‘Hello,’ he said, ‘Are you waiting on a bus?’And there was me thinking I was playing Sudoku with the numbers on the overhead sign.‘Oh, shoot, oh no, what am I saying? Of course you are, I’m sorry.’Well, wasn’t he the perfect little mannerly gent in his private school blazer and tie? And was that a ‘Vote Conservative’ badge on his lapel? Oh my god, another Colin…Little Colin ------- windsor-knotted uptight, leather briefcase in hand and forever quoting Maggie Thatcher. In fact, in those last f...

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“June 10th, 2020” by Haylee Hemphill

Submitted to Contest #276

**Sensitive Content: Mental Health, Alcohol, Major Bodily Injuries Abandoning solitude of many months. I found myself risking peace. I had finally decided to break free from the labyrinth of my mind and the safety of my bedroom. I was going to go on what felt like my first date. It was not, I just had not let myself be a real human being for months now and it was like I forgot how to function. “You can do it. You are overthinking it. It’s going to be okay, just do it!” My own voice in my head gives me a pep talk while my body is sha...

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“Soulsaving virginity” by Dzhamilia Gasanova

Submitted to Contest #276

As if the night had come too early, the spring darkness of Kyiv was heavy and damp. Wet from the constant rain, the streets were still deserted, but alive with the downpours, the wind that yawned on our skin, and the wet shoes that vibrated on the sidewalk.He was tall and walked beside me. It was our first date. His shoulders were slightly hunched, as if he had a habit of defending himself. The black, wet coat seemed too wide. His curly brown curls clung to his caramel skull, and the rain dripped from his hair in almost a trickle. He had the...

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“Pieces of the Puzzle” by Lindsay Nicole

Submitted to Contest #276

Thursday Night Avery leaned back in her chair, the flickering glow of her laptop screen casting soft shadows across her tired face. The online dating world had been a series of disappointments. There was Ryan, who had seemed perfect in his profile photo—until their date, when he spent the entire time texting someone else under the table. Then there was Derek, who liked to call himself “adventurous” but considered a “night out” to be watching reruns of Game of Thrones while guzzling beer. And, of course, there was Caleb, who had promised her ...

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“Turned out to be the best first date ever” by Kathryn Lester

Submitted to Contest #276

I had recently broken up with my long-term boyfriend for a multitude or reasons, but my mother eloquently put it as, "You were just incompatible in every way that counted", which was true, but unfortunate that it took me two years to figure that out. Anyways, I was not really looking for anything specific after such a fresh break-up, so, I decided to download Tinder because, well, why not? There were tons of weirdos on Tinder and after the most recent Tinder match informed me that he was missing ALL of his teeth and asking how I would feel k...

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“Moonlight Mischief ” by Aaron Schuck

Submitted to Contest #276

In my early twenties, I was known as the guy who could take a normal date and turn it into an unpredictable adventure. I wasn’t much for conventional romance—the fancy dinners, the thoughtful gifts. I thrived on surprise, the thrill of doing something a little offbeat. So, one night when I found myself on a date that was going particularly well, I decided to push the limits and see just how spontaneous things could get.The night started out straightforward enough. I’d picked a small Italian restaurant tucked away in a quieter part of town. I...

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“An Apathy Sharper Than Hatred” by Mallory Jones

Submitted to Contest #276

“I love you… like, not as a friend. I’m in love with you. I’ve been in love with you for years. I followed you here because I couldn’t imagine life without you. I like you as more than a friend. I really— damn it!” Margo put her face in her hands and the mirror mimicked the motion. This was going to be a disaster. How could she possibly convey how she felt to Christine if she couldn’t even do it alone in the bathroom? There were only a couple minutes left to practice. She took a deep breath, and locked eyes with herself in the mirr...

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“Gumby Girl” by Michael Jefferson

Submitted to Contest #276

In my early twenties, I developed a talent for avoiding adult relationships in favor of having fun. My relationship with Kacey Jones (yeah, her parents were real comedians) was the zenith of my good-time Charlie way of life. Kacey was part of a group of party girls of all sizes, shapes, ages, and nationalities who came to the park to watch our softball games. We dubbed our cheerleaders the Pound Ridge Comedy. Kacey was my favorite, a 4’ 11” pneumatic blonde who wore nothing and blissfully knew nothing. She was a cutie in a constant st...

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“Slightly Charred” by Alex Kamczyc

Submitted to Contest #276

To the broke, unmotivated and hopeless college kid with no job, something like cooking your own meal can be trivial. On a good week, you’d get anywhere between 30 and 50 bucks that you’d need to stretch for the whole month. You could spend that on chicken, fresh veggies and pasta. Of course, Taco Bell is right down the street and a box of ramen is a buck fifty - which means you can buy a few cases of beer on the weekends if you need to. This was my life at Kent State University in gloomy Kent, Ohio, and aside from studying journalism and wri...

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Write about a date you went on that took an unexpected turn.

Submissions are closed

✍️ 37 stories

“The Skydiving Surprise” by Jim LaFleur

“Treading water in the dating pool” by Trudy Jas

“Me & Mel” by Kate Simkins

“Caroline, I Think” by KA James

“chewing the fat” by Rebecca Detti

“Dunkelflaute” by Rebecca Hurst

“There'll be Another One Along in a Minute” by Carol Stewart

“June 10th, 2020” by Haylee Hemphill

“Soulsaving virginity” by Dzhamilia Gasanova

“Pieces of the Puzzle” by Lindsay Nicole

“Turned out to be the best first date ever” by Kathryn Lester

“Moonlight Mischief ” by Aaron Schuck

“An Apathy Sharper Than Hatred” by Mallory Jones

“Gumby Girl” by Michael Jefferson

“Slightly Charred” by Alex Kamczyc

🌟 Similar prompts

Write about an encounter with someone new to you who changed your life forever.

Write about something you do now that has become routine, but that the old you — or friends and family from your past — would never believe if they couldn’t witness it today with their own eyes.

Write about a relationship or friendship that was unexpected or so outside your usual type that you kept it a secret from your loved ones. (Bonus points if it didn’t stay secret for long!)

Write about a time you approached a situation with one strong feeling or belief, only to have your perspective shift completely by the end.

Contest #276

Enter our weekly contest!

$250

Prize money

230

Contest entries

110

Stories

Win $250 in our short story competition 🏆

Explore more writing prompt ideas: