Dating Disaster Stories

Do you have a dating disaster story to share with us?

I have heard many funny, interesting and down right peculiar dating stories from friends, clients or readers from this site. Here are a couple of examples to get things started.

Valentine’s Day Massacre

“I dated the least romantic guy on the planet. He invited me to dinner and a movie for Valentine’s Day which has always been a really big deal for me. The movie started at 9.30pm, so I arrived at his house all dolled up and ready to go at 6.30pm only to find him buried under his car, up to his ears in oil and dirt. Apparently, he’d decided that night was as good as any to fix up his car. I waited patiently for two hours but by 8.30pm my patience was wearing thin. He showered and dressed but still smelled like an old oily rag and then drove us through the McDonalds’ drive through for our meal before making our way to the cinema. He hadn’t booked, and the only movie with available tickets was Hannibal, (no surprise there, who the hell goes to see a movie about cannibalism on Valentine’s Day?). We sat through two hours of blood and gore. It was the worst date I’ve ever been on.” - Gemma

Cringe factor

“Craig and I met through mutual friends and we instantly hit it off. Knowing my passion for wine he organised a winery tour for our first date. The first half of the day was fantastic, until our tour bus pulled up at the last winery.

There was a long queue for the tasting and the rain had started to fall. I was feeling so warm and fuzzy inside I’d failed to notice a shift in Craig’s behaviour. He stood in line drumming his fingers against his legs scowling at the person in front of us, and muttering under his breath. I snuggled closer to him and asked what was wrong and out came the onslaught.

He began yelling at the person in front of us for jumping the queue, (the tour operator for the delay), before cursing the sky above for the rain. My fantasy guy had turned into a prick before my eyes. I cringed with embarrassment; he had made an ass of himself and me and I dreaded the long bus ride home.

Rude guys are a major turn-off, they’re just no fun to be around. Funnily enough Craig couldn’t understand why I didn’t want to see him again.” - Tina

The once over

“I met Grant online and after a week of flirting we agreed to meet at a local café. He was really cute and exactly the way he’d described himself, which was a huge tick in my book. After knowing each other for less than a minute, he looked me up and down, making a verbal commentary as he went, ‘Nice long legs, nice ass, yeah good rack, great smile, mmm, lovely.’ I felt like a prostitute and was really insulted, I didn’t realise that I’d given him the impression that I was easy.” - Suzanne

Feel free to add your own story or maybe someone you know, but please make sure your story is original and please write over 100 words for me to put up the page.

Do you have a worse dating disaster story?

I am trying to look for the worst dating disaster story, so try your best!!

Enter Your Title

Tell Us Your Story! [ ? ]

Author Information (optional)

To receive credit as the author, enter your information below.

Your Name

(first or full name)

Your Location

(ex. City, State, Country)

Submit Your Contribution

Check box to agree to these submission guidelines.


(You can preview and edit on the next page)