Happy Howl-oween: The Dating Horror Stories Edition!


October is filled with so much (pumpkin) spice. From hiding under blankets while watching horror films with bae to going on Reddit to read endless scary stories that keep us up at night, there’s no shortage of entertainment during this spooky season. 

But nothing can beat the horror that can be the experience of dating. Not to scare you off – as dating can be a fulfilling, fun, joyful experience – but let’s be real, we’ve all had our fair share of dating horror stories.

So, what’s a better month to highlight dating nightmares? Here are 3 spine tingling dating stories that will make you shiver!

1. “Once, I matched with this guy on Dil Mil who lived in Canada. We hit it off right away, and within a few weeks, he was eager to come down to Chicago to meet me in person. So, he booked a flight. On the day of the flight, he called me to let me know his flight had been canceled. He didn’t share much more information and, during our conversation, it sounded like he was canceling the entire trip. Nonetheless, he booked another flight and let me know upon arrival that he was suddenly here. We had a great time together, and even though he planned to only stay for a few days, he ended up staying with me for over a week! When he was visiting, he didn’t hesitate to ask all the serious questions: would I move countries for love? Do I want kids? When do I see myself settling down? The questions were really straightforward and I was taken aback, but I answered! Fast forward to when he returned to Canada, he suddenly ghosted me – responding minimally to my messages, if at all. When I asked him what was going on, he said it’s justified for him not to respond as fast because we live in different countries. The switch ups were so real and so hard to navigate, it all left me confused and stunned!”

– Naomi, Chicago

2. “Showed up 45 min late with no text or call to let me know, just as I was finishing my drink and walking out. He was on the phone with a friend. I went to greet him and he put his hand up in my face to “sshhhh” me. I heard his friend ask “so did you **** her yet?” I loudly said, “No and he won’t either” as I walked out.”

– #7, dating story on medium.com

3. “Many years ago I agreed to meet a lady in a coffee shop for a date. She turns up with 4 screaming kids in tow who climb all over the chairs and just about wreck the place. I paid for our coffees and took my leave lol.”

– #9, dating story on medium.com

Alas, dating in the real world isn’t all fun and games. And while we hopefully swipe waiting to come across our prince charming, some of us sadly do have to kiss some frogs along the way. That being said, sometimes, the best horror stories have the happiest endings! We have no doubt that these stories didn’t work for the better but something great is still waiting for you out there. So good luck this spooky season, keep your head up, and stay safe! 

Get On Dil Mil

Do you have any dating nightmare stories? Send them over to us at jagreet@dilmil.co!


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